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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)601-621
Number of pages21
JournalBioorganic and Medicinal Chemistry
Volume5
Issue number3
DOIs
Publication statusPublished - Mar 1 1997
Externally publishedYes

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Lactams
Carbapenems
Methicillin-Resistant Staphylococcus aureus
Skeleton
1 beta-methylcarbapenem

ASJC Scopus subject areas

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

Cite this

Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems. / Shinagawa, Hisatoshi; Yamaga, Hiroshi; Houchigai, Hitoshi; Sumita, Yoshihiro; Sunagawa, Makoto.

In: Bioorganic and Medicinal Chemistry, Vol. 5, No. 3, 01.03.1997, p. 601-621.

Research output: Contribution to journalArticle

Shinagawa, Hisatoshi ; Yamaga, Hiroshi ; Houchigai, Hitoshi ; Sumita, Yoshihiro ; Sunagawa, Makoto. / Synthesis and biological properties of a new series of anti-MRSA β-Lactams; 2-(thiazol-2-ylthio)carbapenems. In: Bioorganic and Medicinal Chemistry. 1997 ; Vol. 5, No. 3. pp. 601-621.
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