PMID: 8464033Apr 2, 1993Paper

7-Azetidinylquinolones as antibacterial agents. Synthesis and structure-activity relationships

Journal of Medicinal Chemistry
J FrigolaE Valentí

Abstract

A series of novel antibacterial quinolones and naphthyridones has been prepared which contain 7-azetidinyl substituents in place of the usual piperazine or aminopyrrolidine groups. These azetidinyl derivatives were evaluated for in vitro activity by determining minimum inhibitory concentrations against a variety of bacteria. In vivo efficacy in the mouse infection model and blood levels in the mouse were determined for several compounds. The influence on the structure-activity relationships of varying substituents in the azetidine ring and at position 8 (CH, CF, CCl, N) and N-1 (ethyl, fluoroethyl, cyclopropyl, tert-butyl, 4-fluorophenyl, and 2,4-difluorophenyl) was also studied. Compounds with outstandingly broad-spectrum activity, particularly against Gram-positive organisms, improved in vivo efficacy, and high blood levels were identified in this work. 7-Azetidinyl-8-chloroquinolones were considered as warranting further development.

Citations

Mar 4, 2008·Chemical & Pharmaceutical Bulletin·Yoshifumi IkeeYoshimitsu Nagao
Nov 10, 2015·Archiv der Pharmazie·Alka MadaanManu Jaggi
Jan 10, 2002·Chemical Reviews·Yves DejaegherNorbert De Kimpe
Jan 1, 1996·Antimicrobial Agents and Chemotherapy·R CollJ Guinea
Oct 1, 2010·Organic Letters·Antonio FeulaJohn S Fossey
Sep 26, 2006·The Journal of Organic Chemistry·Michael C Hillier, Cheng-yi Chen

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