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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (05): 758-763. 上一篇    下一篇

研究论文

5-(2-芳氧甲基苯并咪唑-1-亚甲基)-1,3,4-噁二唑-2-硫酮的合成、 晶体结构及生物活性研究

魏太保 ; 陈 靖 ; 徐 蓉; 张有明*   

  1. (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)
  • 收稿日期:2008-09-09 修回日期:2008-12-02 发布日期:2009-05-20
  • 通讯作者: 张有明

Synthesis, Crystal Structure and Biological Activities of 5-(2-Aryloxy- methylbenzimidazole-1-carbadehyde)-1,3,4-oxadiazole-2-thione

Wei, Taibao ; Chen, Jing ; Xu, Rong ; Zhang, Youming*   

  1. (Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal
    University, Lanzhou 730070)
  • Received:2008-09-09 Revised:2008-12-02 Published:2009-05-20
  • Contact: Zhang, Youming

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1260

被引次数

27

以2-芳氧甲基苯并咪唑-1-乙酰肼类化合物为原料在微波辐射条件下合成了10种尚未见文献报道的5-(2-芳氧甲基苯并咪唑-1-亚甲基)-1,3,4-噁二唑-2-硫酮衍生物, 化合物结构经 IR, 1H NMR, 13C NMR 和元素分析进行了表征. 6a 晶体结构表明, 该化合物通过分子间氢键自组装成了沿b轴无限延伸的一维链状超分子结构, 属于单斜晶系, P21/c空间群, a＝11.5484(13) Å, b＝16.5319(19) Å, c＝11.3595(14) Å, β＝108.755(2)°, Z＝2, V＝2053.6(4) Å3, Dx＝1.328 g/cm3, F(000)＝860, µ＝0.19 mm－1, R＝0.060, wR＝0.196. 初步生物活性试验结果表明该系列部分化合物对油菜幼苗的生长具有明显的生长调节作用, 并对枯草杆菌具有一定的抑制作用.

关键词: 合成, 晶体结构, 生物活性, 5-(2-芳氧甲基苯并咪唑-1-亚甲基)-1,3,4-噁二唑-2-硫酮

A series of new 5-(2-aryloxymethylbenzimidazole-1-carbadehyde)-1,3,4-oxadiazole-2-thione were synthesized by 2-[(un)substituted phenoxymethyl]benzimidazole-1-acetohydrazides under microwave irradiation conditions. The structures of all synthesized compounds were confirmed by IR, 1H NMR, 13C NMR spectra and elemental analysis. In the crystal of 6a , the compound was assembled to a linear su-pramolecular structure along axis b by the intermolecular hydrogen bonds. Crystal data: monoclinic, space group P21/c, a＝11.5484(13) Å, b＝16.5319(19) Å, c＝11.3595(14) Å, β＝108.755(2)°, Z＝2; V＝2053.6(4) Å3, Dx＝1.094 g/cm3, F(000)＝860, µ＝0.19 mm－1, R＝0.060, and wR＝0.196. The preliminary biological activity tests show that some of the title compounds have obvious regulating activities for the growth of the rape, and some compounds such as 6a and 6h possess satisfactory activity of growth inhibition against B. subtilis at a test concentration.

Key words: synthesis, crystal structure, bioactivity
, 5-(2-aryloxymethylbenzimidazole-1-carbadehyde)-1,3,4-oxadiazole-2-thione