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Synthesis And Application Research For Certain Indole Derivations

Posted on:2011-02-07Degree:MasterType:Thesis
Country:ChinaCandidate:C S ShenFull Text:PDF
GTID:2121360305954692Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
Indole derivatives widespread in nature, because of its unique chemical structure and biological activity, are widely used in medicine, spices, dyes and other industries. Therefore, the chemists were very concerned about the synthesis of indole derivatives, and more and more indole derivatives were extracted from the natural world or synthesized, which leeding the development of indole chemistry. In this paper, based on the synthesis of bis(indolyl)methane derivatives containing isoxazole ring and synthesis techniques of 5-nitro-indole, we carried out exploratory research.First, in the reseach of (3-phenylisoxazol-5-yl)methanol, we found that in the literature reported, the problem of synthesis of (3-phenylisoxazol-5-yl)methanol derivatives was long reaction time, low yield. Following with the research of synthesis isoxazole, we found ultrasonic method can greatly improve the yield of target products. Compared with the traditional methods, we noted that the synthesis of (3-phenylisoxazol-5-yl)methanol from aldoximes in one-pot synthesis under ultrasound can shorten 1-1.5h reaction time and enhance 15%-40% product yield under ultrasound.In the synthesis of bis(indolyl)methanes containing heterocyclic ring, we introduced isoxazole into bis(indolyl)methane system. (3-Phenylisoxazol-5-yl)met- hanol derivatives were oxidized and the produces reacted with indole. The bis(indolyl)methanes were synthesized through two methods. Based on the result, the ultrasound can aviod the environmental pollution, but the yield of the produce was lower than the method reported using TCT as catalyst in conventional stirring. We examined anti-cancer activity of bis(indolyl)methanes through the cell of MCF-7. It appeared that bis(indolyl)methanes had a good anti-tumor activity. Therefore, the bis(indolyl)methane compounds have the value of development and research.In addition, we carried out for the study on the synthesis techniques of 5-nitro-indole, because of the decline in the price of indole. In this paper, the time, temperature and pH for reaction were investigated, and the optimum conditions was determined, which is helpful for industrial production. The compounds were confired by the melting point, IR, NMR, and the purity of produce was determined over 95% by HPLC.In all, in the paper, through multi-step reaction, we synthesized 7 pairs of bis(indolyl)methanes containing isoxazole ring pharmacological properties and biological activity that has not been reported. In the reaction, we improved the method of synthesis for (3-phenylisoxazol-5-yl)methanols. Ultrasonic assisted synthesis can solve the problem of long reaction time, low yield. Finally, we took out reseach of Synthesis and process for 5-nitroindole. In the paper, we confirmed the high-point reaction condition. As...
Keywords/Search Tags:Bis(indolyl)methanes, 5-nitro-indole, Organic Synthesis, Isoxazole, Indole
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