Synthesis and structure-activity relationship of 1-aryl-6,8-difluoroquinolone antibacterial agents.
A series of new arylfluoroquinolones has been prepared. These derivatives are characterized by having fluorine atoms at the 6- and 8-positions, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. The in vitro antibacterial potency is greatest when the 1-substituent is 2,4-difluorophenyl and the 7-substituent is a 3-amino-1-pyrrolidinyl group. 1-(4-Fluorophenyl)-6,8-difluoro-7-piperazin-1-yl-1,4-dihydro-4-oxo quinoline-3- carboxylic acid (22) was found to possess excellent in vitro potency and in vivo efficacy.
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001424:Bacterial Infections / Q000188:drug therapy; D005260:Female; D005461:Fluorine / Q000494:pharmacology / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008826:Microbial Sensitivity Tests; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D011804:Quinolines; D005461:Fluorine