Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems

Hisatoshi Shinagawa; Hiroshi Yamaga; Hitoshi Houchigai; Yoshihiro Sumita; Makoto Sunagawa

doi:10.1016/S0968-0896(96)00273-8

Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems

Hisatoshi Shinagawa, Hiroshi Yamaga, Hitoshi Houchigai, Yoshihiro Sumita, Makoto Sunagawa

University Hospital

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

A series of 1β-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1β-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I.

Original language	English
Pages (from-to)	601-621
Number of pages	21
Journal	Bioorganic and Medicinal Chemistry
Volume	5
Issue number	3
DOIs	https://doi.org/10.1016/S0968-0896(96)00273-8
Publication status	Published - Mar 1 1997

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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AU - Sumita, Yoshihiro

AU - Sunagawa, Makoto

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