Peroxide chemistry of triaryl-substituted imidazoles. Fenflumizole, a non-steroidal, anti-inflammatory agent.
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.
Frandsen
P L
PL
Animal Biotechnical Research Center, National Veterinary Laboratory, Copenhagen, Denmark.
Håkansson
K
K
Holm
A
A
Harrit
N
N
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D006868:Hydrolysis; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D010545:Peroxides; D013053:Spectrophotometry; D013816:Thermodynamics
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007093:Imidazoles; D010545:Peroxides; C038996:fenflumizole