Studies on β-Lactam Antibiotics. III. Synthesis of 6-[D (-)-α-(Acylamino)-phenylacetamido] penicillanic Acids and Antibacterial Activity

Abstract

6-[D (-)-α-(Acylamino) phenylacetamido] penicillanic acids (1-34) were prepared by reacting ampicillin with the appropriated acylating derivatives of nitrogen-containing heterocyclic compounds (II). These penicillins were tested for in vitro activity against S. aureus, E. coli, K. pneumoniae, P. mirabilis, and P. aeruginosa. The 7-chloro-4-hydroxyquinoline derivative (23) and the 4-hydroxy-1, 5-naphthyridine derivatives (29-31, 33) were found to have potent antibacterial activity against E. coli, K. pneumoniae, P. mirabilis, and P. aeruginosa.