Studies on pyridonecarboxylic acids. III. Synthesis and antibacterial activity evaluation of 1,8-disubstituted 6-fluoro-4-oxo-7-piperazinyl-4H-[1,3]thiazeto[3,2- a]quinoline-3-carboxylic acid derivatives

Chem Pharm Bull (Tokyo). 1995 Jan;43(1):63-70. doi: 10.1248/cpb.43.63.

Abstract

A series of 1,8-disubstituted 6-fluoro-4-oxo-7-piperazinyl-4H-[1,3]thiazeto[3,2-a]quinoline-3- carboxylic acid derivatives was prepared and evaluated for antibacterial activity. In the 7-piperazinyl series, addition of a fluorine at C-8, which increased the in vitro activity for the 1-hydrogen and 1-methyl analogues and decreased it for the 1-phenyl analogue, improved the in vivo activity of all the analogues. Introduction of a methoxy group at C-8 of the 1-methyl-7-piperazinyl analogue also improved its in vivo antibacterial activity. The effect of 8-substituents on the in vitro and in vivo antibacterial activity of the 1-methyl-7-(4-methyl-1-piperazinyl) series is also discussed.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Bacterial Infections / drug therapy
  • Bacterial Infections / microbiology
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Male
  • Mice
  • Microbial Sensitivity Tests
  • Pyridones / chemistry*

Substances

  • Anti-Bacterial Agents
  • Carboxylic Acids
  • Pyridones