TOTAL SYNTHESIS OF 6,8-PRENYLACACETIN AND 8-PRENYLACACETIN AND CYTOTOXIC ACTIVITIES ON HELA CANCER CELL LINES IN HUMANS

Abstract

The first total synthesis of natural prenylated flavonoids of 6,8-prenylacacetin (1) and 8- prenylacacetin (2) were achieved through two different paths. The first road has passed the reaction: Chemoselective benzyl bromide at positions C-3 và C-5 of 2,4,6-trihydroxyacetophenone, BakerVenkataraman reaction, deprotection, the last step alkylation. The second road through: methoxymethyl protection, aldol condensation, cyclization, deprotection and alkylation. The overall yields of 1 và 2 were 25% and 27%, respectively. Their cytotoxic potential against Hela human cancer cell line was evaluated by the stvàard MTT assay. The results showed that most of the target compounds exhibited moderate to potent cytotoxicity against cancer cells comparable with the positive control cis-Platin. Compounds 1 and 2 showed selective cytotoxicity against Hela cells respectively, they are potential and selective anticancer agent and worthy of further development. All the synthesized compounds were confirmed by 1H-NMR, 13C-NMR và MS techniques. The synthesis process of 1 and 2 were via alkylation as a key step.