Synthesis And Medicinal Property Study Of Functional1,2,3-triazole Derivatives

1,2,3-Triazoles, isoxazole derivatives and organoselenium compounds have widelyused in industrial applications such as organic synthesis, medicine and materials due to itsuseful pharmaceutical and biological activity.1,2,3-Triazoles and isoxazoles possessexcellent biological activities such as anti-HIV activity, antimicrobial activity andanti-inflammatory. Organoselenium compounds are closed related to human health becauseof their perfect anti-cancer effect, inhibition of cardiovascular disease and increaseimmunity. If different pharmacodynamic structures were unified into a class of compounds,which will have better curative effects on certain diseases. According to the above ideas,1,2,3-triazoles which include isoxazole derivatives and organoselenium were designed andsynthesized on the basis of previous, preliminary study of the performance of theirpharmaceutical activity. Therefore, the research of this paper has important theoreticalsignificance and practical value. The research contents of this paper are as follows:Firstly, based on the synthesis of single or double azides and alkynes, treatment ofazides with isoxazole alkynes led to the formation of kinds of1,2,3-triazoles.4-chloroisoxazole alkyne and4-benzyl chloride azide as raw materials, the synthesis of5-(((1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl) methoxy) methyl)-3-(4-chlorophenyl)isoxazole (3b) has been discussed via Huisgen-Click reaction. Effects of catalyst on theyield of3b were investigated, then using the optimum catalyst,10novel single1,2,3-triazoles have been synthetised successfully. At the same time,5novel double1,2,3-triazoles were obtained staring from isoxazole alkynes and2,2-bis(azidomethyl)propane-1,3-diol in37%-62%yields. Besides, the single crystal X-ray diffraction forcompound3h was tested and the crystal structure of the compound3h shows that3h isbelong to monoclinic space group.Secondly, benzyl chloride and selenium as raw materials, the synthesis of dibenzyldiselenides has been discussed under phase transfer conditions. Effects of catalyst, solventson the yields were investigated. Dibenzyl diselenides derivatives were prepared in63%–93%yields. To the best of our knowledge, only few reactions to obtain benzylpropargyl selenides were described so far. Herein, we explored a new method to synthesize2benzyl propargyl selenides in the66%yield by nucleophilic reactions of dibenzyl diselenides and3-bromo-1-propyne in present of Sodium borohydride as reducing agent.Benzyl propargyl selenides and benzyl azides as raw materials, a class of1,2,3-triazolescontaining selenium has been synthesized in the45%–71%yields via Huisgee-Clickreaction which made a foundation in the research of Organoselenium compounds.Thirdly, the influences between electron-withdrawing or donating and yields havebeen discussed. Moreover, the structures of all synthesized products were characterized byMS,1H and13C NMR, IR.At last, all the synthesized1,2,3-triazoles containing isoxazole ring or selenium havebeen tested for antimicrobial activity. The result showed that target compounds did notexhibit excepted antimicrobial activities when the concentration of target products was512ug/mL.In conclusion, we designed a novel structure that combine isoxazole ring withselenium respectively. The explorations of novel1,2,3-triazole synthesis methods andoptimal reaction conditions made a foundation in the fields of organic synthesis. Inaddition, the vitro antibacterial experiments about above-mentioned compounds haveshown the desired products do not have well antibacterial properties. However, theresearch on other aspects of the biological activity is still underway, and we expect theycould demonstrate good anti-inflammatory, anti-viral and anti-cancer cells properties.