Synthesis of novel 5-fluoro analogs of norfloxacin and ciprofloxacin

Journal of Medicinal Chemistry
1989.0

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.

Knowledge Graph

Similar Paper

Synthesis of novel 5-fluoro analogs of norfloxacin and ciprofloxacin
Journal of Medicinal Chemistry 1989.0
Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships
Journal of Medicinal Chemistry 1984.0
Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives
Journal of Medicinal Chemistry 1989.0
7-Substituted 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids: synthesis and biological activity of a new class of quinolone antibacterials
Journal of Medicinal Chemistry 1988.0
Synthesis and structure-activity relationships of new 7-[3-(fluoromethyl)piperazinyl]- and -(fluorohomopiperazinyl)quinolone antibacterials
Journal of Medicinal Chemistry 1990.0
Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents
Journal of Medicinal Chemistry 1985.0
Synthesis and biological activity of 5-alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic acids
Journal of Medicinal Chemistry 1991.0
Novel 5-amino-6-methylquinolone antibacterials: A new class of non-6-fluoroquinolones
Bioorganic & Medicinal Chemistry Letters 1997.0
Pyridonecarboxylic acids as antibacterial agents. Part 14. Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency
Journal of Medicinal Chemistry 1990.0
Synthesis and structure-activity relationship of 1-aryl-6,8-difluoroquinolone antibacterial agents
Journal of Medicinal Chemistry 1987.0