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

doi:10.1007/s40242-013-2338-x

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (5): 900-905.doi: 10.1007/s40242-013-2338-x

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

MAO Ming-zhen¹, LI Yu-xin¹, ZHOU Yun-yun¹, YANG Xiao-ping², ZHANG Xiu-lan¹, ZHANG Xiao¹, LI Zheng-ming¹

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

Received:2012-09-05 Revised:2012-09-26 Online:2013-10-01 Published:2013-09-17
Contact: LI Yu-xin, LI Zheng-ming E-mail:liyx128@nankai.edu.cn;nkzml@vip.163.com
Supported by:
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).

Abstract

Abstract:

A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cycloaddition between 4,6-dimethoxy-2-[(4-prop-2-ynyl)piperazin-1-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 corresponding¹H 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 arachidicola 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.

Key words: 1H-1,2,3-Triazole, Fungicidal activity, Huisgen cycloaddition reaction, Pyrimidinylpiperzine

MAO Ming-zhen, LI Yu-xin, ZHOU Yun-yun, YANG Xiao-ping, ZHANG Xiu-lan, ZHANG Xiao, LI Zheng-ming. Synthesis and Biological Activity of Novel 1-Substituted Phenyl(glycosyl)-4-{4-[(4,6-dimethoxy)pyrimidin-2-yl] Piperazin-1-yl}methyl-1H-1,2,3-triazoles[J]. Chemical Research in Chinese Universities, 2013, 29(5): 900-905.

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

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