title: Synthesis of novel 5-fluoro analogues of norfloxacin and ciprofloxacin.
abstract: A series of polyfluoro-3-quinolonecarboxylic acids have been synthesized and their in vitro antibacterial activity evaluated. The desired 7-(substituted amino) derivatives were prepared from the 5,6,7,8-tetrafluoroquinolone acids. Conversely, amine displacement occurred primarily at the 5-position when the ester was used. Structure-activity studies indicated that the antibacterial activity was greatest when the N-1 substituent was cyclopropyl and the 7-substituent was 4-methyl-1-piperazinyl. All 5-(substituted amino) derivatives showed poor in vitro activity.
authors.affiliation: American Cyanamid Company, Lederle Laboratories, Pearl River, New York 10965.
authors.forename: D B
authors.initials: DB
authors.lastname: Moran
authors.forename: C B
authors.initials: CB
authors.lastname: Ziegler
authors.forename: T S
authors.initials: TS
authors.lastname: Dunne
authors.forename: N A
authors.initials: NA
authors.lastname: Kuck
authors.forename: Y I
authors.initials: YI
authors.lastname: Lin
mesh_terms: D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002939:Ciprofloxacin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004754:Enterobacter / Q000187:drug effects; D013293:Enterococcus faecalis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D004927:Escherichia coli Infections / Q000188:drug therapy; D007711:Klebsiella pneumoniae / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009643:Norfloxacin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012706:Serratia marcescens / Q000187:drug effects; D013203:Staphylococcal Infections / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D002939:Ciprofloxacin; D009643:Norfloxacin