Synthesis and Biological Activity of Novel 1-Substituted Phenyl（glycosyl）-4-{4-[（4,6-dimethoxy）pyrimidin-2-yl] Piperazin-l-yl}methyl-lH-1,2,3-triazoles  

作　　者：MAO Ming-zhen LI Yu-xin ZHOU Yun-yun YANG Xiao-ping ZHANG Xiu-lan ZHANG Xiao LI Zheng-ming 

机构地区：[1]State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China [2]School of Pharmacy, University of Wyoming, Laramie WY 82071, USA

出　　处：《Chemical Research in Chinese Universities》2013年第5期900-905,共6页高等学校化学研究（英文版）

基　　金：Supported by the National Basic Research Program of China（No.2010CB126106）, the Fundamental Research Funds for the Central Universities and Natural Science Foundation of China（No.31000861）.

摘　　要：A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cyeloaddition between 4,6-dimethoxy-2-[（4-prop-2-ynyl）piperazin-l-yl]pyrimidine and each of different azides catalysed by in situ generated Cu（I）. The O-acyl protecting groups on glycosyl 1,2,3-triazoles were removed by triethylamine in wet methanol. Their chemical structures were established on the basis of corresponding tH NMR, 13C NMR, MS and elemental analysis. The fungicidal activities of target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Phytophthora capsici, Cercospora arachi- dicola and Gibberella zeae at 50 μg/mL. The bioassay results indicate that some of the compounds exhibited mode- rate but promising fungicidal activities. In particular, acetylated glucopyranosyl triazole displayed a good fungicidal activity against Physalospora piricola, which is equal to that of the positive control compound chlorothalonil.A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cyeloaddition between 4,6-dimethoxy-2-[（4-prop-2-ynyl）piperazin-l-yl]pyrimidine and each of different azides catalysed by in situ generated Cu（I）. The O-acyl protecting groups on glycosyl 1,2,3-triazoles were removed by triethylamine in wet methanol. Their chemical structures were established on the basis of corresponding tH NMR, 13C NMR, MS and elemental analysis. The fungicidal activities of target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Phytophthora capsici, Cercospora arachi- dicola and Gibberella zeae at 50 μg/mL. The bioassay results indicate that some of the compounds exhibited mode- rate but promising fungicidal activities. In particular, acetylated glucopyranosyl triazole displayed a good fungicidal activity against Physalospora piricola, which is equal to that of the positive control compound chlorothalonil.

关 键 词：1 H-1 2 3-Triazole Fungicidal activity Huisgen cycloaddition reaction Pyrimidinylpiperzine 

分 类 号：TQ613.4[化学工程—精细化工] S482.39[农业科学—农药学]