Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationships of new 1-substituted derivatives.
A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.
Bouzard
D
D
Centre de Recherche Bristol-Myers, Torcy, France.
Di Cesare
P
P
Essiz
M
M
Jacquet
J P
JP
Remuzon
P
P
Weber
A
A
Oki
T
T
Masuyoshi
M
M
D042462:4-Quinolones; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004285:Dogs; D006090:Gram-Negative Bacteria / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013210:Staphylococcus / Q000187:drug effects; D013329:Structure-Activity Relationship
D042462:4-Quinolones; D000900:Anti-Bacterial Agents; D009287:Naphthyridines