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Syntheses of New Isocephems and Isodethiaoxacephems as Antimicrobial Agents
Author(s) -
Hakimelahi Gholam H.,
Hwu Jih Ru,
Tsay ShwuChen,
Ramezani Zahra,
Hwu Jih Ru
Publication year - 1996
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.19960790323
Subject(s) - chemistry , antimicrobial , carbanion , moiety , alkylation , in vitro , lactam , biological activity , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , catalysis
Abstract The cis ‐configurated isocephem 26 as well as isodethiaoxacephems 21 and 33 were synthesized ( Schemes 4 and 5 ). The key step involves chlorination of the corresponding carbanions of 23, 18 , and 31 with CF 3 SO 2 Cl followed by internal alkylation. β‐Lactams 3, 21, 26 , and 33 were found to possess biological activity against several pathogenic microorganisms in vitro . Electronic activation of the lactam moiety in isodethiaoxacephem 33 remarkably enhanced its biological activity.