Tokushima University / Educator and Researcher Directory --- Nakao, Michiyasu

Personal Web Page

https://researchmap.jp/m-nakao (researchmap)

Field of Study

○	Pharmacy

Subject of Study

○	有機化学

Book / Paper

Academic Paper (Judged Full Paper):

1.	Michiyasu Nakao, Akihito Nakamura, Shoki Yamada, Syuji Kitaike and Shigeki Sano : Concentration-dependence of specific rotation of optically active glycerol analogues and structurally related compounds: The significance of intermolecular hydrogen bonding, Results in Chemistry, Vol.7, 101415--, 2024. (Summary) Specific rotation of optically active glycerol analogues, (S)-3-(benzyloxy)propane-1,2-diol [(S)-1], (S)-3-methoxypropane-1,2-diol [(S)-6] and (S)-3-phenoxypropane-1,2-diol [(S)-13], changed its sign from (+) to () with increasing concentration in CHCl3, whereas no significant concentration-dependent change was observed in MeOH. The 1H NMR spectrum of (S)-1 showed concentration-dependent changes of the chemical shift in CDCl3. Intermolecular interaction by OHOH hydrogen bonds was suggested by single crystal X-ray crystallography of (S)-13. The concentration-dependent changes of specific rotation of (S)-1, (S)-6, and (S)-13 in CHCl3 can therefore be presumed to be due to self-assembly of these compounds via intermolecular hydrogen bonding at high concentration. The remarkable concentration-dependent changes in specific rotation were also observed to occur in the compounds with related chemical structures, such as (S)-3-hydroxy-4-methoxy-4-oxobutanoic acid [(S)-10], (S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid [Boc-L-Pro-OH, (S)-14], (R)-3-hydroxy-4,4-dimethylhydrofran-2(3H)-one [(R)-15], (R)-tetrahydrofuran-2-carboxylic acid [(R)-16], (S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid [Boc-L-Val-OH, (S)-17], (R)-oxiran-2-ylmethanol [(R)-18], and (4S)-4-isopropyloxazolidin-2-one [(S)-19]. The existence of intermolecular interaction by C=OHO hydrogen bonds was suggested by single crystal X-ray crystallography of (S)-10, (S)-13, and (S)-14. Thus, this series of chiral compounds have multiple functional groups in appropriate positions that serve as hydrogen-bond donors and/or acceptors, resulting in significant concentration-dependent changes of specific rotation. (Keyword) glycerol / intermolecular hydrogen bonding / concentration dependence / specific rotation / 1H NMR spectroscopy / X-ray crystallography (Tokushima University Institutional Repository) ● Metadata: 119086 (Link to Publication Site) ● Publication site (DOI): 10.1016/j.rechem.2024.101415 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1050299595812169728 ● Summary page in Scopus @ Elsevier: 2-s2.0-85187313350 (Tokushima University Institutional Repository: 119086, DOI: 10.1016/j.rechem.2024.101415, CiNii: 1050299595812169728, Elsevier: Scopus)
2.	Michiyasu Nakao, Akihito Nakamura, Tomoyuki Takesue, Syuji Kitaike, Hiro-O Ito and Shigeki Sano : Synthesis of Novel Phosphorus-Substituted Stable Isoindoles by a Three-Component Coupling Reaction of ortho-Phthalaldehyde, 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide, and Primary Amines, SynOpen, Vol.7, No.3, 394-400, 2023. (Summary) A three-component coupling reaction of ortho-phthalaldehyde, 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide, and various primary amines readily afforded novel phosphorus-substituted stable isoindoles in good to excellent yields. The importance of the reversible ring-opening of 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide by methanolysis in the three-component coupling reaction became apparent. (Keyword) OPA method / isoindoles / ortho-phthalaldehyde / 9,10-dihydro-9- oxa-10-phosphaphenanthrene 10-oxide / primary amines / isoindolin-1-ones / ring-opening / methanolysis (Tokushima University Institutional Repository) ● Metadata: 118534 (Link to Publication Site) ● Publication site (DOI): 10.1055/a-2148-9433 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-85170846368 (Tokushima University Institutional Repository: 118534, DOI: 10.1055/a-2148-9433, Elsevier: Scopus)
3.	Michiyasu Nakao, Ken Horikoshi, Syuji Kitaike and Shigeki Sano : Efficient One-Pot, Three-Step Synthesis of 1,2,3,5-Tetrasubstituted Pyrroles via Aza-Michael Addition of Methyl 3-Iminoacrylates, Heterocycles, Vol.106, No.8, 1397-1406, 2023. (Summary) An efficient one-pot, three-step procedure for the aza-Michael addition of methyl 3-iminoacrylates with secondary amines followed by intramolecular cyclization and silylation successfully afforded novel 1,2,3,5-tetrasubstituted pyrroles in high yields. (Keyword) aza-Michael addition / 1,4,5-trisubstituted 1,3-dihydro-2H-pyrrol-2-one / 1,2,3,5-tetrasubstituted pyrrole / methyl 3-iminoacrylate / one-pot reaction (Tokushima University Institutional Repository) ● Metadata: 118458 (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-23-14876 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.3987/COM-23-14876 (Tokushima University Institutional Repository: 118458, DOI: 10.3987/COM-23-14876)
4.	Takeshi Harada, Hiroto Ohguchi, Asuka Oda, Michiyasu Nakao, Jumpei Teramachi, Masahiro Hiasa, Ryohei Sumitani, Masahiro Oura, Kimiko Sogabe, Tomoko Maruhashi, Mamiko Takahashi, Shiroh Fujii, Shingen Nakamura, Hirokazu Miki, Kumiko Kagawa, Shuji Ozaki, Shigeki Sano, Teru Hideshima and Masahiro Abe : Novel antimyeloma therapeutic option with inhibition of the HDAC1-IRF4 axis and PIM kinase, Blood Advances, Vol.7, No.6, 1019-1032, 2023. (Summary) Multiple myeloma (MM) preferentially expands and acquires drug resistance in the bone marrow (BM). We herein examined the role of histone deacetylase 1 (HDAC1) in the constitutive activation of the master transcription factor IRF4 and the prosurvival mediator PIM2 kinase in MM cells. The knockdown or inhibition of HDAC1 by the class I HDAC inhibitor MS-275 reduced the basal expression of IRF4 and PIM2 in MM cells. Mechanistically, the inhibition of HDAC1 decreased IRF4 transcription through histone hyperacetylation and inhibiting the recruitment of RNA polymerase II at the IRF4 locus, thereby reducing IRF4-targeting genes, including PIM2. In addition to the transcriptional regulation of PIM2 by the HDAC1-IRF4 axis, PIM2 was markedly upregulated by external stimuli from BM stromal cells and interleukin-6 (IL-6). Upregulated PIM2 contributed to the attenuation of the cytotoxic effects of MS-275. Class I HDAC and PIM kinase inhibitors cooperatively suppressed MM cell growth in the presence of IL-6 and in vivo. Therefore, the present results demonstrate the potential of the simultaneous targeting of the intrinsic HDAC1-IRF4 axis plus externally activated PIM2 as an efficient therapeutic option for MM fostered in the BM. (Keyword) Histone Deacetylase 1 / Interleukin-6 / Benzamides / Pyridines (Tokushima University Institutional Repository) ● Metadata: 118211 (Link to Publication Site) ● Publication site (DOI): 10.1182/bloodadvances.2022007155 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 36129197 ● Search Scopus @ Elsevier (PMID): 36129197 ● Search Scopus @ Elsevier (DOI): 10.1182/bloodadvances.2022007155 (Tokushima University Institutional Repository: 118211, DOI: 10.1182/bloodadvances.2022007155, PubMed: 36129197)
5.	Ray Nath Manobendro, Mizune Ohzono, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : Only one carbon difference determines the pro-apoptotic activity of α-tocopheryl esters, The FEBS Journal, Vol.290, 1027-1048, 2023. (Summary) α-Tocopheryl succinate (TS), a redox-silent succinyl ester of natural α-Tocopherol, has emerged as a novel anti-cancer agent. However, the underlying mechanism is unclear. We found that the terminal dicarboxylic moiety of tocopheryl esters contributes to apoptosis induction and thus cytotoxicity. To further examine this relationship, we compared the pro-apoptotic activity of TS, which has four carbon atoms in the terminal dicarboxylic moiety, to that of a newly synthesized, tocopheryl glutarate (Tglu), which has five. Cytotoxicity assays in vitro confirmed that TS stimulated apoptosis, while Tglu was non-cytotoxic. In investigating biological mechanisms leading to these opposing effects, we found that TS caused an elevation of intracellular superoxide, but Tglu did not. TS increased intracellular Ca in cultured cells, suggesting induction of endoplasmic reticulum (ER) stress; however, Tglu did not affect Ca homeostasis. 1,4,5-trisphosphate (IP ) receptor antagonist 2-Aminoethyl diphenylborinate (2-APB) decreased TS-induced intracellular Ca , restored mitochondrial activity and cell viability in TS-treated cells, establishing the ER-mitochondria relationship in apoptosis induction. Moreover, real-time PCR, immunostaining and Western blotting assays revealed that TS downregulated glucose-regulated protein 78 (GRP78), which maintains ER homeostasis and promotes cell survival. Conversely, Tglu upregulates GRP78. Taken together, our results suggest a model in which TS-mediated superoxide production and GRP78 inhibition induce ER stress, which elevates intracellular Ca and depolarizes mitochondria, leading to apoptosis. Because Tglu does not affect superoxide generation and increases GRP78 expression, it inhibits ER stress and is thereby non-cytotoxic. Our research provides insight into the structure-activity relationship of tocopheryl esters regarding the induction of apoptosis. (Tokushima University Institutional Repository) ● Metadata: 117788 (Link to Publication Site) ● Publication site (DOI): 10.1111/febs.16623 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 36083714 ● Summary page in Scopus @ Elsevier: 2-s2.0-85138289941 (Tokushima University Institutional Repository: 117788, DOI: 10.1111/febs.16623, PubMed: 36083714, Elsevier: Scopus)
6.	Morito Katsuya, Shimizu Ryota, Ali Hanif, Shimada Akina, Miyazaki Tohru, Takahashi Naoko, Rahman Motiur M., Tsuji Kazuki, Shimozawa Nobuyuki, Michiyasu Nakao, Shigeki Sano, Momoyo Azuma, Nanjundan Meera, Kentaro Kogure and Tamotsu Tanaka : Molecular species profiles of plasma ceramides in different clinical types of X-linked adrenoleukodystrophy, The Journal of Medical Investigation : JMI, Vol.70, No.3.4, 403-410, 2023. (Summary) X-linked adrenoleukodystrophy (X-ALD) is a genetic disorder associated with peroxisomal dysfunction. Patients with this rare disease accumulate very long-chain fatty acids (VLCFAs) in their bodies because of impairment of peroxisomal VLCFA ?-oxidation. Several clinical types of X-ALD, ranging from mild (axonopathy in the spinal cord) to severe (cerebral demyelination), are known. However, the molecular basis for this phenotypic variability remains largely unknown. In this study, we determined plasma ceramide (CER) profile using liquid chromatography-tandem mass spectrometry. We characterized the molecular species profile of CER in the plasma of patients with mild (adrenomyeloneuropathy;AMN) and severe (cerebral) X-ALD. Eleven X-ALD patients (five cerebral, five AMN, and one carrier) and 10 healthy volunteers participated in this study. Elevation of C26:0 CER was found to be a common feature regardless of the clinical types. The level of C26:1 CER was significantly higher in AMN but not in cerebral type, than that in healthy controls. The C26:1 CER level in the cerebral type was significantly lower than that in the AMN type. These results suggest that a high level of C26:0 CER, along with a control level of C26:1 CER, is a characteristic feature of the cerebral type X-ALD. J. Med. Invest. 70 : 403-410, August, 2023. (Keyword) Humans / Adrenoleukodystrophy / Ceramides (Tokushima University Institutional Repository) ● Metadata: 118324 (Link to Publication Site) ● Publication site (DOI): 10.2152/jmi.70.403 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 37940524 ● Search Scopus @ Elsevier (PMID): 37940524 ● Search Scopus @ Elsevier (DOI): 10.2152/jmi.70.403 (Tokushima University Institutional Repository: 118324, DOI: 10.2152/jmi.70.403, PubMed: 37940524)
7.	Misaki Yamasaki, Yuika Seto, Mizune Ohzono, Michiyasu Nakao, Akira Shigenaga, Akira Otaka, Shigeki Sano and Kentaro Kogure : Development of a novel tocopheryl ester for suppression of lipid accumulation without cytotoxicity by optimization of dicarboxylic ester moiety, Biochemistry and Biophysics Reports, Vol.31, 101329, 2022. (Tokushima University Institutional Repository) ● Metadata: 117361 (Link to Publication Site) ● Publication site (DOI): 10.1016/j.bbrep.2022.101329 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1016/j.bbrep.2022.101329 (Tokushima University Institutional Repository: 117361, DOI: 10.1016/j.bbrep.2022.101329)
8.	Michiyasu Nakao, Munehisa Toguchi, Ken Horikoshi, Syuji Kitaike and Shigeki Sano : Synthesis of Novel 2,3-Disubstituted Thiophenes via Tandem Thia-Michael/Aldol Reaction of Allenyl Esters, Heterocycles, Vol.104, No.2, 379-388, 2022. (Summary) A tandem thia-Michael/aldol reaction of allenyl esters and mercaptoacetaldehyde in the presence of triethylamine provided 2,3,4-trisubstituted tetrahydrothiophenes. Novel 2,3-disubstituted thiophenes were obtained in high yield by the subsequent dehydration of the 2,3,4-trisubstituted tetrahydrothiophenes using p-toluenesulfonic acid monohydrate as an effective catalyst. (Keyword) thia-Michael/aldol reaction / 2,3,4-trisubstituted tetrahydrothiophene / 2,3-disubstituted thiophene / allenyl ester / 1,4-dithiane-2,5-diol (Tokushima University Institutional Repository) ● Metadata: 117165 (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-21-14575 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.3987/COM-21-14575 (Tokushima University Institutional Repository: 117165, DOI: 10.3987/COM-21-14575)
9.	Michiyasu Nakao, Tomomi Shozui, Daisuke Inoue, Takahito Ihara, Syuji Kitaike and Shigeki Sano : Catalytic Asymmetric Ring-Opening of σ-Symmetric Cyclic Carbonates with Chiral Sulfonamide-Amine Catalysts, Heterocycles, Vol.103, No.2, 1011-1022, 2021. (Summary) Enantioselective ring-opening of σ-symmetric six-membered cyclic carbonates with benzyl alcohol catalyzed by 20 mol% of chiral amino sulfonamide catalysts afforded chiral acyclic carbonates in up to 79% ee. (Keyword) Ring opening / Cyclic carbonate / Chiral amino sulfonamide / asymmetric synthesis / organocatalysts (Tokushima University Institutional Repository) ● Metadata: 116119 (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-20-S(K)42 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.3987/COM-20-S(K)42 (Tokushima University Institutional Repository: 116119, DOI: 10.3987/COM-20-S(K)42)
10.	Shota Fuimoto, Naoki Muguruma, Michiyasu Nakao, Hidenori ANDO, Takanori Kashihara, Yoshihiko Miyamoto, Koichi Okamoto, Shigeki Sano, Tatsuhiro Ishida, Yasushi Sato and Tetsuji Takayama : Indocyanine green-labeled dasatinib as a new fluorescent probe for molecular imaging of gastrointestinal stromal tumors., Journal of Gastroenterology and Hepatology, Vol.36, No.5, 1253-1262, 2020. (Summary) It is difficult to differentiate gastrointestinal stromal tumors (GISTs) from other subepithelial lesions under gastrointestinal endoscopy. Because most GISTs express tyrosine kinase receptor c-KIT, fluorescence-labeled c-KIT-specific tyrosine kinase inhibitors seem to be useful agents for molecular imaging of GIST. We aimed to develop a near-infrared fluorescent imaging technology for GIST targeting c-KIT using the novel fluorescent probe indocyanine green-labeled dasatinib (ICG-dasatinib) and to investigate the antitumor effect of ICG-dasatinib on GIST cells. Indocyanine green-labeled dasatinib was synthesized by labeling linker-induced dasatinib with ICG derivative 3-indocyanine-green-acyl-1,3-thiazolidine-2-thione. Human GIST cell lines GIST-T1 and GIST-882M were incubated with ICG-dasatinib and observed by fluorescent microscopy. GIST cells were incubated with ICG-dasatinib, unlabeled dasatinib, or imatinib, and cell viabilities were evaluated. Subcutaneous GIST model mice or orthotopic GIST model rats were intravenously injected with ICG-dasatinib and observed using an IVIS Spectrum. Strong fluorescent signals of ICG-dasatinib were observed in both GIST cell lines in vitro. IC50 values for ICG-dasatinib, unlabeled dasatinib, and imatinib were 13.9, 1.17, and 16.2 nM in GIST-T1 and 26.6, 3.63, and 47.6 nM in GIST-882M cells, respectively. ICG-dasatinib accumulated in subcutaneous xenografts in mice. Fluorescent signals were also observed in liver and gallbladder, indicating biliary excretion; however, fluorescence intensity of tumors was significantly higher than that of intestine after washing. Strong fluorescent signals were observed in orthotopic xenografts through the covering normal mucosa in rats. Indocyanine green-labeled dasatinib could visualize GIST cells and xenografted tumors. The antitumor effect of ICG-dasatinib was preserved to the same degree as imatinib. (Link to Publication Site) ● Publication site (DOI): 10.1111/jgh.15281 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 32989784 ● Search Scopus @ Elsevier (PMID): 32989784 ● Search Scopus @ Elsevier (DOI): 10.1111/jgh.15281 (DOI: 10.1111/jgh.15281, PubMed: 32989784)
11.	Michiyasu Nakao, Munehisa Toguchi, Yuki Shimabukuro and Shigeki Sano : Tandem Thia-Michael/Dieckmann Condensation of Allenyl Esters for the Regioselective Synthesis of Trisubstituted Thiophenes, Tetrahedron Letters, Vol.61, No.36, 152271, 2020. (Summary) Tandem thia-Michael/Dieckmann condensation of allenyl esters with methyl mercaptoacetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded 2,3,5-trisubstituted thiophenes regioselectively. On the other hand, 2,3,4-trisubstituted thiophenes were obtained as the sole product by tandem thia- Michael/Dieckmann condensation employing magnesium bromide and triethylamine. (Keyword) Thia-Michael/Dieckmann condensation / Trisubstituted thiophene / Allenyl ester / Methyl mercaptoacetate / Magnesium bromide (Tokushima University Institutional Repository) ● Metadata: 115121 (Link to Publication Site) ● Publication site (DOI): 10.1016/j.tetlet.2020.152271 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1016/j.tetlet.2020.152271 (Tokushima University Institutional Repository: 115121, DOI: 10.1016/j.tetlet.2020.152271)
12.	Michiyasu Nakao, Ayumu Adachi, Syuji Kitaike and Shigeki Sano : Synthesis of Three Stereoisomers of Erythrochelin, a Hydroxamate-Type Tetrapeptide Siderophore from Saccharopolyspora erythraea, Heterocycles, Vol.101, No.1, 347-356, 2020. (Summary) Details of the synthesis of three stereoisomers of erythrochelin, a hydroxamate-type tetrapeptide siderophore produced by Saccharopolyspora erythraea, were described. Both enantiomers of protected δ-N-hydroxyornithine were used as key intermediates in the synthesis of stereoisomers of erythrochelin containing a (3S,6S)-3,6-disubstituted-2,5-diketopiperazine ring. From comparisons of 1H and 13C NMR spectra, neither of stereoisomers provided a match for the erythrochelin spectral data, and the absolute configuration of erythrochelin was unambiguously reconfirmed to be (R,R,S,S). (Keyword) erythrochelin / siderophore / absolute configuration / 2,5-diketopiperazine / δ-N-hydroxyornithine (Tokushima University Institutional Repository) ● Metadata: 114107 (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-19-S(F)27 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.3987/COM-19-S(F)27 (Tokushima University Institutional Repository: 114107, DOI: 10.3987/COM-19-S(F)27)
13.	Shigeki Sano, Tomoya Matsumoto, Munehisa Toguchi and Michiyasu Nakao : Facile Two-Step Synthesis of Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate by Exploiting GareggSamuelsson Reaction Conditions, Synlett, Vol.29, No.11, 1461-1464, 2018. (Keyword) HornerWadsworthEmmons reagents / StillGennari reagent / phosphorus / GareggSamuelsson reaction conditions / 2,2,2-trifluoroethanol (Tokushima University Institutional Repository) ● Metadata: 113942 (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0036-1591566 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0036-1591566 (Tokushima University Institutional Repository: 113942, DOI: 10.1055/s-0036-1591566)
14.	Michiyasu Nakao, Nanako Nishikiori, Akihito Nakamura, Murasaki Miyagi, Nao Shibata, Syuji Kitaike, Makoto Fukui, Hiro-O Ito and Shigeki Sano : Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde, SynOpen, Vol.2, No.1, 50-57, 2018. (Summary) o-Phthalaldehyde (OPA) reacts with O-protected tris(hydroxyalkyl)aminomethanes in the presence of 1-propanethiol to afford a novel class of stable isoindoles. Steric protection provided by the bulkiness of C 3-symmetric primary amines derived from tris(hydroxymethyl)aminomethane could be significant for the stabilization of 1-alkylthio-2-alkyl-substituted isoindoles derived from OPA. A plausible reaction mechanism is proposed to explain the formation of the isoindole and an isoindolin-1-one by-product. (Keyword) o-phthalaldehyde / isoindole / steric protection / isoindolin-1-one (Tokushima University Institutional Repository) ● Metadata: 113941 (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0036-1591932 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0036-1591932 (Tokushima University Institutional Repository: 113941, DOI: 10.1055/s-0036-1591932)
15.	Shiroh Fujii, Shingen Nakamura, Asuka Oda, Hirokazu Miki, Hirofumi Tenshin, Jumpei Teramachi, Masahiro Hiasa, Ariunzaya Bat-Erdene, Yusaku Maeda, Masahiro Oura, Mamiko Takahashi, Masami Iwasa, Itsuro Endo, Sumiko Yoshida, Ken-ichi Aihara, Kiyoe Kurahashi, Takeshi Harada, Kumiko Kagawa, Michiyasu Nakao, Shigeki Sano and Masahiro Abe : Unique anti-myeloma activity by thiazolidine-2,4-dione compounds with Pim inhibiting activity., British Journal of Haematology, Vol.180, No.2, 246-258, 2018. (Summary) Proviral Integrations of Moloney virus 2 (PIM2) is overexpressed in multiple myeloma (MM) cells, and regarded as an important therapeutic target. Here, we aimed to validate the therapeutic efficacy of different types of PIM inhibitors against MM cells for their possible clinical application. Intriguingly, the thiazolidine-2,4-dione-family compounds SMI-16a and SMI-4a reduced PIM2 protein levels and impaired MM cell survival preferentially in acidic conditions, in contrast to other types of PIM inhibitors, including AZD1208, CX-6258 and PIM447. SMI-16a also suppressed the drug efflux function of breast cancer resistance protein, minimized the sizes of side populations and reduced in vitro colony-forming capacity and in vivo tumourigenic activity in MM cells, suggesting impairment of their clonogenic capacity. PIM2 is known to be subject to ubiquitination-independent proteasomal degradation. Consistent with this, the proteasome inhibitors bortezomib and carfilzomib increased PIM2 protein levels in MM cells without affecting its mRNA levels. However, SMI-16a mitigated the PIM2 protein increase and cooperatively enhanced anti-MM effects in combination with carfilzomib. Collectively, the thiazolidine-2,4-dione-family compounds SMI-16a and SMI-4a uniquely reduce PIM2 protein in MM cells, which may contribute to their profound efficacy in addition to their immediate kinase inhibition. Their combination with proteasome inhibitors is envisioned. (Keyword) Animals / Antineoplastic Agents / Cell Line, Tumor / Cell Survival / Cell Transformation, Neoplastic / Disease Models, Animal / Humans / Hydrogen-Ion Concentration / Mice / Multiple Myeloma / Proteasome Inhibitors / Protein-Serine-Threonine Kinases / Proteolysis / Proto-Oncogene Proteins / Thiazolidinediones (Tokushima University Institutional Repository) ● Metadata: 112752 (Link to Publication Site) ● Publication site (DOI): 10.1111/bjh.15033 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 29327347 ● Summary page in Scopus @ Elsevier: 2-s2.0-85040344893 (Tokushima University Institutional Repository: 112752, DOI: 10.1111/bjh.15033, PubMed: 29327347, Elsevier: Scopus)
16.	Michiyasu Nakao, Kazue Tanaka, Syuji Kitaike and Shigeki Sano : Synthesis of Fluorine-Containing Analogues of 1-Lysoglycerophospholipids via HornerWadsworthEmmons Reaction, Synthesis, Vol.49, No.16, 3654-3661, 2017. (Summary) An efficient method of synthesizing fluorine-containing analogues of 1-lysoglycerophospholipids (1-LPLs) by introducing a palmitoyl moiety starting from bis(2,2,2-trifluoroethyl)phosphonoacetate (StillGennari reagent) is described. The method effectively employs HornerWadsworthEmmons reagents as masked 1-LPL derivatives to prepare a series of analogues of 1-lysophosphatidic acid (1-LPA), 1-lysophosphatidylethanolamine (1-LPE), and 1-lysophosphatidylcholine (1-LPC). (Keyword) lysoglycerophospholipid / HornerWadsworthEmmons reaction / fluorine / lysophosphatidic acid / lysophosphatidylethanolamine / lysophosphatidylcholine (Tokushima University Institutional Repository) ● Metadata: 113940 (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0036-1588826 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0036-1588826 (Tokushima University Institutional Repository: 113940, DOI: 10.1055/s-0036-1588826)
17.	Natsumi Fujiwara, Keiji Murakami, Michiyasu Nakao, Munehisa Toguchi, Hiromichi Yumoto, Katsuhiko Hirota, Takashi Matsuo, Shigeki Sano, Kazumi Ozaki and Yoichiro Miyake : Antibacterial and antibiofilm effects of Reuterin-Related Compounds to periodontopathic bacteria, Journal of Oral Health and Biosciences, Vol.30, No.1, 8-17, 2017. (Tokushima University Institutional Repository) ● Metadata: 111063 (Link to Publication Site) ● Publication site (DOI): 10.20738/johb.30.1_8 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.20738/johb.30.1_8 (Tokushima University Institutional Repository: 111063, DOI: 10.20738/johb.30.1_8)
18.	Natsumi Fujiwara, Keiji Murakami, Michiyasu Nakao, Munehisa Toguchi, Hiromichi Yumoto, Takashi Amoh, Katsuhiko Hirota, Takashi Matsuo, Shigeki Sano, Kazumi Ozaki and Yoichiro Miyake : Novel reuterin-related compounds suppress odour by periodontopathic bacteria, Oral Diseases, Vol.23, No.4, 492-497, 2017. (Summary) Halitosis is caused by volatile sulphur compounds including methyl mercaptan (CH3 SH) in the oral cavity and is a serious problem that limits interpersonal social communication. The aim of study was to evaluate the effects of reuterin-related compounds (RRCs) on halitosis-related periodontopathic bacteria in vitro. RRC-01, RRC-02 and RRC-03 (32 and 64 g ml(-1) ) in culture media containing Fusobacterium nucleatum JCM8523 and Porphyromonas gingivalis ATCC33277 were used. The effects of RRCs on CH3 SH production and detectable odour by F. nucleatum and P. gingivalis were examined by CH3 SH production assay and organoleptic test, respectively. The number of bacterial cells was also measured using an ATP assay. In P. gingivalis treated with RRCs, the expression of mgl gene, which is responsible for CH3 SH production, was examined by qRT-PCR. CH3 SH production and the score of detectable odour from F. nucleatum and P. gingivalis culture media containing RRCs were significantly lower than that without RRCs (P < 0.05). The expression of mgl gene in P. gingivalis was significantly downregulated by RRC-01 (P < 0.01), but not by RRC-02 or RRC-03. RRCs are potent oral care products for preventing halitosis via reducing CH3 SH production. (Link to Publication Site) ● Publication site (DOI): 10.1111/odi.12638 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 28083982 ● Summary page in Scopus @ Elsevier: 2-s2.0-85015084211 (DOI: 10.1111/odi.12638, PubMed: 28083982, Elsevier: Scopus)
19.	Shigeki Sano, Eiko Kujime, Hiroko Tanaka, Syuji Kitaike and Michiyasu Nakao : Enzymatic Synthesis of Chiral P-Stereogenic Phosphonoacetates, Chemical Data Collections, Vol.5/6, 12-20, 2016. (Summary) In this data article, we describe the enzymatic kinetic resolution of a series of racemic mixed phosphonoacetates, which were successfully prepared from methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent) by alcoholysis with -symmetrical secondary alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Porcine liver esterase (PLE)-catalyzed kinetic resolution of some of these racemic mixed phosphonoacetates proceeded in a highly stereoselective manner to furnish the chiral P-stereogenic phosphonoacetates (up to > 99% ee). (Keyword) stereogenic phosphorus atom / methyl bis(2,2,2-trifluoroethyl)phosphonoacetate / Horner-Wadsworth-Emmons reagent / kinetic resolution / enzymatic hydrolysis / X-ray crystal structure (Tokushima University Institutional Repository) ● Metadata: 113939 (Link to Publication Site) ● Publication site (DOI): 10.1016/j.cdc.2016.09.001 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1016/j.cdc.2016.09.001 (Tokushima University Institutional Repository: 113939, DOI: 10.1016/j.cdc.2016.09.001)
20.	Michiyasu Nakao, Shunsuke Tsuji, Syuji Kitaike and Shigeki Sano : Synthesis of Erythrochelin: A Hydroxamate-Type Siderophore from Saccharopolyspora erythraea, Synthesis, Vol.48, No.23, 4149-4154, 2016. (Summary) Erythrochelin, a hydroxamate-type siderophore produced by Saccharopolyspora erythraea, is synthesized for the first time. A key building block of erythrochelin containing the 2,5-diketopiperazine ring is prepared by intramolecular cyclization of the corresponding dipep- tide precursor derived from two kinds of protected -N-hydroxy-L-orni- thines. Consecutive condensation of the building block with protected D-serine and protected -N-hydroxy-D-ornithine, followed by deprotec- tion, furnishes erythrochelin. (Keyword) erythrochelin / rhodotorulic acid / siderophore / 2,5-diketo- piperazine / electrospray ionization mass spectrometry (Tokushima University Institutional Repository) ● Metadata: 113938 (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0035-1560564 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0035-1560564 (Tokushima University Institutional Repository: 113938, DOI: 10.1055/s-0035-1560564)
21.	Michiyasu Nakao, Yuta Hiroyama, Shintaro Fukayama and Shigeki Sano : N4-Methylation Changes the Conformation of (3S,6S)-3-Alkyl-6-benzylpiperazine-2,5-diones from Folded to Extended, Journal of Molecular Structure, Vol.1116, 37-44, 2016. (Summary) N4-Methylation of (3S,6S)-3-alkyl-6-benzylpiperazine-2,5-diones (S,S)-1ac was found to change their folded conformation to an extended conformation. Conformational aspects of N1- and/or N4-methylated (S,S)-1ac were revealed by single crystal X-ray crystallography and 1H NMR spectroscopy. (Keyword) piperazine-2,5-dione / N-methylation / folded conformation / extended conformation / CH/ interaction / X-ray crystal structure (Tokushima University Institutional Repository) ● Metadata: 113937 (Link to Publication Site) ● Publication site (DOI): 10.1016/j.molstruc.2016.03.019 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1016/j.molstruc.2016.03.019 (Tokushima University Institutional Repository: 113937, DOI: 10.1016/j.molstruc.2016.03.019)
22.	Shigeki Sano, Masanori Kamura, Akihito Nakamura, Syuji Kitaike and Michiyasu Nakao : Asymmetric Synthesis of cis-4a,5,8,8a-Tetrahydrophthalazin-1(2H)-one Derivatives Based on Organocatalytic Alcoholysis of Cyclic Dicarboxylic Anhydride, Heterocycles, Vol.93, No.1, 391-398, 2016. (Summary) Asymmetric synthesis of optically active cis-4-phenyl-4a,5,8,8a- tetrahydrophthalazin-1(2H)-one and its N-alkylated derivatives based on an organocatalytic enantioselective alcoholysis of cyclic dicarboxylic anhydride was described. (Keyword) cis-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one / organocatalysts / enantioselective alcoholysis / chiral sulfonamide / phosphodiesterase type 4 (Tokushima University Institutional Repository) ● Metadata: 113936 (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-15-S(T)17 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.3987/COM-15-S(T)17 (Tokushima University Institutional Repository: 113936, DOI: 10.3987/COM-15-S(T)17)
23.	Ryouhei Yamashita, Yumika Tabata, Erina Iga, Michiyasu Nakao, Shigeki Sano, Kentaro Kogure, Akira Tokumura and Tamotsu Tanaka : Analysis of molecular species profiles of ceramide-1-phosphate and sphingomyelin using MALDI-TOF mass spectrometry, Lipids, Vol.51, No.2, 263-270, 2016. (Summary) Ceramide-1-phosphate (C1P) is a potential signaling molecule that modulates various cellular functions in animals. It has been known that C1P with different N-acyl lengths induce biological responses differently. However, molecular species profiles of the C1P in animal tissues have not been extensively examined yet. Here, we developed a method for determination of the molecular species of a C1P using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry with Phos-tag, a phosphate capture molecule. The amounts of total C1P in skin, brain, liver, kidney and small intestine of mice were determined to be 344, 151, 198, 96 and 90 pmol/g wet weight, respectively. We found a C1P species having an α-hydroxypalmitoyl residue (h-C1P, 44 pmol/g wet weight) in mouse skin. The h-C1P was detected only in the skin, and not other tissues of mice. The same analysis was applied to sphingomyelin after conversion of sphingomyelin to C1P by Streptomyces chromofuscus phospholipase D. We found that molecular species profiles of sphingomyelin in skin, kidney and small intestine of mice were similar to those of C1P in corresponding tissues. In contrast, molecular species profiles of sphingomyelin in liver and brain were quite different from those of C1P in these tissues, indicating selective synthesis or degradation of C1P in these tissues. The method described here will be useful for detection of changes in molecular species profiles of C1P and sphingomyelin. (Link to Publication Site) ● Publication site (DOI): 10.1007/s11745-015-4082-0 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 26694604 ● Summary page in Scopus @ Elsevier: 2-s2.0-84957439211 (DOI: 10.1007/s11745-015-4082-0, PubMed: 26694604, Elsevier: Scopus)
24.	Shigeki Sano, Tomoya Matsumoto, Teppei Yano, Munehisa Toguchi and Michiyasu Nakao : Synthesis of Allenyl Esters by Horner-Wadsworth-Emmons Reactions of Ketenes Mediated by Isopropylmagnesium Bromide, Synlett, Vol.26, No.15, 2135-2138, 2015. (Tokushima University Institutional Repository) ● Metadata: 114094 (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0034-1378803 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0034-1378803 (Tokushima University Institutional Repository: 114094, DOI: 10.1055/s-0034-1378803)
