Synthesis Of C4'or C6 Bits Flavonoids Derivatives And Preliminary Study Of Their Biological Acticivies

1,2,3-triazole flavonoids derivatives and 1,2,3-triazolehesperidin derivatives were synthesized and their monoamine oxidase inhibitory activity were tested in this thesis.We got some flavonoids derivatives of good inhibitory activity.Starting from phenol with different substituent,the corresponding acetyl phenol esters were prepared by esterification,and then hydroxy acetophenones were got through Fires rearrangement.After which by aldehyde ketone condensation reaction with different substituent of benzaldehyde,followed by cycloaddition with iodine,flavonoids were synthesized.After bromination reaction with NBS,azide flavonoids were prepared by sodium azide.Finally,cycloaddition with terminal alkynes compounds containing amide bond,phenol and aniline,flavonoids contained 1,2,3-triazole were synthesized.The natural flavonoid hesperidin was chosen as the initial substrate to get the hesperidin by heating reflux reaction with sulfuric acid,and then reacted with propargyl bromide and allyl bromide under the effect of potassium carbonate to produce the corresponding hesperidins containing terminal alkynes and olefins,respectively.In the end,1,2,3-triazole flavonoids were synthesized through cycloaddition of hesperidins containing terminal alkynes and trinitride;hesperidin derivatives containing oxazoles were produced by cycloaddition of hesperidins containing terminal olefins and aromatic oximes.Monoamine oxidase inhibitory of 1,2,3-triazole flavonoids derivatives and 1,2,3-triazole hesperidin derivatives were tested by fluorescence probe method.The results show that 1,2,3-triazole derivatives containing aniline flavonoids a-4-3,b-4-3 and c-4-3 show significant inhibition to MAO-B(IC₅₀<10?M);1,2,3-triazole derivatives containing lipid hesperidin 1-5-1 show significant inhibition to MAO-B(IC_5O=1.2?M);1,2,3-triazole derivatives containing phenol flavonoids had no obvious inhibitory activity to MAO-A and MAO-B.They are all exhibit-high selectivity to MAO-B.In conclusion,triazoles avail to improve inhibitory activity of flavonoids,and flavonoids with electron-withdrawing groups?ester or fluorine base?display higher inhibitory activity to MAO.