title: Synthesis and PGE2 inhibitory activity of 5,7-dihydroxyflavones and their O-methylated flavone analogs.
abstract: 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.
authors.affiliation: College of Pharmacy, Kangwon National University, Chunchon 200-701, Korea.
authors.forename: Tran Thanh
authors.initials: TT
authors.lastname: Dao
authors.forename: Yeon Sook
authors.initials: YS
authors.lastname: Chi
authors.forename: Jeongsoo
authors.initials: J
authors.lastname: Kim
authors.forename: Hyun Pyo
authors.initials: HP
authors.lastname: Kim
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Haeil
authors.initials: H
authors.lastname: Park
mesh_terms: 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
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D005419:Flavonoids; D008070:Lipopolysaccharides; C043561:chrysin; D015232:Dinoprostone