Synthesis and bacterial DNA gyrase inhibitory properties of a spirocyclopropylquinolone derivative

J Med Chem. 1988 Sep;31(9):1694-7. doi: 10.1021/jm00117a005.

Abstract

A novel conformationally restricted 1-cyclopropylquinolone (1) that incorporates structural features of both ofloxacin and ciprofloxacin has been prepared. Compound 1 was found to be a DNA gyrase inhibitor having potency similar to ofloxacin but less than ciprofloxacin. The cellular inhibitory and in vivo antibacterial potencies of 1 were found to be less than those of the two reference agents.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Bacteroides / enzymology
  • Chemical Phenomena
  • Chemistry
  • Ciprofloxacin / pharmacology
  • Escherichia coli / enzymology
  • Mice
  • Ofloxacin
  • Oxazines / chemical synthesis
  • Oxazines / pharmacology*
  • Pseudomonas aeruginosa / enzymology
  • Staphylococcus aureus / enzymology
  • Streptococcus / enzymology
  • Topoisomerase II Inhibitors*

Substances

  • Oxazines
  • Topoisomerase II Inhibitors
  • 9'-fluoro-10'-(4-methyl-1-piperazinyl)-7'-oxospiro(cyclopropane-1,3'(2'H)-(7H)pyrido(1,2,3-de)(1,4)benzoxazine)-6'-carboxylic acid
  • Ciprofloxacin
  • Ofloxacin