Synthesis and antibacterial activity of some novel 6-methyl- and 6-propenyl-substituted carbapenems

The synthesis and antibacterial activity of a number of 6-methyl- and 6-propenyl-substituted carbapenems is described. The 6-(hydroxymethyl)- and 6-(aminomethyl)carbapenems possessed more potent antibacterial activity in vitro than their respective 6-(1'(R)-hydroxyethyl) or 6-(1'(R)-aminoe...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1992-03, Vol.35 (5), p.953-958
Main Authors: Mastalerz, Harold, Menard, Marcel, Ruediger, Edward, Fung-Tomc, Joan
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Anti-Bacterial Agents - therapeutic use
Bacteria - drug effects
Carbapenems - chemical synthesis
Carbapenems - pharmacology
Carbapenems - therapeutic use
Chemistry
Drug Stability
Escherichia coli Infections - drug therapy
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Mice
Molecular Structure
Organic chemistry
Preparations and properties
Pseudomonas aeruginosa
Stereoisomerism
Structure-Activity Relationship
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Summary:The synthesis and antibacterial activity of a number of 6-methyl- and 6-propenyl-substituted carbapenems is described. The 6-(hydroxymethyl)- and 6-(aminomethyl)carbapenems possessed more potent antibacterial activity in vitro than their respective 6-(1'(R)-hydroxyethyl) or 6-(1'(R)-aminoethyl) counterparts. However, because of reduced stability, the 6-(aminomethyl)carbapenem was found to be inactive in vivo. All 6-hydroxypropenyl or 6-aminopropenyl derivatives that were prepared were less active than their respective 6-heteroethyl-substituted analogues.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00083a022