2-Substituted Penems with Amino Acid-Related Side Chains: Synthesis and Antibacterial Activity of a New Series of. beta.-Lactam Antibiotics

…, P Sbraci, V Pestellini, F Arcamone…

Index: Altamura, Maria; Perrotta, Enzo; Sbraci, Piero; Pestellini, Vittorio; Arcamone, Federico; et al. Journal of Medicinal Chemistry, 1995 , vol. 38, # 21 p. 4244 - 4256

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Citation Number: 19

Abstract

A new series of 6-(hydroxyethy1) penems 2-substituted with amino acid-related side chains was synthesized. The nature of the amino acyl derivative proved to be crucial both from a synthetic point of view, as p-lactam ring opening can compete with C-2 nucleophilic substitution, and for antibacterial activity. Primary amino acid amides emerged as the most suitable side chains for enhancing permeability through a Gram-negative outer membrane ...