有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1820-1825. 上一篇    下一篇

研究简报

[5-(芳亚甲基氨基)-1,3,4-噻二唑-2-基]硫乙酰芳胺的合成及 生物活性研究

魏太保a ; 王文利a ; 郭潇迪a ; 徐 蓉a; 张有明*,a ; 达文燕b   

  1. (a西北师范大学化学化工学院 甘肃省高分子材料重点实验室 兰州 730070)
    (b西北师范大学生命科学学院 兰州 730070)
  • 收稿日期:2008-03-07 修回日期:2008-04-04 发布日期:2008-10-20
  • 通讯作者: 张有明

Synthesis and Biological Activity of [5-(Arylmethylideneamino)- 1,3,4-thiadiazol-2-yl]thioacetanilides

WEI, Tai-Baoa ; WANG, Wen-Lia ; GUO, Xiao-Dia ; XU, Ronga;
ZHANG, You-Ming*,a; DA, Wen-Yanb
  

  1. (a Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering,
    Northwest Normal University, Lanzhou 730070)
    (b College of Life Science, Northwest Normal University, Lanzhou 730070)
  • Received:2008-03-07 Revised:2008-04-04 Published:2008-10-20
  • Contact: ZHANG, You-Ming

在K2CO3存在下利用聚乙二醇-400 (PEG-400)作相转移催化剂, 于固-液相转移催化条件下, 通过5-芳亚甲基氨 基-2-巯基-1,3,4-噻二唑与氯乙酰芳胺的硫烷基化反应, 合成了16个未见文献报道的[5-(芳亚甲基氨基)-1,3,4-噻二唑-2-基]硫乙酰芳胺衍生物. 经元素分析, FT-IR,1H NMR和13C NMR确证了其结构. 生物活性实验结果表明, 部分化合物对小麦幼苗的生长具有明显的植物生长调节活性, 并对枯草杆菌具有一定的抑制活性.

关键词: [5-(芳亚甲基氨基)-1,3,4-噻二唑-2-基]硫乙酰芳胺, 合成, 相转移催化, 生物活性

Sixteen novel derivatives of [5-(arylmethylideneamino)-1,3,4-thiadiazol-2-yl]thioacetanilide were synthesized by the reaction of S-alkylation of 5-arylmethylideneamino-2-mercapto-1,3,4-thiadiazole with chloroacetanilides under the conditions of solid-liquid phase transfer catalysis using PEG-400 as a phase transfer catalyst in the presence of potassium carbonate. All the products were characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR spectra. The preliminary biological activity tests showed that some of the title compounds had obvious regulating activities for the growth of wheat, and some compounds such as 4a and 4e possessed satisfactory activity of growth inhibition against B. subtilis at a test concentration (20 mg/mL).

Key words: synthesis, [5-(arylmethylideneamino)-1,3,4-thiadiazol-2-yl]thioacetanilide, bioactivity, phase transfer catalysis