Studies on β-Lactam Antibiotics for Medicinal Purpose. II. Synthesis of D (-)-α-[Dioxo-1-piperazinecarboxamido] benzylpenicillins and Structure-Antibacterial Activity

Abstract
D(-)-.alpha.-(4-Substituted 2,3-dioxo-1-piperazinecarboxamido)benzylpenicillin (I), D(-)-.alpha.-(4-substituted 2,5-dioxo-1-piperazinecarboxamido)benzylpenicillin (II) and D(-)-.alpha.-(4-substituted 3,5-dioxo-1-piperazinecarboxamido)benzylpenicillin (III) were prepared. These compounds showed in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Proteus vulgaris, Klebsiella pneumoniae and Serratia marcescens, the activity being in the order of I > II, III. These compounds had a stronger antibacterial activity against gram-negative bacilli than aminobenzylpenicillin or carbenicillin.

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