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Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents
Journal article

Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents

Jih Ru Hwu, Long‐Li Lai, Gholam H. Hakimelahi and Hady Davari
Helvetica Chimica Acta, Vol.77(4), pp.1037-1045
1994

Abstract

Syntheses of the cis‐configurated isodethiaselenapenam 5 (Scheme 1) as well as the isodethiaselenacephems 29 and 31 (Scheme 2) were accomplished, in which the key step involved addition of Se to the corresponding carbanions of 1, 25, and 27 followed by internal alkylation. β‐Lactams 29 and 31 were found to possess biological activity against several pathogenic microorganisms in vitro. The electronic activation of the lactam moiety in the isodethiaselenacephem 31 and the corresponding isocephem 33 remarkably enhanced their biological activity. Isodethiaselenacephem 31 was more toxic than isocephem 33 in experimental animals. Copyright © 1994 Verlag GmbH & Co. KGaA, Weinheim

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