Synthesis and Antibacterial Activity of New 1β-Methylcarbapenems Having the Potential for Intramolecular Nonbonded S…O Interactions

Yoshimitsu NAGAO; Hitoshi IIMORI; Ki Hong NAM; Shigeki SANO; Motoo SHIRO

doi:10.1248/cpb.49.1660

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Synthesis and Antibacterial Activity of New 1β-Methylcarbapenems Having the Potential for Intramolecular Nonbonded S…O Interactions

Yoshimitsu NAGAO, Hitoshi IIMORI, Ki Hong NAM, Shigeki SANO, Motoo SHIRO

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Keywords: carbapenem antibiotic, thiaddiazoline, X-ray analysis, crystallographic structure, close contact

JOURNAL FREE ACCESS

2001 Volume 49 Issue 12 Pages 1660-1661

DOI https://doi.org/10.1248/cpb.49.1660

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Abstract

Mercaptoacetyliminothiadiazoline derivatives (19, 20) useful for the pendant moiety of 1β-methylcarbapenem antibiotics were efficiently synthesized. Acetyl derivative (18) of 20 was submitted to X-ray analysis, and a significant nonbonded S…O close contact was recognized in the crystallographic structure. New 1β-methylcarbapenems (5, 6) were synthesized by exploiting 19 and 20, and exhibited considerable antibacterial activities in vitro.

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