25.	Shigeki Sano, Hayato Sumiyoshi, Atsuhi Handa, Rie Tokizane and Michiyasu Nakao : A Novel Synthetic Approach to Glycerophospholipid via Horner-Wadsworth-Emmons Reaction of Mixed Phosphonoacetate, Tetrahedron Letters, Vol.56, No.32, 4686-4688, 2015. (Summary) A novel synthetic approach to glycerophospholipids featuring the use of Horner-Wadsworth-Emmons reagents as masked glycerophospholipids has been developed. Based on the method, phosphatidic acid (PA), phosphatidylethanolamine (PE), and phosphatidylcholine (PC) containing palmitoyl moieties were readily synthesized from a mixed phosphonoacetate as a common key intermediate. (Keyword) Glycerophospholipid / Horner-Wadsworth-Emmons reaction / Phosphatidic acid / Phosphatidylethanolamine / Phosphatidylcholine (Link to Publication Site) ● Publication site (DOI): 10.1016/j.tetlet.2015.06.033 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-84938208564 (DOI: 10.1016/j.tetlet.2015.06.033, Elsevier: Scopus)
26.	Michiyasu Nakao, Shintaro Fukayama, Syuji Kitaike and Shigeki Sano : Synthesis of Rhodotorulic Acid and Its 1,4-Dimethylated Derivative, Heterocycles, Vol.90, No.2, 1309-1316, 2015. (Keyword) rhodotorulic acid / diketopiperazine / siderophore / microwave irradiation / N-hydroxyacetamide (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-14-S(K)67 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1520854805248223232 ● Summary page in Scopus @ Elsevier: 2-s2.0-84923241589 (DOI: 10.3987/COM-14-S(K)67, CiNii: 1520854805248223232, Elsevier: Scopus)
27.	Shigeki Sano, Tomoya Matsumoto, Hiroshi Nanataki, Shota Tempaku and Michiyasu Nakao : Z-Selective HornerWadsworthEmmons Reaction of 2-TOM-cyclopentanone for the Synthesis of rac-N-Cbz-Gly-[(Z)-CF=C]-Pro-OH Dipeptide Isostere, Tetrahedron Letters, Vol.55, No.45, 6248-6251, 2014. (Keyword) Horner-Wadsworth-Emmons reaction / Fluoroolefin / Proline / Grignard reagent / Z-selective (Link to Publication Site) ● Publication site (DOI): 10.1016/j.tetlet.2014.09.077 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-84908236883 (DOI: 10.1016/j.tetlet.2014.09.077, Elsevier: Scopus)
28.	Shigeki Sano, Tomoya Matsumoto and Michiyasu Nakao : E-Selective Horner-Wadsworth-Emmons Reaction of 2-OBO-cyclopentanone for the Synthesis of rac-N-Cbz-Gly-[(E)-CF=C]-Pro-OH Dipeptide Isostere, Tetrahedron Letters, Vol.55, No.32, 4480-4483, 2014. (Keyword) Horner-Wadsworth-Emmons reaction / Fluoroolefin / Proline / OBO ester / E-selective (Link to Publication Site) ● Publication site (DOI): 10.1016/j.tetlet.2014.06.063 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1016/j.tetlet.2014.06.063 (DOI: 10.1016/j.tetlet.2014.06.063)
29.	Masahiro Hiasa, Jumpei Teramachi, A Oda, Ryota Amachi, T Harada, Shingen Nakamura, Hirokazu Miki, Shiroh Fujii, Kumiko Kagawa, Keiichiro Watanabe, Itsuro Endo, Y Kuroda, T Yoneda, Daisuke Tsuji, Michiyasu Nakao, Eiji Tanaka, Kenichi Hamada, Shigeki Sano, Kouji Itou, Toshio Matsumoto and Masahiro Abe : Pim-2 kinase is an important target of treatment for tumor progression and bone loss in myeloma., Leukemia, 2014. (Summary) Pim-2 kinase is overexpressed in multiple myeloma (MM) cells to enhance their growth and survival, and regarded as a novel therapeutic target in MM. However, the impact of Pim-2 inhibition on bone disease in MM remains unknown. We demonstrated here that Pim-2 expression was also upregulated in bone marrow stromal cells and MC3T3-E1 preosteoblastic cells in the presence of cytokines known as the inhibitors of osteoblastogenesis in MM, including interleukin-3 (IL-3), IL-7, tumor necrosis factor-, transforming growth factor- (TGF-) and activin A, as well as MM cell conditioned media. The enforced expression of Pim-2 abrogated in vitro osteoblastogenesis by BMP-2, which suggested Pim-2 as a negative regulator for osteoblastogenesis. Treatment with Pim-2 short-interference RNA as well as the Pim inhibitor SMI-16a successfully restored osteoblastogenesis suppressed by all the above inhibitory factors and MM cells. The SMI-16a treatment potentiated BMP-2-mediated anabolic signaling while suppressing TGF- signaling. Furthermore, treatment with the newly synthesized thiazolidine-2,4-dione congener, 12a-OH, as well as its prototypic SMI-16a effectively prevented bone destruction while suppressing MM tumor growth in MM animal models. Thus, Pim-2 may have a pivotal role in tumor progression and bone loss in MM, and Pim-2 inhibition may become an important therapeutic strategy to target the MM cell-bone marrow interaction.Leukemia advance online publication, 30 May 2014; doi:10.1038/leu.2014.147. (Link to Publication Site) ● Publication site (DOI): 10.1038/leu.2014.147 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 24787487 ● Search Scopus @ Elsevier (PMID): 24787487 ● Search Scopus @ Elsevier (DOI): 10.1038/leu.2014.147 (DOI: 10.1038/leu.2014.147, PubMed: 24787487)
30.	Michiyasu Nakao, Yuriko Toriuchi, Shintaro Fukayama and Shigeki Sano : Synthesis and Conformational Characterization of Diketopiperazines Bearing a Benzyl Moiety, Chemistry Letters, Vol.43, No.3, 340-352, 2014. (Summary) Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1H NMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1H NMR spectra. An intramolecular CH- interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group. (Link to Publication Site) ● Publication site (DOI): 10.1246/cl.131001 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1390001204587532928 ● Summary page in Scopus @ Elsevier: 2-s2.0-84897714589 (DOI: 10.1246/cl.131001, CiNii: 1390001204587532928, Elsevier: Scopus)
31.	Shigeki Sano, Keisuke Matsuura, Hayato Sumiyoshi, Akira Miki, Syuji Kitaike and Michiyasu Nakao : Reinvestigation of 1,3,4-Thiadiazol-2(3H)-Iminium Bromide in the Two-Step Synthesis of Imdazo[2,1-b][1,3,4]-Thiadiazoles, Heterocycles, Vol.89, No.4, 1041-1053, 2014. (Keyword) 1,3,4-thiadiazol-2(3H)-iminium bromide / imidazo[2,1-b][1,3,4]thiadiazole / thiadiazole / imidazole / microwave irradiation (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-14-12938 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-84897532461 (DOI: 10.3987/COM-14-12938, Elsevier: Scopus)
32.	Shigeki Sano, Takeshi Tsumura, Masashi Horibe and Michiyasu Nakao : Catalytic Asymmetric Ring-Opening of -Symmetric Cyclic Carbonates with Chiral Brønsted Acid Catalysts, Synlett, Vol.24, No.17, 2302-2304, 2013. (Keyword) asymmetric synthesis (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0033-1339845 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0033-1339845 (DOI: 10.1055/s-0033-1339845)
33.	Shigeki Sano, Takashi Ichikawa, Michiyasu Nakao and Yoshimitsu Nagao : Deconjugative Esterification of 2-(4-Phenylcyclohexylidne)acetic Acid via Intramolecular Chirality Transfer, Chemistry Letters, Vol.41, No.2, 189-190, 2012. (Link to Publication Site) ● Publication site (DOI): 10.1246/cl.2012.189 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1360846644041797248 ● Search Scopus @ Elsevier (DOI): 10.1246/cl.2012.189 (DOI: 10.1246/cl.2012.189, CiNii: 1360846644041797248)
34.	Shigeki Sano, Takashi Ichikawa, Michiyasu Nakao and Yoshimitsu Nagao : A Microwave-Assisted Deconjugative Esterification of α,β-Unsaturated Carboxylic Acids through alpha,beta-Unsaturated Ketene Intermediates, Chemistry Letters, Vol.41, No.1, 68-69, 2012. (Link to Publication Site) ● Publication site (DOI): 10.1246/cl.2012.68 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1246/cl.2012.68 (DOI: 10.1246/cl.2012.68)
35.	Shigeki Sano, Yoshinori Okubo, Atsushi Handa, Michiyasu Nakao, Syuji Kitaike, Yoshimitsu Nagao and Hisao Kakegawa : Reinvestigation of the Synthesis of Isoliquiritigenin (ILG): Application of Horner-Wadsworth-Emmons Reaction and Claisen-Schmidt Condensation, Chemical & Pharmaceutical Bulletin, Vol.59, No.7, 885-888, 2011. (Summary) Isoliquiritigenin [ILG, (E)-1] was readily prepared via the Horner-Wadsworth-Emmons reactions using β-ketophosphonates 5a, b. An improved protocol for the synthesis of (E)-1 via the Claisen-Schmidt condensation was also presented. (Keyword) isoliquiritigenin / chalcone / Horner-Wadsworth-Emmons reaction / Claisen-Schmidt condensation / cis-trans isomerization (Link to Publication Site) ● Publication site (DOI): 10.1248/cpb.59.885 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 21720042 ● Search Scopus @ Elsevier (PMID): 21720042 ● Search Scopus @ Elsevier (DOI): 10.1248/cpb.59.885 (DOI: 10.1248/cpb.59.885, PubMed: 21720042)
36.	Kaori Ueda, Masanori Yoshihara, Michiyasu Nakao, Tamotsu Tanaka, Shigeki Sano, Kenji Fukuzawa and Akira Tokumura : Evaluation of inhibitory actions of flavonols and related substances on lysophospholipase d activity of serum autotaxin by a convenient assay using a chromogenic substrate., Journal of Agricultural and Food Chemistry, Vol.58, No.10, 6053-6063, 2010. (Summary) Overproduction of lysophosphatidic acid (LPA) by lysophospholipase D/autotaxin (lysoPLD/ATX) is postulated to be involved in the promotion of cancer and atherosclerosis. A lysoPLD inhibitor may be utilized to ameliorate the LPA-related pathological conditions. In this study, a new assay was devised to quantify p-nitrophenol from hydrolysis of chromogenic substrate by serum lysoPLD without tedious lipid extraction procedures. Flavonols, phenolic acids, free fatty acids, and N-acyltyrosines inhibited lysoPLD activity in a micromolar range. They were classified into competitive, noncompetitive, or mixed type inhibitors. The results show that the low hydrophobicity of an inhibitor is a critical factor in its preference for the binding to a noncatalytic binding site over a catalytic binding site. Considering its reported bioavailability and the low dependency of its inhibitory activity on serum dilution, flavonol is likely to be a more effective lysoPLD inhibitor in human blood circulation in vivo than the other inhibitors including LPA. (Keyword) Binding Sites / Binding, Competitive / Enzyme Inhibitors / Flavonols / Humans / Multienzyme Complexes / Phosphodiesterase I / Phosphoric Diester Hydrolases / Pyrophosphatases / Recombinant Proteins (Link to Publication Site) ● Publication site (DOI): 10.1021/jf904155a (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 20415488 ● Search Scopus @ Elsevier (PMID): 20415488 ● Search Scopus @ Elsevier (DOI): 10.1021/jf904155a (DOI: 10.1021/jf904155a, PubMed: 20415488)
37.	Shigeki Sano, Takeshi Tsumura, Noriaki Tanimoto, Takashi Honjo, Michiyasu Nakao and Yoshimitsu Nagao : Modified Cinchona Alkaloid-Zinc Complex Catalysts: Enantioselective Monoacetylation of Glycerol Derivatives with Acetic Anhydride, Synlett, No.2, 256-260, 2010. (Keyword) cinchona alkaloid / zinc complex / asymmetric synthesis / glycerol / acetylation (Link to Publication Site) ● Publication site (DOI): 10.1055/s-0029-1218562 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.1055/s-0029-1218562 (DOI: 10.1055/s-0029-1218562)
38.	Shigeki Sano, Michiyasu Nakao, Masanori Takeyasu, Syuji Kitaike, Yasuko Yoshioka and Yoshimitsu Nagao : Use of Diketopiperazines for Determining Absolute Configurations of α-Substituted Serines by ¹H-NMR Spectroscopy, Heterocycles, Vol.79, No.1, 781-789, 2009. (Keyword) Diketopiperazine / Absolute Configuration / α-SubstitutedSerine / 1H-NMR Analysis / DKP Method (Link to Publication Site) ● Publication site (DOI): 10.3987/COM-08-S(D)47 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1520010379846386176 ● Search Scopus @ Elsevier (DOI): 10.3987/COM-08-S(D)47 (DOI: 10.3987/COM-08-S(D)47, CiNii: 1520010379846386176)
39.	Kazuyuki Kuwayama, Kazuhito Matsuzaki, Yoshifumi Mizobuchi, Hideo Mure, Keiko T. Kitazato, Teruyoshi Kageji, Michiyasu Nakao and Shinji Nagahiro : Promyelocytic leukemia protein induces apoptosis due to caspase-8 activation via the repression of NFkB activation in glioblastoma, Neuro-Oncology, Vol.11, No.2, 132-141, 2009. (Summary) Promyelocytic leukemia (PML) protein plays an essential role in the induction of apoptosis; its expression is reduced in various cancers. As the functional roles of PML in glioblastoma multiforme (GBM) have not been clarified, we assessed the expression of PML protein in GBM tissues and explored the mechanisms of PML-regulated cell death in GBM cells. We examined the PML mRNA level and the expression of PML protein in surgical GBM specimens. PML-regulated apoptotic mechanisms in GBM cells transfected with plasmids expressing the PML gene were examined. The protein expression of PML was significantly lower in GBM than in non-neoplastic tissues; approximately 10% of GBM tissues were PML-null. The PML mRNA levels were similar in both tissue types. The overexpression of PML activated caspase-8 and induced apoptosis in GBM cells. In these cells, PML decreased the expression of transactivated forms of NFkappaB/p65, and c-FLIP gene expression was suppressed. Therefore, PML-induced apoptosis resulted from the suppression of the transcriptional activity of NFkappaB/p65. PML overexpression decreased phosphorylated IkappaBalpha and nuclear NFkappaB/p65 and increased the expression of the suppressor of cytokine signaling (SOCS-1). A proteasome inhibitor blocked the reduction of activated p65 by PML. The reduction of PML is associated with the pathogenesis of GBM. PML induces caspase-8-dependent apoptosis via the repression of NFkappaB activation by which PML facilitates the proteasomal degradation of activated p65 and the sequestration of p65 with IkappaBalpha in the cytoplasm. This novel mechanism of PML-regulated apoptosis may represent a therapeutic target for GBM. (Keyword) apoptosis caspase, glioblastoma, NFkB/p65, promyelocytic leukemia (Link to Publication Site) ● Publication site (DOI): 10.1215/15228517-2008-083 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 18812519 ● Search Scopus @ Elsevier (PMID): 18812519 ● Search Scopus @ Elsevier (DOI): 10.1215/15228517-2008-083 (DOI: 10.1215/15228517-2008-083, PubMed: 18812519)
40.	Shigeki Sano, Michiyasu Nakao, Masanori Takeyasu, Chiyo Yamamoto, Syuji Kitaike, Yasuko Yoshioka and Yoshimitsu Nagao : Chemoenzymatic Synthesis of α-Substituted Serines via Enantiodivergent Transformation, The Open Organic Chemistry Journal, Vol.3, 22-34, 2009. (Link to Publication Site) ● Publication site (DOI): 10.2174/1874095200903010022 (Link to Search Site for Scientific Articles) ● Search Scopus @ Elsevier (DOI): 10.2174/1874095200903010022 (DOI: 10.2174/1874095200903010022)
41.	Takashi Honjo, Michiyasu Nakao, Shigeki Sano, Motoo Shiro, Kentaro Yamaguchi, Yoshihisa Sei and Yoshimitsu Nagao : Nonenzymatic Enantioselective Monoacetylation of Prochiral 2-Protectedamino-2-alkyl-1,3-propanediols Utilizing a Chiral Sulfonamide-Zn Complex Catalyst, Organic Letters, Vol.9, No.3, 509-512, 2007. (Summary) [structure: see text] Treatment of a chiral sulfonamide with Et(2)Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral N-Boc-2-amino-2-alkyl-1,3-propanediols with Ac(2)O in the presence of 5 mol % of chiral sulfonamide-Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70-92% yields with 70-88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis. (Keyword) Acetylation / Alkylation / Amines / Catalysis / Models, Chemical / Models, Molecular / Organometallic Compounds / Propylene Glycols / Stereoisomerism / Sulfonamides / zinc (Link to Publication Site) ● Publication site (DOI): 10.1021/ol063063g (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 17249799 ● Search Scopus @ Elsevier (PMID): 17249799 ● Search Scopus @ Elsevier (DOI): 10.1021/ol063063g (DOI: 10.1021/ol063063g, PubMed: 17249799)
42.	Shigeki Sano, Etsuko Harada, Tomohiro Azetsu, Takashi Ichikawa, Michiyasu Nakao and Yoshimitsu Nagao : Novel Deconjugative Esterification of 2-Cyclohexylidneacetic Acids through 4-(Pyrrolidin-1-yl)pyridine Catalyzed Carbodiimide Couplings, Chemistry Letters, Vol.35, No.11, 1286-1287, 2006. (Link to Publication Site) ● Publication site (DOI): 10.1246/cl.2006.1286 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1360846644040903936 ● Search Scopus @ Elsevier (DOI): 10.1246/cl.2006.1286 (DOI: 10.1246/cl.2006.1286, CiNii: 1360846644040903936)
43.	Shigeki Sano, Shinobu Abe, Tomohiro Azetsu, Michiyasu Nakao, Motoo Shiro and Yoshimitsu Nagao : Diastereoselective Horner-Wadsworth-Emmons Reaction for the Synthesis of Tetrasubstituted Alkenes with an Axis of Chirality, Letters in Organic Chemistry, Vol.3, No.11, 798-801, 2006. (Link to Publication Site) ● Publication site (DOI): 10.2174/157017806779116969 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-33845868763 (DOI: 10.2174/157017806779116969, Elsevier: Scopus)
44.	Shigeki Sano, Michiyasu Nakao, Masanori Takeyasu, Takashi Honjo and Yoshimitsu Nagao : Lipase-catalyzed Enantioselective Acetylation of Prochiral N-Cbz-2-Alkyl-2-amino-1,3-propanediols and Enantiodivergent Synthesis of α-Benzylserine, Letters in Organic Chemistry, Vol.3, No.10, 764-767, 2006. (Link to Publication Site) ● Publication site (DOI): 10.2174/157017806779025924 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-33845645390 (DOI: 10.2174/157017806779025924, Elsevier: Scopus)

