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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.

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Synthesis and Inhibitory Activity Against COX-2 Catalyzed Prostaglandin Production of Chrysin Derivatives. -A variety of chrysin derivatives such as (VII) are synthesized starting from 2-hydroxyacetophenone derivatives and evaluated for their inhibitory activities of COX-2 catalyzed prostaglandin production. Chrysin derivatives having a 3,4-dichlorophenyl substituent exhibit good inhibitory activity. -(DAO, T. T.; CHI, Y. S.; KIM, J.; KIM, H. P.; KIM, S.; PARK*, H.; Bioorg. Med.