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化学学报
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化学学报 ›› 2010, Vol. 68 ›› Issue (16): 1577-1584. 上一篇    下一篇

研究论文

新型3,6-二取代-1,2,4-三唑[3,4-b]-1,3,4-噻二唑衍生物的合成、表征及生物活性

李英俊*,1，刘丽军1，靳焜2，孙淑琴1，许永廷3   

  1. (1辽宁师范大学化学化工学院 大连 116029)
    (2大连理工大学精细化工国家重点实验室 大连 116012)
    (3辽宁师范大学分析测试中心 大连 116029)
  • 投稿日期:2009-12-28 修回日期:2010-03-02 发布日期:2010-04-29
  • 通讯作者: 李英俊 E-mail:chemlab.lnnu@163.com
  • 基金资助:

    辽宁省教育厅高等学校科研基金资助项目

Synthesis and Biological Activities of Novel 3,6-Disubstituted 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazoles

Li Yingjun*,1 Liu Lijun1 Jin Kun2 Sun Shuqin1 Xu Yongting3   

  1. (1 College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029)
    (2 State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012)
    (3 Analysis and Inspection Center, Liaoning Normal University, Dalian 116029)
  • Received:2009-12-28 Revised:2010-03-02 Published:2010-04-29

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以4-氨基-5-[2-(4-氯苯氧甲基苯并咪唑)-1-亚甲基]-3-巯基-1,2,4-三唑(6)和不同的芳香酸为原料, 在三氯氧磷的作用下环化合成了17个新型3-[2-(4-氯苯氧甲基苯并咪唑)-1-亚甲基]-6-芳基-1,2,4-三唑[3,4-b]-1,3,4-噻二唑衍生物7. 利用IR, 1H NMR和元素分析对新化合物6和7的结构进行了表征. 初步的生物活性实验结果表明, 化合物7a和7b在20 μg/mL时对大肠杆菌甲硫氨酰氨肽酶(EcMetAP1)具有较高的抑制活性, 抑制率分别为87.26%和82.62%, 化合物7f, 7h和7l具有中等的抑制活性. 化合物7a～7q在20 μg/mL时对细胞分裂周期(cdc25B)磷酸酯酶均具有抑制活性, 其中化合物7b, 7g和7i在5 μg/mL时仍具有很高的抑制活性, 抑制率分别为98.76%, 83.87%和90.57%. 杀菌、杀虫、除草和植物生长调节活性筛选测定实验结果表明, 所测试的目标化合物7d～7e, 7h～7m和7o～7q均无活性.

关键词: 三唑并噻二唑, 合成, 表征, 生物活性

Seventeen novel 6-aryl-3-[2-(4-chlorophenoxymethylbenzimidazole)-1-methylene]-1,2,4-tria- zolo[3,4-b]-1,3,4-thiadiazoles 7 were synthesized by the condensation of 4-amino-5-[2-(4-chlorophenoxy- methylbenzimidazole)-1-methylene]-3-mercapto-1,2,4-triazole (6) with various aromatic acids in the prese- nce of phosphorous oxychloride. The structures of the intermediate 6 and the target compounds 7 were characterized by IR, 1H NMR techniques and elemental analysis. Preliminary bioassay indicated that the target compounds 7a and 7b exhibited higher inhibitory activity to EcMetAP1 with the inhibition of 87.26% and 82.62% respectively, compounds 7f, 7h and 7l showed moderate activity at the concentration of 20 μg/mL. The compounds 7a～7q had obvious inhibition to the cell devision cycle 25B phosphatase at 20 μg/mL and the compounds 7b, 7g and 7i still had higher inhibition even at 5 μg/mL with the inhibition of 98.76%, 83.87% and 90.57% respectively. The results of screening for fungicidal, insecticidal, herbicidal and plant growth regulating activities indicated that the tested target compounds 7d～7e, 7h～7m and 7o～7q all showed no activities.

Key words: triazolo-thiadiazoles, synthesis, characterization, bioactivities