Synthesis And Study On The Activity Of Chiral 2,3-Epoxy Alcohol Derivatives

Objective: based on the Sharpless asymmetric epoxidation of allyl alcohol,we screene and establish the 2-pentyl-3-phenyl allylic alcohol asymmetric epoxidation conditions. In order to obtain different chiral 2,3- epoxy alcohol derivatives.The optimum epoxidation conditions were applied to its analogues and allyl alcohol with alkynyl. Explore antitumor activity of these compounds.Methods:investigate the effects of the type of catalyst,the amount of catalyst, reaction temperature and the type of molecular sieve on the 2,3-epoxy alcohol,s yield and enantiomeric excess value(ee) of the 2-pentyl-3-phenyl allylic alcohol asymmetric epoxidation product and selecte the reaction conditions which can improve yield and ee value of 2,3-epoxy alcohol.(R)-2-pentyl-3-phenyl-2, 3-epoxy alcohol,(R)-3-phenyl-2,3-epoxy alcohol,(R)-2-methyl-3-phenyl-2,3-epoxy alcohol on the human cervical carcinoma He La cells inhibition were detected by CCK8. Results:tetraisopropyl titanate(Ti(OiPr) 4)-diisopropyl L-tartrate((L)-(+)-DIPT)as catalyst system, n(Ti(OiPr) 4): n((L)-(+)-DIPT) = 0.65, 4? molecular sieve powder, reaction tempera- ture is-25 ?, reaction time is 4 hours,the chiral epoxy alcohol,s yield up to 98% and ee value up to 92%,the same conditions can be applied to its analogues of the asymmetric epoxidation reaction.(R)-3-phenyl-2,3-epoxy alcohol,(R)-2-methyl-3-phenyl-2,3-epoxy alcohol have no inhibitory effect on the human cervical carcinoma He La cells, only the(R)-2-pent- yl-3-phenyl-2,3-epoxy alcohol have inhibitory effect on the human cervical carcinoma He La cells. Conclusions:establish the 2-pentyl-3-phenyl allylic alcohol Sharpless asymmetric epoxidation conditions which can be used to its analogues to synthesize the chiral 2,3- epoxy alcohol derivatives with high yield and ee value.(R)-3-phenyl-2,3-epoxy alcohol,(R)-2-methyl-3-phenyl-2,3-epoxy alcohol have no inhibiting effect on the human cervical carcinoma He La cells,only the(R)-2-pentyl-3-phenyl-2,3-epoxy alcohol have inhibitory effect on the human cervical carcinoma He La cells, and displayed a marked concentration-effect relationship.