6-(substituted methylene)penems, potent broad spectrum inhibitors of bacterial β-lactamase: III. structure-activity relationships of the 5-membered heterocyclic derivatives

Abstract

Sodium (5RS)-Z-6-(heterocyclylmethylene)penem-3-carboxylates (2) are a series of extremely potent inhibitors of bacterial β-lactamases. A variety of 5-membered heteroaromatic derivatives have been prepared and structure-activity studies reveal a preferred substituent orientation. One of these derivatives, the 1-methyl-1,2,3-triazolyl compound (5m) is a more potent synergist of amoxycillin than clavulanic acid, sulbactam or tazobactam. © 1991, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.