Fluoronaphthyridines and -quinolines as Antibacterial Agents. 5. Synthesis and Antimicrobial Activity of Chiral 1-tert-Butyl-6-fluoro-7-substituted-naphthyridones

Article abstract of DOI:10.1021/jm00100a028

A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared.These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position.In this paper we report the full details of the asymmetric synthesis of this series of compounds.Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity.Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.