Studies on monocyclic β-lactam antibiotics: II. Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-oxysulfonic acids

Abstract

The synthesis and in vitro antibacterial and β-lactamase inhibitory activity of the 2-azetidinone-l-oxysulfonic acids havinga substituent at C-4 position of the β-lactam ring are described. The influence of C-4 substituents on the antibacterial activity wasexamined for the compounds having α-ureidoacetyl or α-oxyiminoacetyl group as acyl side chain at C-3 position. The antibacterial activity is correlated with the C-4 substituents and acyl side chain. Especially, 4(JR)-methyl substituted derivatives exhibited excellent activity against Gram-negative bacteria and4-dimethyl substituted derivatives exhibited strong activity against resistant Gram-negative bacteria except for Pseudomonas aeruginosa. 39 and 40 showed strong inhibitory activity against cephalosporinase of Enterobacter cloacae H-27. © 1985, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.