New quinolone antibacterial agents. Synthesis and biological activity of 7-(3,3- or 3,4-disubstituted-1-pyrrolidinyl)quinoline-3-carboxylic acids

J Med Chem. 1990 Feb;33(2):849-54. doi: 10.1021/jm00164a060.

Abstract

A series of 7-(3-amino- or 3-aminomethyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-o xo-3-quinolinecarboxylic acids was synthesized and tested for antibacterial activity. Unique to these quinolones was the presence of a methyl or phenyl group in the pyrrolidine ring. Although the in vitro activity of these agents was usually equal to or less than that of their unsubstituted counterparts, one quinolone, 7-[3-(aminomethyl)-3-methyl-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1 ,4-dihydro-4-oxo-3-quinolinecarboxylic acid, displayed exceptional potency both in vitro and in vivo, particularly against Gram-positive organisms.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Bacterial Infections / drug therapy
  • Chemical Phenomena
  • Chemistry, Physical
  • Magnetic Resonance Spectroscopy
  • Mice
  • Microbial Sensitivity Tests
  • Quinolones / chemical synthesis*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Quinolones