Research On Synthesis Of Resveratrol Analogues And Their Biological Properties

Nineteen new resveratrol analoges were designed and synthesized. Compounds(1) were synthesized from 3,5-dimethoxy-benzylbromine as the starting material via the Witting-Hornor reaction;Vilsmeier formylation of compounds(1) by treatment with POCl3 and DMF yielded aldehydes(4),followed reduction by NaBH4 and compounds(6) were obtained;condensation reaction of compounds(4) with amin and hydrazine afforded compounds(5),which were shiff base or hydrazine compounds, followed reduction by NaBH4 and compounds(7) were obtained;3,5-dimethoxybenzyl cyanide was synthesized from 3,5-dimethoxybenzyl bromide and sodium cyanide, compound was obtained via Knoevenagel reaction by 3,5-dimethoxybenzyl cyanide and 2,6-dichlorbenzaldehyde; (1c) and (8) were transformed into compounds(2) and (9) via demethylation by boron bormide/dichloromethane;compound(3) was synthesised from compound(2)and iodine in methanol.The structures of the products of every step reaction were charaterized by IR,1H-NMR,MS spectra,elmentory analysis and the results all agree with the structure of compounds.Compounds were tested in vitro for their anti-tumor activity on liver tumor cells BEL-7402 and their toxicity on normal liver cells L02.Their IC50 values were calculated. The results showed that 5a,5b and 5c had better anti-tumor activity and lower toxicity,their IC50 to BEL-7402 are 22.27,23.83 and 20.70μmol/L,and IC50 to L02 are 84.82,90.97 and 131.92μmol/L respectively.They seem to be the better anti-tumor leader compounds.Based on the characteristics of parameters of target compounds,connecting with their biological activities dates tested, the simple structure-activity relationships were studied.