Dual-action cephalosporins incorporating a 3'-tertiary-amine-linked quinolone

J Med Chem. 1994 Feb 4;37(3):400-7. doi: 10.1021/jm00029a012.

Abstract

We have previously reported that linking quinolones to the cephalosporin 3'-position through an ester bond, a carbamate function, or a bond through a quaternary nitrogen produced cephalosporins with a dual mode of antibacterial action. We now describe a new class of dual-action cephalosporins, with greater chemical stability than those previously reported, in which the basic nitrogen of ciprofloxacin is bonded directly to the 3'-cephalosporin position, i.e., the two moieties are linked through a tertiary amine function. These compounds have demonstrated potent activity against a broad spectrum of Gram-positive and Gram-negative bacteria, including beta-lactam-resistant strains.

Publication types

  • Comparative Study

MeSH terms

  • Cephalosporins / chemistry*
  • Cephalosporins / metabolism
  • Cephalosporins / pharmacology*
  • Chromatography, High Pressure Liquid
  • Ciprofloxacin / chemistry
  • Drug Resistance, Microbial
  • Drug Stability
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Molecular Structure
  • Nitrogen / chemistry
  • Quinolines / chemistry*
  • Structure-Activity Relationship
  • beta-Lactamases / metabolism

Substances

  • Cephalosporins
  • Quinolines
  • Ciprofloxacin
  • quinoline
  • beta-Lactamases
  • Nitrogen