Review, Commentary:

1.	Naoki Muguruma, 藤本将太, 樫原孝典, 三橋威志, 宮本佳彦, Koichi Okamoto, Michiyasu Nakao, Shigeki Sano and Tetsuji Takayama : Recent Advances in Endoscopic Molecular Imaging of Gastrointestinal Cancer, OPTRONICS, Vol.39, No.9, 117-121, Sep. 2020. (Tokushima University Institutional Repository) ● Metadata: 115746 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1050005888433240576 (Tokushima University Institutional Repository: 115746, CiNii: 1050005888433240576)
2.	Michiyasu Nakao : 新しいホスホノアミダート型プロドラッグの開発, Farumashia, Vol.55, No.6, 569, Jun. 2019. (Keyword) ホスホノアミダート / プロドラッグ / Vγ9 Vδ2 T細胞 / ブチロフィリン3A1 (Tokushima University Institutional Repository) ● Metadata: 115329 (Link to Publication Site) ● Publication site (DOI): 10.14894/faruawpsj.55.6_569 (Link to Search Site for Scientific Articles) ● CiNii @ National Institute of Informatics (CRID): 1390564238097269120 ● Search Scopus @ Elsevier (DOI): 10.14894/faruawpsj.55.6_569 (Tokushima University Institutional Repository: 115329, DOI: 10.14894/faruawpsj.55.6_569, CiNii: 1390564238097269120)
3.	Michiyasu Nakao : Development of Novel Functional Molecules Based on the Molecular Structure Characteristics of Diketopiperazines, Journal of the Pharmaceutical Society of Japan, Vol.137, No.12, 1505-1516, Dec. 2017. (Summary) This article focuses on our investigation of the molecular structure characteristics of diketopiperazines (DKPs), and application of these findings to the development of novel functional molecules. DKPs bearing a benzyl moiety are known to adopt a folded conformation, in which the benzyl moiety is folded over the DKP ring. In order to investigate the driving force behind the folded conformation, we synthesized DKPs bearing a benzyl moiety with different para-substituents, and demonstrated that the folded conformation likely arose from intramolecular CH/ϖ interactions, based on the electronic effects of para-substituents on the benzyl group in H NMR spectroscopy. On the other hand, N4-methylation of DKPs bearing a benzyl moiety was found to change their folded conformation to an extended conformation, based on single crystal X-ray crystallography and H NMR spectroscopy analysis. Next, we attempted to synthesize both hydroxamate-type siderophores containing the DKP ring: rhodotorulic acid and erythrochelin. Facile synthesis of rhodotorulic acid and its N,N'-dimethylated derivative was achieved by microwave-assisted cyclization of the corresponding dipeptide precursors. Interestingly, N,N'-dimethylated rhodotorulic acid was found to be more soluble in various organic solvents than rhodotorulic acid. Moreover, erythrochelin was synthesized for the first time, and its metal-chelating ability with not only Fe(III) but also Mg(II) was confirmed based on electrospray ionization mass spectrometry (ESI-MS) analysis. Finally, we synthesized DKPs bearing a primary amino group, and found that they could catalyze the asymmetric aldol reaction between hydroxyacetone and p-nitrobenzaldehyde. (Keyword) Aldehydes / Catalysis / Chelating Agents / Crystallography, X-Ray / Cyclization / Diketopiperazines / Magnetic Resonance Spectroscopy / Methylation / Microwaves / Molecular Conformation / Oligopeptides / Organic Chemistry Phenomena / Piperazines / Solvents / Spectrometry, Mass, Electrospray Ionization (Tokushima University Institutional Repository) ● Metadata: 114085 (Link to Publication Site) ● Publication site (DOI): 10.1248/yakushi.17-00176 (Link to Search Site for Scientific Articles) ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 29199259 ● Summary page in Scopus @ Elsevier: 2-s2.0-85037343536 (Tokushima University Institutional Repository: 114085, DOI: 10.1248/yakushi.17-00176, PubMed: 29199259, Elsevier: Scopus)
4.	Shigeki Sano and Michiyasu Nakao : Chemistry of 2.5-Diketopiperazine and its Bis-lactim Ether: a Brief Review, Heterocycles, Vol.91, No.7, 1349-1375, Jul. 2015. (Summary) 2,5-Diketopiperazines have attracted much attention because of their biological activities and molecular structure characteristics. Bis-lactim ethers derived from these 2,5-diketopiperazines include well-known organic molecules such as Schöllkopf chiral auxiliaries, which are used in asymmetric synthesis of -amino acids. In this article, we briefly discuss the chemistry of both heterocyclic compounds. (Keyword) 2,5-diketopiperazine / 2,5-DKP / bis-lactim ether / 3,6-dialkoxy-2,5-dihydropyrazine / alpha-substituted serine (Link to Publication Site) ● Publication site (DOI): 10.3987/REV-15-820 (Link to Search Site for Scientific Articles) ● Summary page in Scopus @ Elsevier: 2-s2.0-84936818791 (DOI: 10.3987/REV-15-820, Elsevier: Scopus)
5.	Shigeki Sano and Michiyasu Nakao : 化学レビュー:多彩に機能するジケトピペラジン, 化学, Vol.67, No.2, 48-52, Jan. 2012.

Proceeding of International Conference:

1.	Shota Fujimoto, Naoki Muguruma, Michiyasu Nakao, Yoshihiko Miyamoto, Tatsuhiro Ishida, Shigeki Sano and Tetsuji Takayama : Near-Infrared Molecular Imaging of Gastrointestinal Stromal Tumors using a Novel Fluorescent Probe Indocyanine Green (ICG)-Labeled Dasatinib., Digetive Disease Week2018, Washington, D.C., Jun. 2018.
2.	Tamotsu Tanaka, M Md Rahman, E Iga, R Yamashita, R Shimizu, K Tsuji, A Shimada, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : Plasma level of ceramide 1-phosphate and its anti-apoptotic activity., 58th International conference on the bioscience of lipids (ICBL), Sep. 2017.
3.	M Md Rahman, A Shimada, Tohru Miyazaki, K Tsuji, Michiyasu Nakao, Shigeki Sano, Kentaro Kogure and Tamotsu Tanaka : Characterization of the Biological Effects of Ceramide-1-Phosphate., 第58回日本生化学会中国・四国支部例会, May 2017.
4.	Michiyasu Nakao and Shigeki Sano : Development of a Novel Method to Determine the Absolute Configuration of alpha-Amino Acids Based on 1H NMR Spectra of Diketopiperazines, The 8th AFMC International Medicinal Chemistry Symposium (AIMECS 11), Awaji, Nov. 2011.
5.	Takashi Ichikawa, Michiyasu Nakao and Shigeki Sano : Microwave-Assisted Deconjugative Esterification of ,-Unsaturated Carboxylic Acids, The Second Decennial Meeting between Seoul National University and the University of Tokushima, Awaji, Dec. 2010.
6.	Takeshi Tsumura, Masashi Horibe, Michiyasu Nakao and Shigeki Sano : Catalytic Asymmetric Ring-Opening of -Symmetric Cyclic Carbonates with Chiral Brnsted Acid Catalysts, The Second Decennial Meeting between Seoul National University and the University of Tokushima, Awaji, Dec. 2010.
7.	Michiyasu Nakao, Masanori Takeyasu, Shigeki Sano and Yoshimitsu Nagao : Synthesis of Optical Active Diketopiperazines for Absolute Configuration Determination of α-Amino Acids, The 12th Japan-Korea Joint Symposium on Drug Design and Development, Sendai, May 2008.
8.	Shigeki Sano, Michiyasu Nakao and Yoshimitsu Nagao : Novel Enantiodivergent Synthesis of α-Methylserine Derivatives Utilizing Enzymatic Acetylation, Seoul National University-The University of Tokushima Young Medicinal Chemist Symposium - Recent Status and Future Prospect of Medicinal Chemistry, Seoul, Jul. 2005.

Proceeding of Domestic Conference:

