Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems--I. 2-Alkoxymethyl derivatives

Bioorganic & Medicinal Chemistry
H AzamiM Murata

Abstract

The synthesis and in vitro antibacterial activity of a novel series of 2-alkoxymethyl-4-pyrrolidinylthio-1 beta-methyl carbapenems are described. As a result of these studies, we discovered that FR27743 (19j) containing a novel 2-fluoroethoxymethyl substituent possesses a broad spectrum of antibacterial activity against both Gram-positive and Gram-negative organisms, including Pseudomonas aeruginosa. Furthermore, FR27743 exhibited excellent stability against renal dehydropeptidase-I (DHP-I), good urinary recovery, and superior in vivo activity compared to that for Meropenem against several systemic infections.

References

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Related Concepts

Dipeptidase
3-(2-(2-fluoroethyloxymethyl)pyrrolidine-4-yl)thio-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
Metazoa
Dipeptidases
Drug Stability
Mouse, Inbred ICRC
Fungus Drug Sensitivity Tests
Pseudomonas Infections
Staphylococcal Infections
Thienamycins

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