Peroxide chemistry of triaryl-substituted imidazoles. Fenflumizole, a non-steroidal, anti-inflammatory agent

Acta Chem Scand (Cph). 1991 Jul;45(6):627-31. doi: 10.3891/acta.chem.scand.45-0627.

Abstract

Fenflumizole, [2-(2,4-difluorophenyl)4,5-bis(4-methoxyphenyl)imidazole] is a nonsteroidal, anti-inflammatory analgesic. It reacts quantitatively with 1O2 forming 2-(2,4-difluorophenyl)-4-hydroperoxy-4,5-bis(4-methoxyphenyl)imidazole in a reversible reaction. In ethanol solution at ambient temperatures, the peroxide regenerates parent fenflumizole and 1O2 together with minor quantities of other products. The structures of those products point to the intermediacy of a 1,3-endoperoxide and a dioxetane. These observations may be relevant to the biological activity of fenflumizole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Hydrolysis
  • Imidazoles / chemistry*
  • Molecular Structure
  • Peroxides
  • Spectrophotometry
  • Thermodynamics

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Imidazoles
  • Peroxides
  • fenflumizole