Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives.
A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr(3) in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production.
College of Pharmacy, Kangwon National University, Chunchon 200-701, South Korea.
Tran Thanh
TT
Dao
Yeon Sook
YS
Chi
Jeongsoo
J
Kim
Hyun Pyo
HP
Kim
Sanghee
S
Kim
Haeil
H
Park
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology; D002384:Catalysis / Q000187:drug effects; D002460:Cell Line; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D005419:Flavonoids / Q000138:chemical synthesis / Q000494:pharmacology*; D007527:Isoenzymes / Q000037:antagonists & inhibitors* / Q000378:metabolism; D051379:Mice; D011448:Prostaglandin Antagonists / Q000138:chemical synthesis / Q000494:pharmacology*; D011451:Prostaglandin-Endoperoxide Synthases / Q000378:metabolism; D011453:Prostaglandins / Q000096:biosynthesis*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D005419:Flavonoids; D007527:Isoenzymes; D011448:Prostaglandin Antagonists; D011453:Prostaglandins; C043561:chrysin; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases