PMID: 2104934Jan 1, 1990Paper

Synthesis and structure-activity relationships of new 7-[3-(fluoromethyl)piperazinyl]- and -(fluorohomopiperazinyl)quinolone antibacterials

Journal of Medicinal Chemistry
C B ZieglerY I Lin

Abstract

Some novel 6-fluoro-7-substituted-1,4-dihydro-4-oxoquinoline-3-carboxylic acids have been prepared. At the N-1 position "standard" substitution was employed with the ethyl, cyclopropyl, and p-fluorophenyl groups being used. At C-7 the introduction of some novel piperazines was made. Most notably, 2-(fluoromethyl)piperazine (10) and hexahydro-6-fluoro-1H-1,4-diazepine (16, fluorohomopiperazine) at the quinolone C-7 position produced products with similar in vitro antibacterial activity as the ciprofloxacin reference. The in vivo efficacy of 1-cyclopropyl-6-fluoro-7-[3-(fluoromethyl)piperazinyl]-1,4-dihydro-4- oxoquinoline-3-carboxylic acid (20) was excellent with better oral absorption than ciprofloxacin (2).

Citations

Apr 27, 2002·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Miguel Angel Cabrera PérezMarival Bermejo Sanz
Sep 6, 2003·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Miguel Angel Cabrera PérezMarival Bermejo Sanz
Jun 27, 2014·Organic & Biomolecular Chemistry·Sanghye ShinSungwoo Hong
Sep 26, 1997·Antimicrobial Agents and Chemotherapy·E EscribanoJ Moreno
Jan 21, 2011·ACS Combinatorial Science·Qi-Lun LiuYong-Ming Zhu

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