A Novel 1β-Methylcarbapenem Antibiotic, S-4661 Synthesis and Structure-activity Relationships of 2-(5-Substituted Pyrrolidin-3-ylthio)-1β-methylcarbapenenis

YASUYOSHI Iso; TADASHI IRIE; YUTAKA NISHINO; KIYOSHI MOTOKAWA; YASUHIRO NISHITANI

doi:10.7164/antibiotics.49.199

A Novel 1β-Methylcarbapenem Antibiotic, S-4661

Synthesis and Structure-activity Relationships of 2-(5-Substituted Pyrrolidin-3-ylthio)-1β-methylcarbapenenis

YASUYOSHI Iso, TADASHI IRIE, YUTAKA NISHINO, KIYOSHI MOTOKAWA, YASUHIRO NISHITANI

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JOURNAL FREE ACCESS

1996 Volume 49 Issue 2 Pages 199-209

DOI https://doi.org/10.7164/antibiotics.49.199

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Abstract

The synthesis and biological activity of (1R, 5S, 6S)-2-[(3S, 5S)-5-substituted pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acids are described. These compounds exhibit potent antibacterial activity against a wide range of both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. Of these new carbapenems, (1R, 5S, 6S)-2-[(3S, 5S)-5-sulfamoylaminomethyl pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (S-4661) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.

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