Pyridonecarboxylic acids as antibacterial agents. 4. Synthesis and antibacterial activity of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo*-1,8- naphthyridine-3-carboxylic acid and its analogues

Article abstract of DOI:10.1021/jm00378a004

The title compounds with an amino- and/or hydroxy-substituted cyclic amino group at C-7 were prepared with 1-substituted 7-chloro-, 7-(ethylsulfonyl)-, and 7-(tosyloxy)-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acids and their ethyl esters with cyclic amines such as 3-aminopyrrolidine. The N-1 substituent includes ethyl, vinyl, and 2-fluoroethyl groups. As a result of in vitro and in vivo antibacterial screenings, three compounds, 1-ethyl- and 1-vinyl-7-(3-amino-1-pyrrolidine)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyri dine-3-carboxylic acids and 1-vinyl-7-[3-(methylamino)-1-pyrrolidinyl] analogue, were found to be more active than enoxacin and to be worthy of further biological study. Structure-activity relationships are discussed.