A NEW SERIES OF CARBAPENEM ANTIBIOTICS WITH 5'-SUBSTITUTED PYRROLIDINYLTHIO GROUP AT C-2 POSITION

In the preceding paper, we reported the synthesis and biological properties of carbapenem compounds having 5'-aminocarbonyl pyrrolidin-3'-ylthio group as C-2 side chain and demonstrated that SM-7338, (1R,5S,6S)-2-((3S,5S)-5-dimethylaminocarbonyl-pyrrolidin-3-ylthio) -6-((R)-1-hydroxyethyl)...

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Published inJournal of antibiotics Vol. 44; no. 4; pp. 459 - 462
Main Authors SUNAGAWA, MAKOTO, MATSUMURA, HARUKI, INOUE, TAKAAKI, FUKASAWA, MASATOMO, KATO, MASUHIRO
Format Journal Article
LanguageEnglish
Published Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 01.04.1991
Subjects
Carbapenems - chemical synthesis
Carbapenems - chemistry
Carbapenems - pharmacology
Chemical Phenomena
Chemistry
Microbial Sensitivity Tests
Molecular Structure
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Summary:In the preceding paper, we reported the synthesis and biological properties of carbapenem compounds having 5'-aminocarbonyl pyrrolidin-3'-ylthio group as C-2 side chain and demonstrated that SM-7338, (1R,5S,6S)-2-((3S,5S)-5-dimethylaminocarbonyl-pyrrolidin-3-ylthio) -6-((R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylic acid (1a), exhibited an extended antibacterial spectrum including anti-pseudomonal activity and high stability to renal dehydropeptidase-I (DHP-I). With the aim of further improving the stability to DHP-I, we studied the modification of the substituent on the pyrrolidine ring, that is, introducing a methylene spacer between aminocarbonyl group and pyrrolidine ring at the 5' position and exchanging the aminocarbonyl group with other functional groups such as hydroxyl and cyano groups.
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.44.459