Synthesis And Antitumor Activity Of Chrysin Containing Triazoles Derivatives

The chrysin is a flavonoid compound which extracted from the wood butterfly of the genus Dictyophora.It is also known as 5,7-dihydroxyflavone,because the 5-position and the 7-position have a hydroxyl group.It has a wide range of biological activity,antioxidant,antiviral,anti-allergy,anti-inflammatory,anti-anxiety and anti-tumor.Anti-tumor activity,especially is a hot spot in today’s research.However,the structure determines that chrysin is an amphoteric compound,and its water solubility and fat solubility are very low,which limit its’ chemical efficiency.The research showed that the 5 hydroxyl and 7 hydroxyl groups in the chrysanthemum molecule would react and lose their activity,the structural modification of these two loci could improve their solubility and pharmacokinetic properties,improve their metabolic stability And bioavailability.The triazole structure has the good biological activity of the nitrogen-containing heterocyclic compounds,and the introduction of the matrix molecules can change the solubility and pharmacokinetic properties of the maternal molecules and enhance the biological activity of the parent molecules.In this paper,seven hydroxyl groups were compound with nitrogen-containing heterocyclic rings on the parent of the chrysanthemum,and eight 7-((3-substituted benzyl-triazol-4-yl-3H-1,2,3-)methoxy)-5-hydroxy-2-phenyl-4H-benzopyran-4-one derivatives and eleven 5-hydroxy-2-substituted phenyl-7-((4-phenyl-4H-1,2,4-triazol-3-yl)-methoxy)-4H-benzopyran derivatives were synthesized.The product was isolated and purified by silica gel column chromatography.The product was characterized by MS,1H NMR,and 13C NMR.The antitumor activity of 19 derivatives was compared by suing MTT assay.Comparing to the Chrysin,the inhibition of BEL-7402 tumor cells was significantly enhanced by 9b,5e and 5h,and the inhibitory effect of 9d,9j and 9k on HEPG-2 tumor cells was improved,and 5b and 5g on L-02 The inhibitory effect of 9a and 9i on SGC-7901 tumor cells was improved,and the inhibitory effect of 5g on A549 tumor cells was improved.The inhibitory effect of 5g on MGC-803 tumor cells was higher than that in the control group,and the anti-tumor activity was 51%higher than that in the control group and the IC50 value was 5.92.It was suggested that the 7-hydroxyl group of the chrysin could be used to selectively improve the antitumor activity of the chrysanthemum.