Synthesis and PGE2 inhibitory activity of 5,7-dihydroxyflavones and their O-methylated flavone analogs.
5,7-Dihydroxyflavones and their O-methylated flavone analogs were prepared and evaluated their anti-inflammatory activity to decipher the structure-activity relationships. Most of the analogs were achieved from 2,4,6-trihydroxyacetophenone in 4 steps. 5,7-Dihydroxy-4'-methoxyflavone (4c) and 7-hydroxy-4',5-dimethoxyflavone (6c) were prepared following a different synthetic pathway. Among the synthetic flavones tested, 5-hydroxy-7-methoxyflavone analogs (3a-3e) showed moderate inhibitory activities of PGE2 production from LPS-induced RAW 264.7 cells.
Dao
Tran Thanh
TT
College of Pharmacy, Kangwon National University, Chunchon 200-701, Korea.
Chi
Yeon Sook
YS
Kim
Jeongsoo
J
Kim
Hyun Pyo
HP
Kim
Sanghee
S
Park
Haeil
H
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D016861:Cyclooxygenase Inhibitors / Q000494:pharmacology; D015232:Dinoprostone / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D005419:Flavonoids / Q000138:chemical synthesis* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008745:Methylation; D013329:Structure-Activity Relationship
D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D005419:Flavonoids; D008070:Lipopolysaccharides; C043561:chrysin; D015232:Dinoprostone