1.	Michiyasu Nakao, Ken Horikoshi and Shigeki Sano : Efficient one-pot, three-step synthesis of 1,2,3,5-tetrasubstituted pyrroles via aza-Michael addition of secondary amines to methyl 3-iminoacrylates, 日本薬学会第144年会, Mar. 2024.
2.	Kinari Hayashi, Mizune Ohzono, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 新規ビタミンE誘導体の構造安定性と脂肪蓄積抑制効果, 第33回ビタミンE研究会, Jan. 2024.
3.	Michiyasu Nakao, Ken Horikoshi, Takumi Natsuura, Ryutaroh Inui and Shigeki Sano : 3-イミノアクリル酸メチルのヘテロ-マイケル付加反応を起点とする多置換ヘテロ環合成, 49th Symposium on Progress in Organic Reactions and Synthesis Application in the Life Sciences, Nov. 2023.
4.	Ryutaroh Inui, Michiyasu Nakao and Shigeki Sano : 3-イミノアクリル酸メチルへのチア-マイケル付加反応で生じるジエステルの触媒的分子内環化反応による四置換チオフェンの合成, 第62回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2023.
5.	Moe Hirasawa, Michiyasu Nakao and Shigeki Sano : 1,3,2-チアザホスホリジン型新規HWE型試薬の合成と不斉HWE型反応への応用, 第62回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2023.
6.	Yuta Ashikawa, Chieko FUjii, Michiyasu Nakao and Shigeki Sano : ビス(オルガノアミノ)ホスホリル酢酸メチルとアルデヒドのジアステレオ分岐的HWE型反応, 第62回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2023.
7.	Shoki Yamada, Michiyasu Nakao and Shigeki Sano : ビス(オルガノチオ)ホスホリル酢酸メチルとアルデヒドのジアステレオ分岐的HWE型反応, 第62回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2023.
8.	Michiyasu Nakao, Ken Horikoshi and Shigeki Sano : 3-イミノアクリル酸メチルと第二級アミンのアザ-マイケル付加反応を起点とする四置換ピロールのワンポット三段階合成, 第62回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2023.
9.	Michiyasu Nakao, Ken Horikoshi, Takumi Matsuura, Ryutaroh Inui and Shigeki Sano : Synthesis of polysubstituted heterocycles via hetero-Michael addition of ketenimines, 第52回複素環化学討論会, Oct. 2023.
10.	林生成, 山﨑美沙季, Mizune Ohzono, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 安定性を向上させた新規ビタミン E 誘導体の脂肪蓄積抑制効果, 日本ビタミン学会第 75 回大会, Jun. 2023.
11.	YAMASAKI Misaki, YUIKA Seto, Mizune Ohzono, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : ジカルボン酸構造の最適化による安全で脂肪蓄積抑制作用を有する新規ビタミンE誘導体の開発, 日本薬学会第143年会, Mar. 2023.
12.	Kinari Hayashi, YAMASAKI Misaki, Mizune Ohzono, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 構造改変によるビタミンE誘導体の安定性の向上と脂肪蓄積抑制効果, 第32回ビタミンE研究会, Jan. 2023.
13.	Nath Manobendro Ray, Mizune Ohzono, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 炭素数一つの違いがビタミンE誘導体の細胞毒性を左右する, 第32回ビタミンE研究会, Jan. 2023.
14.	Shoki Yamada, Michiyasu Nakao and Shigeki Sano : ビス(ベンジルチオ)ホスホリル酢酸メチルとアルデヒドのHWE型反応における立体選択性の逆転現象, 第61回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2022.
15.	Chieko Fujii, Michiyasu Nakao and Shigeki Sano : ビス(オルガノアミノ)ホスホリル酢酸メチルとアルデヒドの立体選択的HWE型反応, 第61回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2022.
16.	Marie Okamoto, Michiyasu Nakao and Shigeki Sano : ビス(3,4,5-トリフルオロフェニル)ホスホノ酢酸メチルのリン原子上でのチオールによる求核置換反応, 第61回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2022.
17.	Ken Horikoshi, Michiyasu Nakao and Shigeki Sano : 3-イミノアクリル酸メチルのアザ-マイケル付加反応を起点とする四置換ピロールの合成, 第61回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2022.
18.	Mizune Ohzono, Misaki Yamasaki, Yuika Seto, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 安全で脂肪蓄積抑制作用を有する新規ビタミンE誘導体の開発, 日本ビタミン学会第74回大会, Jun. 2022.
19.	Michiyasu Nakao, Ryotaro Okazaki and Shigeki Sano : Stereoselective synthesis of methyl 3-(dialkoxyphosphoryl)acrylates via phospha-Michael addition of methyl 3-iminoacrylates, 日本薬学会第142年会, Mar. 2022.
20.	shota fujimoto, Naoki Muguruma, Michiyasu Nakao, Hidenori ANDO, takanori miyake, 樫原孝典, Tatsuhiro Ishida, Shigeki Sano and Tetsuji Takayama : 消化管間質腫瘍(GIST)に対する新たな内視鏡診断法の確立に向けた蛍光分子イメージング技術の開発, 第18回日本消化管学会学術集会, Feb. 2022.
21.	Shoki Yamada, Michiyasu Nakao and Shigeki Sano : ビス(ベンジルチオ)ホスホリル酢酸メチルとアルデヒドのE選択的HWE型反応, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
22.	Masaki Yamaguchi, Michiyasu Nakao and Shigeki Sano : 3-イミノアクリル酸メチルとシラノラートのオキサ-マイケル付加反応, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
23.	Chieko Fujii, Michiyasu Nakao and Shigeki Sano : ビス(ベンジルアミノ)ホスホリル酢酸メチルの合成とHWE型反応への応用, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
24.	Masakazu Tabaru, Michiyasu Nakao and Shigeki Sano : ビス(ベンジルチオ)ホスホリルプロピオン酸エチルとケテンのHWE型反応によるアレニルエステルの合成, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
25.	Shinnosuke Sozu, Michiyasu Nakao and Shigeki Sano : イソシアナートに対するHWE試薬の付加反応を用いる3-イミノアクリル酸エステルの合成, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
26.	Ryotaroh Okazaki, Michiyasu Nakao and Shigeki Sano : 3-イミノアクリル酸メチルのホスファ-マイケル付加反応による3-ジアルコキシホスホリルアクリル酸メチルの合成, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
27.	Marie Okamoto, Satoshi Isetani, Michiyasu Nakao and Shigeki Sano : フルオロフェノキシ基含有新規HWE試薬を用いた効率的混合ホスホン酸エステルの合成, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
28.	YAMASAKI Misaki, Tatsuya Fukuta, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 脂肪蓄積抑制作用を有する安全性の高い新規トコフェロールエステル体の開発, 第60回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2021.
29.	Mizune Ohzono, Nath Manobendoro Ray, YAMASAKI Misaki, Yuika Seto, Michiyasu Nakao, Tatsuya Fukuta, Shigeki Sano and Kentaro Kogure : ビタミンE誘導体による細胞死誘導機構の解明と安全な抗肥満薬開発への展開, 第42回生体膜と薬物の相互作用シンポジウム, Oct. 2021.
30.	YAMASAKI Misaki, Tatsuya Fukuta, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 新規ビタミンE エステル体の脂肪細胞に対する脂肪蓄積抑制効果, 日本ビタミン学会第73 回大会, Jun. 2021.
31.	Michiyasu Nakao, Koichi Ohtawa and Shigeki Sano : Synthesis of tetrasubstituted thiophenes via thia-Michael addition reaction of methyl 3-iminoacrylates, 日本薬学会第141年会, Mar. 2021.
32.	Marie Okamoto, Satoshi Isetani, Michiyasu Nakao and Shigeki Sano : 効率的混合ホスホン酸エステル合成を指向した新規HWE試薬の開発, 第59回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Dec. 2020.
33.	Masakazu Tabaru, Michiyasu Nakao and Shigeki Sano : ビス(ベンジルチオ)ホスホリル酢酸エステルとケテンのHWE型反応によるアレニルエステルの合成, 第59回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Dec. 2020.
34.	Shinnosuke Sozu, Michiyasu Nakao and Shigeki Sano : イソシアナートのHWE反応による3-イミノアクリル酸エステルの合成, 第59回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Dec. 2020.
35.	Koichi Otawa, Michiyasu Nakao and Shigeki Sano : 3-イミノアクリル酸メチルのチア-マイケル/ディークマン反応による四置換チオフェンの合成, 第59回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Dec. 2020.
36.	Takahito Ihara, Michiyasu Nakao and Shigeki Sano : ビス(オルガノチオ)ホスホリル酢酸メチルとアルデヒドのZ選択的HWE型反応, 第59回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Dec. 2020.
37.	Ken Horikoshi, Michiyasu Nakao and Shigeki Sano : 3-イミノアクリル酸エチルのアザ-マイケル付加反応を起点とする含窒素ヘテロ環の合成, 第59回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Dec. 2020.
38.	YAMASAKI Misaki, Dai Majima, Michiyasu Nakao, Shigeki Sano, Tatsuya Fukuta and Kentaro Kogure : 脂肪細胞の脂肪蓄積に対する種々のトコフェロールエステル体の効果, 日本ビタミン学会第72回大会, Sep. 2020.
39.	Masakazu Tabaru, Michiyasu Nakao and Shigeki Sano : Synthesis of allenyl esters by HWE-type reactions of methyl 2-[bis(benzylthio)phosphoryl]acetate and ketenes, 日本薬学会第140年会, Mar. 2020.
40.	Takahito Ihara, Michiyasu Nakao and Shigeki Sano : Stereoselective HWE-type reaction of aldehydes with methyl 2-[bis(benzylthio)phosphoryl]acetate, 日本薬学会第140年会, Mar. 2020.
41.	Akihito Nakamura, Michiyasu Nakao and Shigeki Sano : DOPOを求核剤とする安定型イソインドール誘導体の合成, 第58回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2019.
42.	Munehisa Toguchi, Michiyasu Nakao and Shigeki Sano : アレニルエステルの位置選択的チア-マイケル/ディークマン縮合反応による三置換チオフェンの合成, 第58回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2019.
43.	Michiyasu Nakao, Aumu Adachi and Shigeki Sano : シデロフォア活性物質エリスロケリンの立体異性体合成, 第58回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2019.
44.	Michiyasu Nakao, Ayumu Adachi and Shigeki Sano : Synthesis of Three Stereoisomers of Erythrochelin, a Hydroxamate-type Tetrapeptide Siderophore from Saccharopolyspora erythraea, 45th Symposium on Progress in Organic Reactions and Synthesis Application in the Life Sciences, Oct. 2019.
45.	Shota Fujimoto, Naoki Muguruma, Michiyasu Nakao, Hidenori ANDO, Yoshihiko Miyamoto, Koichi Okamoto, Yasushi Sato, Tatsuhiro Ishida, Shigeki Sano and Tetsuji Takayama : 新規蛍光プローブIndocyanine green (ICG) 標識Dasatinibを用いた消化管間質腫瘍 (GIST) の近赤外蛍光イメージング., 第14回日本分子イメージング学会総会・学術集会, May 2019.
46.	Michiyasu Nakao, Ayano Kishimoto and Shigeki Sano : Novel Phospha-Michael Addition of Phosphorus Nucleophiles to Allenyl Esters, 日本薬学会第139年会, Mar. 2019.
47.	Reona Shirakawa, Michiyasu Nakao and Shigeki Sano : Garegg-Samuelsson条件下での2-フルオロ-2-ジエチルホスホノ酢酸エチル誘導体の合成, 第57回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2018.
48.	Kazumasa Seki, Michiyasu Nakao and Shigeki Sano : ビス(オルガノチオ)ホスホリル酢酸メチルの合成とHWE型反応への応用, 第57回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2018.
49.	Michiyasu Nakao, Munehisa Toguchi, Yuki Shimabukuro, Ayano Kisimoto, Ken Horikoshi, Koichi Ohtawa and Shigeki Sano : Synthesis of Five-membered Heterocycles via Hetero-Michael Addition of Allenyl Esters, 44th Symposium on Progress in Organic Reactions and Synthesis Application in the Life Sciences, Nov. 2018.
50.	Shota Fujimoto, Naoki Muguruma, Koichi Okamoto, Yasushi Sato, Yoshihiko Miyamoto, Michiyasu Nakao, Shinji Kitamura, Hiroshi Miyamoto, Shigeki Sano, Tatsuhiro Ishida, Koichi Tsuneyama and Tetsuji Takayama : Theranostics理論に基づく消化管間質腫瘍(GIST)の新規診断治療法の開発., 第26回日本消化器関連学会週間(第96回日本消化器内視鏡学会総会), Nov. 2018.
51.	宮﨑徹, 島田明奈, 高橋尚子, Md. Motiur Rahman, 清水良多, 辻和樹, 森戸克弥, 山下量平, Shigeki Sano, Michiyasu Nakao, Tatsuya Fukuta, Kentaro Kogure and Tamotsu Tanaka : 外因的に加えた極長鎖脂肪酸およびこれを含有するセラミドのアポトーシスへの影響, 第11回セラミド研究会, Oct. 2018.
52.	Tohru Miyazaki, Akina Shimada, Naoko Takahashi, Rahman Motiur Md., Ryota Shimizu, Kazuki Tsuji, Katsuya Morito, Ryouhei Yamashita, Shigeki Sano, Michiyasu Nakao, Tatsuya Fukuta, Kentaro Kogure and Tamotsu Tanaka : 外因的に加えた極長鎖脂肪酸および極長鎖脂肪酸含有セラミドのアポトーシスへの影響, 第60回日本脂質生化学会, May 2018.
53.	Michiyasu Nakao, Munehisa Toguchi and Shigeki Sano : Tandem Thia-Michael/Dieckmann Condensation of Methyl Mercaptoacetate with Allenyl Esters, 日本薬学会第138年会, Mar. 2018.
54.	辻和樹, 島田明奈, 宮崎徹, 高橋尚子, 伊賀永里奈, Rahman Md Motiur, Michiyasu Nakao, Shigeki Sano, Kentaro Kogure and Tamotsu Tanaka : 種々の脂肪酸残基を有するセラミドの化学合成とその生理活性, 第40回日本分子生物学会年会，第90回日本生化学会大会プログラム, 438, Dec. 2017.
55.	Michiyasu Nakao, Munehisa Toguchi and Shigeki Sano : Tandem Thia-Michael/aldol-type Reaction of Allenyl Esters, 43nd Symposium on Progress in Organic Reactions and Synthesis Application in the Life Sciences, Nov. 2017.
56.	Tomomi Shozui, Daisuke Inoue, Michiyasu Nakao and Shigeki Sano : キラル第三級アミン触媒を用いるσ対称環状炭酸エステルの不斉開環反応, 第56回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2017.
57.	Munehisa Toguchi, Michiyasu Nakao and Shigeki Sano : アレニルエステルのチア-マイケル/ディークマン縮合反応による多置換チオフェン誘導体の合成, 第56回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2017.
58.	島田明奈, Tohru Miyazaki, 高橋尚子, Rahman Motiur Md., 清水良多, 辻和樹, 山下量平, Shigeki Sano, Michiyasu Nakao, Tatsuya Fukuta, Kentaro Kogure and Tamotsu Tanaka : 極長鎖脂肪酸およびこれを含有するセラミドのアポトーシス抑制活性, セラミド研究会, Oct. 2017.
59.	Tamotsu Tanaka, Md Motiur Rahaman, 伊賀永理奈, 山下量平, 清水良多, 辻和樹, 島田明奈, Michiyasu Nakao, Shigeki Sano and Kentaro Kogure : 血液中に存在する極長鎖セラミド-1-リン酸のアポトーシス抑制作用, 第59回日本脂質生化学会, 講演要旨集, 33-34, Jun. 2017.
60.	Shota Fujimoto, Naoki Muguruma, Yoshihiko Miyamoto, Michiyasu Nakao, Shigeki Sano, Hidenori ANDO, Tatsuhiro Ishida and Tetsuji Takayama : KIT分子を標的としたGISTの分子イメージング, 第103回日本消化器病学会総会, Apr. 2017.
61.	Michiyasu Nakao, Munehisa Toguchi and Shigeki Sano : Tandem thia-Michael/aldol Reaction of Mercaptoacetaldehyde with Allenyl Esters, 日本薬学会第137年会, Mar. 2017.
62.	Akihito Nakamura, Michiyasu Nakao and Shigeki Sano : Concentration Dependent Specific Rotations of Chiral Glycerol Derivatives, 日本薬学会第137年会, Mar. 2017.
63.	Michiyasu Nakao, Kazue Tanaka and Shigeki Sano : Synthesis of fluorine-containing analogs of 1-lysoglycerophospholipids via Horner-Wadsworth-Emmons reaction, 42nd Symposium on Progress in Organic Reactions and Synthesis Application in the Life Sciences, Nov. 2016.
64.	Munehisa Toguchi, Michiyasu Nakao and Shigeki Sano : 多置換テトラヒドロチオフェン合成を指向したタンデム型チア-マイケル/アルドール反応, 第74回パネル討論会 : 次世代を切り拓く全合成研究の若い力, Oct. 2016.
65.	Munehisa Toguchi, Michiyasu Nakao and Shigeki Sano : Synthesis of highly functionalized tetrahydrothiophenes by tandem the-Michael/aldol reaction of allonym esters, 46th Congress of Heterocyclic Chemistry, Sep. 2016.
66.	山下量平, 伊賀永里奈, 柿内直哉, 辻和樹, 小暮健太郎, Akira Tokumura, Michiyasu Nakao, Shigeki Sano and Tamotsu Tanaka : 種々のセラミド-1-リン酸分子種の生理活性とその代謝, 第58回日本脂質生化学会, Jun. 2016.
67.	Michiyasu Nakao, Shunsuke Tsuji and Shigeki Sano : Synthesis of Erythrochelin, a Hydroxamate-Type Siderophore, 日本薬学会第136年会, Mar. 2016.
68.	Akihito Nakamura, Michiyasu Nakao and Shigeki Sano : Synthesis of cis-Tetrahydrophthalazinones via Asymmetric Methanolysis of Cyclic Dicarboxylic Anhydride, 日本薬学会第136年会, Mar. 2016.
69.	Munehisa Toguchi, Michiyasu Nakao and Shigeki Sano : Tandem Thia-Michael/Aldol Reactions of Mercaptoaldehydes with Allenyl Esters, 日本薬学会第136年会, Mar. 2016.
70.	Akihito Nakamura, Michiyasu Nakao and Shigeki Sano : cis-テトラヒドロフタラジノン誘導体の効率的不斉合成法の開発, 第54回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2015.
71.	Munehisa Toguchi, Michiyasu Nakao and Shigeki Sano : アレニルエステルを用いる多置換テトラヒドロチオフェン類の合成, 第54回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2015.
72.	Kazue Tanaka, Michiyasu Nakao and Shigeki Sano : 含フッ素1-リゾホスファチジン酸ミメティクスの合成, 第54回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2015.
73.	Michiyasu Nakao, Tomoya Matsumoto, Munehisa Toguchi and Shigeki Sano : Synthesis of Allenyl Esters by Horner-Wadsworth-Emmons Reactions of Ketenes, 第41回反応と合成の進歩シンポジウム, Oct. 2015.
74.	Michiyasu Nakao, Shintaro Fukayama, Shunsuke Tsuji and Shigeki Sano : Facile Synthesis of Rhodotorulic Acid and Its Related Derivatives, 第40回反応と合成の進歩シンポジウム, Nov. 2014.
75.	Michiyasu Nakao, Shintaro Fukayama, Syunsuke Tsuji and Shigeki Sano : マイクロ波を活用したロドトルラ酸の効率的合成, 第53回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2014.
