Acta Chimica Sinica ›› 2010, Vol. 68 ›› Issue (16): 1577-1584. Previous Articles     Next Articles

Full Papers

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

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 7a7q 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 7d7e, 7h7m and 7o7q all showed no activities.

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