1993 Fiscal Year Final Research Report Summary
Development of Novel Polyyne Antibiotic Agent
| Project/Area Number |
04554018
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
YAMAGUCHI Masahiko TOHOKU UNIVERSITY, Faculty of Science, Assistant Professor, 理学部, 助教授 (30158117)
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| Co-Investigator(Kenkyū-buntansha) |
HIRAOKA Tetsuo 三共(株), 活性物質研究所, 所長
HIRAMA Masahiro 東北大学, 理学部, 教授 (30165203)
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| Project Period (FY) |
1992 – 1993
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| Keywords | Conjugated polyyne / Caryoynencins / Total synthesis / Octatetrayne / Antibacterial / 1-Alkyne / Alkynylation / SnCl_4 |
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| Research Abstract |
This project aims at the investigation of chemistry on conjugated polyyne compounds and the development of polyyne antibacterial agent. Advances were made on the following subjects during the period of the financial support.
1) A new methodology for the synthesis of conjugated polyyne compounds
Monosilylated 1, 3, 5, 7-octatetrayne and 1, 3, 5-hexatriyne were prepared, and their lithiation, nucleophilic alkynylation, and aryl coupling were examined. A polymer film obtained by polymerization of a tetrayne showed conductivity of 10^<-3> Scm^<-1> when doped with SO_3.
2) A novel activation method of acetylenic C-H
Alkynylation reactions of aldehydes, acetals, and enones with 1-alkynes in the presence of SnCl_4 and Bu_3N were developed. During the studies, "carbostannylation" reaction of carbon-carbon triple bonds was discovered, which was applied to the stereoselective synthesis of tetrasubstituted enones and the direct vinylation of phenols. Both were unsolved problems in organic synthesis.
3) Synthesis and biological activities of caryoynencins and related compounds
Polyyne antibiotics caryoynencins and related compounds were synthesized, and their antibacterial activities were studied. An analog lacking (CH_2)_3COOH moiety of the natural product showed potent activities against bacteria and fungi including MRSA.Another analog in which tetrayne part and diene part does not conjugated each other exhibited potent activities towards Tricophyton. It was shown that the tetrayne moiety is essential for the biological activities.
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[Publications] M.Yamaguchi,H.-J.Park,M.Hirama,K.Torisu,H.Nishihara,and T.Hiraoka: "Synthesis and Reactions of Monosilylated 1,3,5-Hexatriyne and 1,3,5,7-Octatetrayne.Total Synthesis of Caryoynencins." Bull.Chem.Soc.Jpn.,in press.
Description
「研究成果報告書概要(和文)」より
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[Publications] M.Yamaguchi, H.-J.Park, M.Hirama, K.Torisu, S.Nakamura, T.Minami, H.Nishihara, and T.Hiraoka: "Synthesis and Reactions of Monosilylated 1, 3, 5-Hexatriyne and 1, 3, 5, 7-Octatetrayne. Total Synthesis of Caryoynencins." Bull.Chem.Soc.Jpn.(in press).
Description
「研究成果報告書概要(欧文)」より