76.	Keisuke Matsuura, Michiyasu Nakao and Shigeki Sano : Facile Microwave-assisted Synthesis of Imidazo[2,1-b][1,3,4]thiadiazoles, 日本薬学会第134年会, Mar. 2014.
77.	Murasaki Miyagi, Shohei Inoue, Michiyasu Nakao and Shigeki Sano : Synthesis of Stable 2H-Isoindole Derivatives Based on Steric Protection Strategy, 日本薬学会第134年会, Mar. 2014.
78.	Tomoya Matsumoto, Michiyasu Nakao and Shigeki Sano : Stereoselective Synthesis of 2-Cyclopentylidene-2-fluoroactic Acid Derivatives by HWE Reaction, 第39回反応と合成の進歩シンポジウム, Nov. 2013.
79.	Tomoya Matsumoto, Michiyasu Nakao and Shigeki Sano : 2-フルオロ-2-ジエチルホスホノ酢酸エステルと2-OBO-シクロペンタノンのE選択的HWE反応, 第52回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2013.
80.	Keisuke Matsuura, Michiyasu Nakao and Shigeki Sano : マイクロ波を活用した2-アミノイミダゾチアジアゾール誘導体の効率的合成, 第52回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2013.
81.	Yosuke Wada, Michiyasu Nakao and Shigeki Sano : N-メチルジケトピペラジン型有機触媒によるヒドロキシアセトンと置換ベンズアルデヒドの不斉アルドール反応, 第52回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Oct. 2013.
82.	Murasaki Miyagi, Mitsutaka Kimura, Shohei Inoue, Michiyasu Nakao, Shigeki Sano, Makoto Fukui and Hiro-O Ito : A Modified OPA Method for a Valid Measure of Oral Malodor, 第11回プロセス化学東四国フォーラムセミナー, Jun. 2013.
83.	Murasaki Miyagi, Mitsutaka Kimura, Shohei Inoue, Michiyasu Nakao, Shigeki Sano, Makoto Fukui and Hiro-O Ito : A Modified OPA Method for a Valid Measure of Oral Malodor, 日本薬学会第133年会, Mar. 2013.
84.	Atsushi Handa, Michiyasu Nakao and Shigeki Sano : Synthesis of Optically Active Glycerophospholipids Using HWE Reagents (2), 日本薬学会第133年会, Mar. 2013.
85.	Tomoya Matsumoto, Michiyasu Nakao and Shigeki Sano : Stereoselective HWE Reaction of 2-Fluoro-2-diethylphosphonoacetic Acid with Ketones, 日本薬学会第133年会, Mar. 2013.
86.	Ryosuke Wada, Michiyasu Nakao and Shigeki Sano : 機能性分子を指向するN-メチルジケトピペラジンの合成研究, 第51回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2012.
87.	Murasaki Miyagi, Mitsutaka Kimura, Shohei Inoue, Michiyasu Nakao, Shigeki Sano, Makoto Fukui and Hiro-O Ito : オルトフタルアルデヒド法を基盤とした新規メチルメルカプタン蛍光標識法, 第51回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2012.
88.	Tomoya Matsumoto, Michiyasu Nakao and Shigeki Sano : 2-シクロペンチリデン-2-フルオロ酢酸誘導体の立体選択的合成, 第51回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2012.
89.	Atsushi Handa, Michiyasu Nakao and Shigeki Sano : HWE反応を鍵反応とする光学活性ホスファチジン酸の合成, 第51回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2012.
90.	Atsushi Handa, Michiyasu Nakao and Shigeki Sano : Synthesis of Optically Active Glycerophospholipids via HWE Reaction, 第38回反応と合成の進歩シンポジウム, Nov. 2012.
91.	Shintaro Fukayama, Michiyasu Nakao and Shigeki Sano : Synthetic Development of Iron-Chelating Agents Based on Rhodotorulic Acid, a Diketopiperazine Derivative, 第42回複素環化学討論会, Oct. 2012.
92.	Tomoya Matsumoto, Michiyasu Nakao and Shigeki Sano : Synthesis of Allenecarboxylic Acid Derivatives Based on HWE Reagents, 日本薬学会第132年会, Mar. 2012.
93.	Shintaro Fukayama, Michiyasu Nakao and Shigeki Sano : Synthesis of Iron-Chelating Agents Based on N-Methyldiketopiperazine Structure, 日本薬学会第132年会, Mar. 2012.
94.	Atsushi Handa, Michiyasu Nakao and Shigeki Sano : Synthesis of Optically Active Glycerophospholipids Using HWE Reagents, 日本薬学会第132年会, Mar. 2012.
95.	Michiyasu Nakao, Masanori Takeyasu, Yuriko Toriuchi, Yoshimitsu Nagao and Shigeki Sano : N-Methyldiketopiperazine Catalyzed Direct Asymmetric Aldol Reaction, 日本薬学会第132年会, Mar. 2012.
96.	Tomoya Matsumoto, Michiyasu Nakao and Shigeki Sano : 2-アシル-2-ホスホノ酢酸エステルを用いるアレニルエステル合成, 第50回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2011.
97.	Shintaro Fukayama, Yuriko Toriuhi, Michiyasu Nakao and Shigeki Sano : フェニルアラニン由来N-メチルジケトピペラジンのCH/π相互作用, 第50回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2011.
98.	Atsushi Handa, Michiyasu Nakao and Shigeki Sano : 混合ホスホン酸エステルを鍵中間体とするグリセロリン脂質の効率的化学合成, 第50回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2011.
99.	Takashi Ichikawa, Michiyasu Nakao and Shigeki Sano : 2-(1,3-ジオキサン-5-イリデン)酢酸の脱共役エステル化反応, 第50回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2011.
100.	Michiyasu Nakao, Yuriko Toriuchi, Shintaro Fukayama and Shigeki Sano : フェニルアラニン由来ジケトピペラジンのCH/π相互作用, 第50回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2011.
101.	Michiyasu Nakao, Yuriko Toriuchi, Shintaro Fukayama, Yuta Hiroyama and Shigeki Sano : Folded Conformation of Diketopiperazines Based on Intramolecular CH/ Interaction, 第37回反応と合成の進歩シンポジウム, Nov. 2011.
102.	半田充史, 時實梨衣, Michiyasu Nakao and Shigeki Sano : HWE反応を基盤とする効率的なグリセロリン脂質の合成法の開発, 創薬懇話会2011, Jul. 2011.
103.	Michiyasu Nakao, 鳥内有里子, 廣山裕太 and Shigeki Sano : ジケトピペラジンの折りたたみ型立体配座とCH/π相互作用, 創薬懇話会2011, Jul. 2011.
104.	難波建多郎, Daisuke Tsuji, 金城奈美, Michiyasu Nakao, Shigeki Sano and Kouji Itou : 未分化細胞に対する新規分化誘導剤の探索, 第52回日本生化学会中国・四国支部総会, May 2011.
105.	Atsushi Handa, Rie Tokizane, Michiyasu Nakao and Shigeki Sano : Synthesis of Glycerophospholipids via Horner-Wadsworth-Emmons Reaction (2), 日本薬学会第131年会, Mar. 2011.
106.	Shota Tempaku, Hiroshi Nanataki, Michiyasu Nakao and Shigeki Sano : Synthesis of N-Cbz-Gly-[(Z)-CF=C]-Pro-OH via Horner-Wadsworth-Emmons Reaction, 日本薬学会第131年会, Mar. 2011.
107.	Masashi Horibe, Takeshi Tsumura, Michiyasu Nakao and Shigeki Sano : Asymmetric Ring-Opening of -Symmetric Cyclic Carbonates Using Chiral Brnsted Acid Catalysts, 日本薬学会第131年会, Mar. 2011.
108.	Takashi Ichikawa, Michiyasu Nakao and Shigeki Sano : Microwave-Promoted Deconjugative Esterification of ,-Unsaturated Carboxylic Acids, 日本薬学会第131年会, Mar. 2011.
109.	Michiyasu Nakao, Yuriko Toriuchi, Yuta Hiroyama and Shigeki Sano : Substituent Effects on Folded Conformation of Diketopiperazines, 日本薬学会第131年会, Mar. 2011.
110.	Junichi Shigemori, Kaori Ueda, Michiyasu Nakao, Shigeki Sano, Kiyoshi Satouchi and Akira Tokumura : 卵白リゾホスホリパーゼ D により産生されるリゾホスファチジン酸の卵黄嚢の血管系形成作用, BMB2010 ∼ 第33回日本分子生物学会年会・第83回日本生化学会大会合同大会, Dec. 2010.
111.	Michiyasu Nakao, Yuta Hiroyama, Yuriko Toriuchi and Shigeki Sano : Conformational Analysis of N-Methyldiketopiperazines for Investigating the Intramolecular Interaction, 第40回複素環化学討論会, Nov. 2010.
112.	Takeshi Tsumura, Masashi Horibe, Michiyasu Nakao and Shigeki Sano : キラルブレンステッド酸触媒によるσ対称環状炭酸エステルの触媒的不斉開環反応, 第49回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2010.
113.	Shota Tempaku, Hiroshi Nanataki, Michiyasu Nakao and Shigeki Sano : HWE反応を基盤とするグリシルプロリンミメティクス合成法の開発, 第49回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2010.
114.	Takashi Ichikawa, Michiyasu Nakao and Shigeki Sano : カルボジイミド型脱水縮合剤を用いる2-ペンテン酸の脱共役エステル化反応, 第49回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2010.
115.	Atsushi Handa, Rie Tokizane, Michiyasu Nakao and Shigeki Sano : HWE反応を基盤とするグリセロリン脂質合成法の開発, 第49回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2010.
116.	Michiyasu Nakao, Yuta Hiroyama, Yuriko Toriuchi and Shigeki Sano : 芳香環含有ジケトピペラジン類のコンホメーション解析, 第49回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2010.
117.	Takashi Ichikawa, Michiyasu Nakao and Shigeki Sano : Deconjugative Esterification of ,-Unsaturated Carboxylic Acids through Intramolecular Chirality Transfer, 第36回反応と合成の進歩シンポジウム, Nov. 2010.
118.	Takeshi Tsumura, Masashi Horibe, Michiyasu Nakao and Shigeki Sano : Catalytic Asymmetric Ring-Opening of -Symmetric Cyclic Carbonates (2), 日本薬学会第130年会, Mar. 2010.
119.	Teppei Yano, Michiyasu Nakao and Shigeki Sano : Synthesis of Allenic Esters by HWE Reactions Based on Still's Reagent, 日本薬学会第130年会, Mar. 2010.
120.	Yuta Hiroyama, Michiyasu Nakao and Shigeki Sano : Synthesis of Diketopiperazines for Determining Absolute Configuration of -Amino Acids (4), 日本薬学会第130年会, Mar. 2010.
121.	Yukari Nakayama, Hiroshi Kouno, Michiyasu Nakao and Shigeki Sano : An Improved Synthesis of Anguibactin and Its Derivatives, 日本薬学会第130年会, Mar. 2010.
122.	Ryosuke Sakai, Michiyasu Nakao and Shigeki Sano : Synthetic Development of Fluorescent Labeling Agents Based on 3-Acylthiazolidine-2-thione, 日本薬学会第130年会, Mar. 2010.
123.	Takashi Ichikawa, Michiyasu Nakao and Shigeki Sano : Deconjugative Esterification of Acyclic ,-Unsaturated Carboxylic Acids, 日本薬学会第130年会, Mar. 2010.
124.	Takeshi Tsumura, Masashi Horibe, Michiyasu Nakao and Shigeki Sano : Catalytic Asymmetric Ring-Opening of -Symmetric Cyclic Carbonates (1), 日本薬学会第130年会, Mar. 2010.
125.	Michiyasu Nakao, Yuta Hiroyama, Tatsusada Yoshida, Hiroshi Chuman and Shigeki Sano : Conformational Analysis of N-Methyldiketopiperazines, 日本薬学会第130年会, Mar. 2010.
126.	Masahiro Kamura, Takeshi Tsumura, Michiyasu Nakao and Shigeki Sano : Synthesis of Optically Active 4a,5,8,8a-Tetrahydrophthalazin-1(2H)-one Derivatives, 日本薬学会第130年会, Mar. 2010.
127.	Teppei Yano, Michiyasu Nakao and Shigeki Sano : Still試薬のHWE反応によるアレン化合物の合成, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
128.	Yuta Hiroyama, Michiyasu Nakao and Shigeki Sano : N-メチルジケトピペラジン構造を基盤とするα-アミノ酸の絶対配置決定法の開発, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
129.	Yukari Nakayama, Hiroshi Kouno, Michiyasu Nakao and Shigeki Sano : シデロフォア活性物質アンギバクチンならびに関連誘導体の合成, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
130.	Ryosuke Sakai, Michiyasu Nakao and Shigeki Sano : 分子内励起二量体形成型タンパク質蛍光標識試薬の合成開発, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
131.	Masanori Kamura, Takeshi Tsumura, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : 環状酸無水物の不斉アルコリシスを基盤とする光学活性フタラジノンの合成, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
132.	Akinobu Morimoto, Michiyasu Nakao, Shigeki Sano and Hiro-O Ito : OPA法ならびにエルマン法を基盤とするチオール捕捉標識反応剤の合成開発, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
133.	Hiroshi Nanataki, Michiyasu Nakao and Shigeki Sano : フルオロオレフィン型プロリン含有ジペプチドミメティクス合成を目的とする立体選択的HWE反応, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
134.	Rie Tokizane, Michiyasu Nakao and Shigeki Sano : 1,2-ジグリセリド含有HWE試薬の合成とグリセロリン脂質への変換, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
135.	Daisuke Yamashita, Michiyasu Nakao and Shigeki Sano : タンデム型還元-オレフィン化反応によるE選択的オレフィン合成, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
136.	Takashi Ichikawa, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : DCCを用いるα,β-不飽和カルボン酸の脱共役エステル化反応, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
137.	Takeshi Tumura, Masashi Horibe, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : σ対称環状炭酸エステルの触媒的エナンチオ選択的開環反応, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
138.	Michiyasu Nakao, Yuta Hiroyama, Shigeki Sano and Yoshimitsu Nagao : 芳香環含有ジケトピペラジン類のコンホメーション解析, 第48回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会, Nov. 2009.
139.	Takashi Ichikawa, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : Deconjugative Esterification of α,β-Unsaturated Carboxylic Acids through Carbodiimide Coupling, 第35回反応と合成の進歩シンポジウム, Nov. 2009.
140.	Rie Tokizane, Michiyasu Nakao and Shigeki Sano : Synthesis of Glycerophospholipids via Horner-Wadsworth-Emmons Reaction, 日本薬学会第129年会, Mar. 2009.
141.	Takashi Ichikawa, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : Deconjugative Esterification of 2-Cyclohexylideneacetic Acids with Intramolecular Chiral Transfer, 日本薬学会第129年会, Mar. 2009.
142.	Michiyasu Nakao, Masanori Takeyasu, Yuta Hiroyama, Shigeki Sano and Yoshimitsu Nagao : Synthesis of Diketopiperazines for Determining Absolute Configuration of α-Amino Acids (3), 日本薬学会第129年会, Mar. 2009.
143.	Michiyasu Nakao, Masanori Takeyasu, Yuta Hiroyama, Shigeki Sano and Yoshimitsu Nagao : 複素環化合物の特性を活用したα-アミノ酸の簡便絶対配置決定法, 創薬懇話会2008, Dec. 2008.
144.	Michiyasu Nakao, Masanori Takeyasu, Yuta Hiroyama, Shigeki Sano and Yoshimitsu Nagao : Synthesis of Optical Active Diketopiperazines for Absolute Configuration Determination of α-Amino Acids, 第38回複素環化学討論会, Nov. 2008.
145.	Rie Tokizane, Michiyasu Nakao and Shigeki Sano : HWE反応を基盤とするグリセロリン脂質の合成研究, 第47回日本薬学会·日本薬剤師会·日本病院薬剤師会中国四国支部学術大会, Nov. 2008.
146.	Takashi Ichikawa, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : カルボジイミド型脱水縮合剤を用いるケテン経由の脱共役エステル化反応, 第47回日本薬学会·日本薬剤師会·日本病院薬剤師会中国四国支部学術大会, Nov. 2008.
147.	Michiyasu Nakao, Masanori Takeyasu, Yuta Hiroyama, Shigeki Sano and Yoshimitsu Nagao : 1H NMRを用いるα-アミノ酸の簡便絶対配置決定法の開発, 第47回日本薬学会·日本薬剤師会·日本病院薬剤師会中国四国支部学術大会, Nov. 2008.
148.	Takashi Ichikawa, Michiyasu Nakao, Shigeki Sano and Yoshimitsu Nagao : Deconjugative Esterification through Carbodiimide Coupling, 日本薬学会第128年会, Mar. 2008.
149.	Michiyasu Nakao, Masanori Takeyasu, Saori Nakano, Shigeki Sano and Yoshimitsu Nagao : Synthesis of Diketopiperazines for Absolute Configuration Determination of α-Amino Acids (2), 日本薬学会第128年会, Mar. 2008.
150.	Michiyasu Nakao, 竹安正範, 中野沙織, Shigeki Sano and Yoshimitsu Nagao : 1H NMRを活用するα-アミノ酸誘導体の新規絶対配置決定法の開発, 第46回日本薬学会·日本薬剤師会·日本病院薬剤師会中国四国支部学術大会, Nov. 2007.
151.	Michiyasu Nakao, 竹安正範, 中野沙織, Shigeki Sano and Yoshimitsu Nagao : 光学活性ジケトピペラジンの合成とα-アミノ酸誘導体の新規絶対配置決定法の開発, 第33回反応と合成の進歩シンポジウム, Nov. 2007.
152.	Michiyasu Nakao, Masanori Takeyasu, Shigeki Sano and Yoshimitsu Nagao : ジケトピペラジン構造を基盤とするα-アミノ酸の新規絶対配置決定法の開発研究, 日本薬学会第127年会, Mar. 2007.
153.	Michiyasu Nakao, 竹安正範, Shigeki Sano and Yoshimitsu Nagao : α-置換セリン誘導体のエナンチオ分岐的合成と新規絶対配置決定法の開発, 第32回反応と合成の進歩シンポジウム, Dec. 2006.
154.	Michiyasu Nakao, 竹安正範, Shigeki Sano and Yoshimitsu Nagao : α-置換セリン誘導体のエナンチオ分岐的化学-酵素合成ならびに絶対配置の決定, 第45回日本薬学会·日本病院薬剤師会中国四国支部学術大会, Oct. 2006.
155.	Michiyasu Nakao, 竹安正範, 山本千代, Shigeki Sano and Yoshimitsu Nagao : α-置換セリン誘導体のエナンチオ分岐的化学-酵素合成, 第7回長井長義記念シンポジウム, Sep. 2006.
156.	Shigeki Sano, Michiyasu Nakao, 山本千代 and Yoshimitsu Nagao : リパーゼを用いるα-置換セリン誘導体のエナンチオ分岐的合成, 日本薬学会第126年会, Mar. 2006.
157.	Shigeki Sano, Michiyasu Nakao, 山本千代 and Yoshimitsu Nagao : 酵素アシル化を用いるα-置換セリン誘導体のエナンチオ分岐的合成, 第44回日本薬学会·日本病院薬剤師会中国四国支部学術大会, Nov. 2005.
158.	Shigeki Sano, Michiyasu Nakao and Yoshimitsu Nagao : 酵素アセチル化反応を用いるα-メチルセリン誘導体のエナンチオ分岐的合成, 日本薬学会第125年会, Mar. 2005.
159.	Shigeki Sano, Michiyasu Nakao and Yoshimitsu Nagao : 酵素反応を用いるα-メチルセリン誘導体のエナンチオ分岐的合成, 第43回日本薬学会·日本病院薬剤師会中国四国支部学術大会, Nov. 2004.

