Synthesis Of Phenanthrene And Carbazole Derivatives Based On Cyclic Iodonium、Strutural Characterization And Their Anticancer Efficacy Study

Recently, Linear diphenyliodoniums, as arylating reagents, have been widely used in arylation to construct C-C bonds and C-N bonds due to its excellent reactivities. However, after arylation, the iodobenzenes produced from linear iodoniums are not utilized and discarded as wastes, which reduces the reaction atom economy.Compared to linear diphenyliodoniums, the iodoarene generated from diphenyliodonium after arylation remains as a part of the arylated product, which can be furtherly utilized to construct another constitutions with another regents. In terms of atom economy, cyclic diphenyliodoniums are advantageous when using as arylating reagents. In this paper, we synthesized a series phenanthrenes and carbazoles with palladium catalyzed inter-molecular arylation. Furtherly, our synthetic dibenzocarbazoles have been studied as anti-tumor reagents.In the second chapter, we developed a palladium catalyzed [4+2] cyclization of cyclic diphenyliodoniums and alkynes to synthsis 9-ethyl-10-phenylphenanthrene. Next, the effect of palladium catalysts, addtions, solvents and ligands were investigated. At last,, an optimized reaction condition, Pd(OAc)2/PCy3/Zn/DCE, were obtained. Base on the conditions, about 20 compounds were synthesized, and the subsituent effect were investigated.In the third chapter, we developed a palladium catalyzed C-H functionalization of indoles and cyclic diphenyliodoniums to synthesize 9-ethyl-9H-dibenzo[a,c]carbazoles. Next, the effect of palladium catalysts, base, and solvents were investigated. At last, an optimized reaction condition, Pd(OAc)2/Na2CO3/air/DCE, were obtained. Base on the conditions, about 20 compounds were synthesized, and the subsituent effect were investigated.In the forth chapter, all dibenzocarbazoles were investigated as anti-tumor reagents in biological evaluation assays including cell proliferation, cell clone, cell apoptosis and cell cycle studies. The experiment results showed that all dibenzocarbazoles may be protentianl antitumor reagents. Particular, HCT-116 cells, capan2 cells and JEKO-1 cells can be dramatically inhibited by methyl 9H-dibenzocarbazole-11-carboxylate. With low concentration, this compound can prevented the clone formation of HCT-116 cells and induced HCT-116 cells apoptosis. The results of cell cycle showed that HCT-116 cells was blocked in G2. All results showed that the compound may be a potential lead compound of antitumor drugs with its excellent antitumor activity.