有机化学 ›› 2017, Vol. 37 ›› Issue (10): 2705-2710.DOI: 10.6023/cjoc201704032 上一篇    下一篇

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研究论文

新型吡唑酰基硫脲类化合物的设计合成、杀菌活性与分子对接研究

孙娜波a, 沈钟华b, 翟志文b, 韩亮b, 翁建全b, 谭成侠b, 刘幸海b   

  1. a 浙江树人大学生物与环境工程学院 杭州 310015;
    b 浙江工业大学化学工程学院 杭州 310014
  • 收稿日期:2017-04-18 修回日期:2017-06-02 发布日期:2017-06-16
  • 通讯作者: 刘幸海 E-mail:xhliu@zjut.edu.cn
  • 基金资助:

    浙江省自然科学基金(No.LY16C14007)和国家自然科学基金(No.31401691)资助项目.

Design,Synthesis,Fungicidal Activity and Docking Study of Acyl Thiourea Derivatives Containing Pyrazole Moiety

Sun Naboa, Shen Zhonghuab, Zhai Zhiwenb, Han Liangb, Weng Jianquanb, Tan Chengxiab, Liu Xinghaib   

  1. a College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015;
    b College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
  • Received:2017-04-18 Revised:2017-06-02 Published:2017-06-16
  • Contact: 10.6023/cjoc201704032 E-mail:xhliu@zjut.edu.cn
  • Supported by:

    Project supported by the Natural Science Foundation of Zhejiang Province (No.LY16C14007) and the National Natural Science Foundation of China (No.31401691).

以乙酰乙酸乙酯、原甲酸三乙酯、甲基肼等为原料,通过多步反应制备了一系列吡唑酰基硫脲类化合物,产物结构均经过1H NMR,13C NMR和HRMS确证.对所有化合物进行了杀菌活性测试,结果表明部分化合物对苹果轮纹病具有较好的抑制效果,同时将高活性化合物N-(2,6-二乙基苯基)-1,3-二甲基-1H-吡唑-4-酰基硫脲(6k)与琥珀酸脱氢酶进行了对接.对接结果表明,化合物6k能与琥珀酸脱氢酶形成稳定的复合物,形成氢键和π(σ)-π相互作用.

关键词: 吡唑, 酰基硫脲, 合成, 杀菌活性, 分子对接

A series of novel acyl thiourea derivatives containing pyrazole moiety were designed and synthesized from ethyl acetoacetate, triethyl orthoformate, methylhydrazine by multi-step reactions. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The target compounds were evaluated for their fungicidal activity. The results indicated that some of the title compounds displayed certain fungicidal activities against Botryospuaeria berengeriana. The docking results indicated that the hydrogen bond and π(σ)-π interaction formed between N-((2,6-diethylphenyl)carbamothioyl)-1,3-dimethyl-1H-pyrazole-4-carboxamide (6k) and succinodehydrogenase.

Key words: pyrazole, acyl thiourea, synthesis, fungicidal activity, docking