RESUMEN
OBJECTIVE: To design and synthesize two kinds of allyl-substituted quercetin and investigate their anti-oxidation and anti-tumor activities in vitro. METHODS: The target compounds 1 and 2 were first synthesized from quercetin by hydroxyl protection, allylation,Claisen rearrangement and deprotection. The anti-oxidation and anti-tumor activities of the target compounds and intermediate products were evaluated by DPPH and MTT assay. RESULTS: Eight compounds were synthesized,including six intermediates and two target compounds,in which four were new compounds. All of them were confirmed by 1H-NMR,13C-NMR and LC-MS spectra. The anti-oxidation and anti-tumor tests showed that compounds 1,2,5,6,8 and 9 had anti-oxidation activities and compound 5 inhibited A549 lung cancer cell proliferation. Compound 9 could inhibit the proliferation of lung cancer A549 cells and HepG2 cells. CONCLUSION: The compounds with electron-donating groups have significant anti-oxidant activity. When acetyl and methyl ether groups are used as the protecting groups,the position of introducing allyl group to quercetin has obvious impact on the anti-tumor activity.