Syntheses and anti-inflammatory activity of novel oximes and O-acyloximes.
Novel oximes were prepared from the corresponding aldehyde or ketone in the usual way, and a number of oxime esters, O-lauroyl, O-2-pyridinecarbonyl, O-nicotinoyl, and O-isonicotinoyl oximes were synthesized by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI)-4-dimethylaminopyridine (DMAP) method or a mixed anhydride method, in our search for potent anti-inflammatory compounds. The anti-inflammatory activity of these compounds was assessed by the carrageenan-induced paw edema assay in rats. The oximes (4, 5, and 13), O-lauroyloxime 1L, O-nicotinoyloximes (1N, 2N, 3N, and 4N), O-isonicotinoyloxime 1I, and O-2-pyridinecarbonyloxime 7P showed higher anti-inflammatory potency than aspirin, a prostaglandin cyclooxygenase inhibitor.
Katagi
T
T
Faculty of Pharmaceutical Sciences, Mukogawa University, Hyogo, Japan.
Kataoka
H
H
Takahashi
K
K
Fujioka
T
T
Kunitomo
M
M
Yamaguchi
Y
Y
Fujiwara
M
M
Inoi
T
T
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D010091:Oximes / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley
D000894:Anti-Inflammatory Agents, Non-Steroidal; D010091:Oximes