Synthesis And Characterization Of Indolo Quinazoline Derivatives

Tryptanthrine is a kind of indoloquinazoline alkaloids, it exists in strobilanthescusia,chinese indigo, woad and some other plants which can prodece blue dyestuff, however, the contens of them are low. The structure and pharmacological activity of tryptanthrine receive much concern at present, and it is confirmed that the tryptanthrine has great biological activity of antibacterial,antiinflammatory,antitumor,antifungal and antiparasitic. As a medicinal resources, the ryptanthrine is outstanding, because the pharmacological action is wide, and the cytotoxicity is low, so the prospect of developing tryptanthrine as new drugs is worthy to study on. Tryptanthrine has natural bioactivity, but the plant material is limited. In addition, the research of synthetic tryptanthrine is less, so how to synthetise it and its derivatives to makes it has higher biological activity is a key of research in the future work.The compounds of oxime ethers and oxime esters have good biological activity in the aspect of antibacterial and antiviral, so they are widely applied in the medicine and pesticides, and it is always chosed as active group in the design of new drugs.In this paper, we designed and synthesized series of indoloquinazoline derivatives which have the biological activity. The main research work consists of two parts. In the first part, isatin derivatives were prepared by the reaction of condensation and cyclization with aniline derivatives, followed by condensation with isatoic anhydride to give tryptanthrine derivatives. The products 6-indolo quinazoline oxime ethers(esters) were prepared by oximatio,esterification and Williamson reactions. With the elemental analysis,1HNMR, MS and IR techniques, the structures of the compounds were characterized and determined.In the second part, the method of plate inhibition zone was used to detect the antibacterial activity of the target product. The results showed that when the concentration of drugs are lmg/mL, most of the intermediates and the final products exhibit good antibacterial effect, especially the gram-positive bacteria. The oxime ether(ester) group at C-6 position have significant effect on the biological activity, so it is the absolutely necessary active center. The antibacterial activities of the products are lowest, on the condition that the strong electron attracting group is at C-8 position, while the chloro-substituted products exhibit higher antibacterial activities than the others.