[Synthesis and anti-inflammatory activity of quinopimaric acid derivatives].
Under the action of PCl(5), the Beckman rearrangement of a 3 : 1 mixture of Z- and E-ketoximes of 18beta-hydroxydihydroquinopimaric acid resulted in 5'-caprolactam and isomeric caprolactams containing fragments of cyclic ether. Z- and E-ketoximes were separated as acetates. Using a carrageenan inflammation model, we demonstrated that the anti-inflammatory activity of quinopimaric acid derivatives was comparable with that of diclofenac.
Institute of Organic Chemistry, Ufa Research Centre, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054 Russia. obf@anrb.ru
O B
OB
Kazakova
E V
EV
Tret'iakova
I E
IE
Smirnova
L V
LV
Spirikhin
G A
GA
Tolstikov
E V
EV
Chudov
G V
GV
Bazekin
A F
AF
Ismagilova
D045784:Abietanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002351:Carrageenan; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D009980:Influenza A virus / Q000187:drug effects; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D023382:Toxicity Tests, Acute
D045784:Abietanes; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000998:Antiviral Agents; C542630:dihydroquinopymaric acid; D002351:Carrageenan