Patent:

1.	Jumpei Teramachi, Michiyasu Nakao, Shigeki Sano, Masahiro Abe and Takeshi Harada : PIM2阻害剤, 2021- 14411 (Feb. 2021), 110000796 (Feb. 2021).

Grants-in-Aid for Scientific Research (KAKEN Grants Database @ NII.ac.jp)

α,β-不飽和エステルのジアステレオ分岐的合成を可能とする新規ＨＷＥ型試薬の創製 (Project/Area Number: 23K06026 )
Development of novel Horner-Wadsworth-Emmons type reagents with phosphorus-sulfur single bonds (Project/Area Number: 20K06966 )
Development of novel molecular transformation based on the hetero-Michael reaction of ketenimine (Project/Area Number: 20K06940 )
Development of novel asymmetric catalyst based on piperazinone derivatives (Project/Area Number: 15K18829 )
Development of a novel high sensitivity molecular imaging for ACF (Project/Area Number: 26293176 )
Development of Synthetic Methods of Glycerophospholipids Using HWE Reaction as a Key Reaction (Project/Area Number: 23590007 )
Development of high-throughput analysis formouth odor (Project/Area Number: 22592336 )
Search by Researcher Number (60550001)

Associate Professor : Nakao, Michiyasu

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Grants-in-Aid for Scientific Research (KAKEN Grants Database @ NII.ac.jp)