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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (04): 569-575. 上一篇    下一篇

研究论文

N-(1,2,4-三唑)含氟肉桂醛亚胺的合成及生物活性

李黔柱a,b 宋宝安*,a 蔡学建a 郑玉国a 郭晴晴a   

  1. (a贵州大学精细化工研究开发中心 教育部绿色农药和农业生物工程重点实验室 贵阳 550025) 
    (b毕节学院化学系 毕节 551700)
  • 收稿日期:2009-02-25 修回日期:2009-10-20 发布日期:2009-12-02

Synthesis and Bioactivities of Novel N-1,2,4-Triazole Moieties Imines Containing Fluorocinnamylidene

Li, Qianzhu a,b Song, Baoan *,a Cai, Xuejiana Zheng, Yuguoa Guo, Qingqinga   

  1. (a Key Laboratory of Green Pesticide and Bioengineering, Ministry of Educational, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025) 
    (b Department of Chemistry, Bijie University, Bijie 551700)
  • Received:2009-02-25 Revised:2009-10-20 Published:2009-12-02

PDF

558

被引次数

36

含氟肉桂醛与4-氨基-5-(3,4,5-三甲氧基苯基)-1,2,4-三唑-3-硫酮(2)缩合生成5-(3,4,5-三甲氧基苯基)-4-取代苯基烯丙亚胺基-1,2,4-三唑-3-硫酮(3), 再烷基化为新型含氟肉桂醛1,2,4-三唑亚胺(4). 化合物结构经1H NMR, 13C NMR, IR以及元素分析确认, 并用X-ray单晶衍射测定了化合物4g的晶体结构, 证实了分子中两个环外双键N＝C和C＝C均为E-式构型. 初步生物活性测试结果表明, 部分化合物具有抗植物病毒活性.

关键词: 含氟肉桂醛, 1,2,4-三唑, 亚胺, 晶体结构, 生物活性

A series of 4-(substituted-3-phenylallylideneamino)-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-tria- zole-5(4H)-thione (3) were synthesized by condensation reaction of 4-amino-3-(3,4,5-trimethoxyphenyl)- 1H-1,2,4-triazole-5(4H)-thione (2) with various fluorocinnamaldehydes. Alkylation of 3 with alkyl halides affordedN-1,2,4-triazole moieties imines containing fluorocinnamylidene 4. Their structures were confirmed by 1H NMR, 13C NMR, IR and elemental analyses. The single crystal structure of compound 4g was determined by X-ray diffraction analysis, which revealed that the two double bonds N＝C and C＝Coutside the rings were of E,E-configurations. The preliminary bioassay showed that some of them exhibited moderate antiviral activity.

Key words: fluorocinnamaldehyde, 1,2,4-triazole, imines, crystal structure, bioactivity