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Syntheses of the First Selenium‐Containing Bicyclic β ‐Lactams as Potent Antimicrobial Agents
Author(s) -
Hwu Jih Ru,
Lai LongLi,
Hakimelahi Gholam H.,
Davari Hady
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770416
Subject(s) - chemistry , moiety , antimicrobial , lactam , selenium , bicyclic molecule , stereochemistry , alkylation , carbanion , in vitro , biological activity , combinatorial chemistry , organic chemistry , biochemistry , catalysis
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.