Synthesis and antitumor activity of novel chrysin derivatives

Chrysin was synthesized in five steps starting from 2,4,6-trihydroxyacetophenone via methylation,acylation,Baker-Venkataraman rearrangement,cyclization and deprotection.With chrysin as the lead compound,novel chrysin derivatives 8a-8u were designed and synthesized.The chemical structures of these compounds were confirmed by 1H NMR,13C NMR,IR and MS.Twenty-one new chrysin derivatives were prepared and their antitumor activities were evaluated by MTT method on HCT-116(human colon cancer cell line),HeLa(human cervical carcinoma cell line),DU-145(human prostate cell line),SGC-7901(human gastric cancer cell line),and HEK-293(human embryonic kidney cell line).Among these derivatives,5-hydroxy-2-phenyl-7-(2-(piperazin-1-yl)ethoxy)-4H-chromen-4-one(8o)had the most potent antitumor activity against HCT-116,HeLa,DU-145,and SGC-7901 cells.