Design And Synthesis Of Biscarboline Catalysts And Study Of Their Asymmetric Catalytic Activity And Antitumor Activity Of Correspounding Products

Chiral molecules widely distribute in nature and play an important and unique role in life. Chiral drugs cause wide attentions because of their different biological effects. It has a great significance to develope chiral catalysts with high enantioselectivity and high activity. In this study,L- tryptophan was used as a major starting material for synthesis of axial chiral biscarboline N-O catalysts. We studied their applications in enantioselective allylation of trichlorohydrosililane to bulky substituted aldehydes. Initially,the compounds involved in the study were well used in the cytotoxicity of examinations.Chapter one is the research review of asymmetric allylation of aldehydes mediated by Lewis acids and catalyzed by Lewis bases.In chapter two,we explored the axial chiral biscarboline-N, N′-dioxide catalysts with ester moiety on C-3,C-3′. Several axial chiral catalysts were obtained as enantiomerically purity. Twelve bulky substituted carboline aldehydes were synthesized from L-tryptophan.We studied enantioselective of all the axial chiral bicarboline-N, N′-dioxid catalysts in the addition of trichlorohydrosililane to the aldehydes.The results showed that the reaction could be successfully accomplished in 16 h at 25℃, leading to the corresponding chiral alcohol in high yields and ee% values. The best catalyst can achieve an enantioselectivity as high as 96%. we’ve got 80 new compounds.In chapter three,we studied the stereochemistry of the catalyst and the chiral alcohol by comparison of calculated and experimental VCD,ECD andOR,respectively.In chapter four, new carboline derivatives obtained from L-tryptophan were used for screen of cytotoxic activity against five human cancer cell lines in vitro by MTT assay. Some of them exhibited potential uses in future time. Productions of chiral catalysis have significant difference of cytotoxic activity(p<0.05).We studied the structure-function relationship.