Studies On The Synthesis Of Natural Isoflavones And Their Mannich Base Derivatives

Genistein(Genistein),mainly found in legumes,is a natural soybean isoflavone which has a variety of biological activities.It has a weak estrogen activity,antioxidant activity and antifungal activity,for liver cancer,colon cancer,lung cancer,gastric cancer and prostate cancer and other diseases have a positive role in the prevention and treatment.Because the finches have little or no absorption in the gut,they limit its clinical application.Therefore,in order to get highly active substances has practical application value,this paper first synthesizes Genistein,and then uses it as a substrate to synthesize other natural products and Mannich bases derivatives.1?Genistein is used to catalyze pyrogallol acylation at room temperature by using BF3·Et2O as a catalyst with cheap pyrogallol and p-hydroxyphenylacetic acid as raw materials,and then drying the intermediate thereof,N,N-dimethylformamide(DMF),PCl5 and BF3·Et2O,the carbon closed-loop reaction and obtained.2?The natural product compound 2(Prunetin)and compound 3 is genetein as raw material,the use of acetone dissolved,into the appropriate proportion of sodium carbonate,dimethyl sulfate prepared,in addition,also has a biological activity of the compound 4.The intermediate 5 was prepared by reaction of natural product 3 with isopentenyl bromide,which was then subjected to Claisen rearrangement to give compound 6 and compound 7.Compound 8 is obtained by closing the hydroxyl group at the 5-position of compound 7 and the adjacent carbon-carbon double bond.The compounds 5,7and 8 were new compounds.3?The Mannich reaction was carried out by the natural product compound 3,which was modified by amine methylation in C6 positions of isoflavones and was synthesized from 8 non-reviewed isoflavones mannichbase derivatives 9?16.4?All of the synthesized compounds 1?16 have been confirmed by 1H NMR,13C NMR and MS.