Quinolone antibacterials: Preparation and activity of bridged bicyclic analogues of the C sub(7)-piperazine

A series of quinolone and naphthyridine antibacterial agents possessing as the C sub(7)-heterocycle bicyclic 2,5-diazabicyclo(n.2.m)alkanes, where n = 2, 3 and m = 1, 2, and a series including 4-aminopiperidine and 3-amino-8-azabicyclo(3.2.1)octanes have been prepared and evaluated in vitro and in v...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1991-01, Vol.34 (2), p.656-663
Main Authors: Kiely, J S, Hutt, M P, Culbertson, T P, Bucsh, R A, Worth, D F, Lesheski, LE, Gogliotti, R D, Sesnie, J C, Solomon, M, Mich, T F
Format: Article
Language:English
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Summary:A series of quinolone and naphthyridine antibacterial agents possessing as the C sub(7)-heterocycle bicyclic 2,5-diazabicyclo(n.2.m)alkanes, where n = 2, 3 and m = 1, 2, and a series including 4-aminopiperidine and 3-amino-8-azabicyclo(3.2.1)octanes have been prepared and evaluated in vitro and in vivo for antibacterial activity against a variety of Gram-negative and Gram-positive organisms. These compounds were also tested against the target enzyme bacterial DNA gyrase. All the examples investigated are nearly equipotent with the parent 7-piperazinyl analogues. Only endo-7-(3-amino-8-azabicyclo(3.2.1)oct-8-yl)-1-cyclopropyl-6,8-dif luoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid displays activity that surpasses that of the piperazine parent.
ISSN:0022-2623