Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 1939-1944.DOI: 10.6023/cjoc201811016 Previous Articles     Next Articles

Articles

4-氨基-5-取代-1,2,4-三唑-3-硫酮席夫碱的合成、生物活性及分子对接

武少婕, 卢一鸣, 雷卓楠, 蒋演, 张文慧, 齐乐, 马海霞, 任莹辉   

  1. 西北大学化工学院 西安 710069
  • 收稿日期:2018-11-11 修回日期:2019-01-21 出版日期:2019-07-25 发布日期:2019-04-08
  • 通讯作者: 任莹辉 E-mail:nwuryh@163.com
  • 基金资助:

    陕西省重点自然科学基金(No.2016JZ003)、西北大学研究生自主创新项目(No.YZZ17137)、西北大学大学生创新创业训练计划(No.2018377)资助项目.

Synthesis, Biological Activity and Molecular Docking of 4-Amino-5-substituted-1,2,4-triazole-3-thione Schiff Base

Wu Shaojie, Lu Yiming, Lei Zhuonan, Jiang Yan, Zhang Wenhui, Qi Le, Ma Haixia, Ren Yinghui   

  1. Department of Chemical Engineering, Northwest University, Xi'an 710069
  • Received:2018-11-11 Revised:2019-01-21 Online:2019-07-25 Published:2019-04-08
  • Contact: 10.6023/cjoc201811016 E-mail:nwuryh@163.com
  • Supported by:

    Project supported by the Provincial Key-point Natural Science Foundation of Shaanxi Province (No. 2016JZ003), the Innovation and Creativity Funds for Graduates in Northwest University (No. YZZ17137), the Innovation and Entrepreneurship Training Program for Undergraduates in Northwest University (No. 2018377).

In this paper, the intermediate of 4-amino-5-methyl-1,2,4-triazole-3-thione (M1) was synthesized with thioformyl hydrazide and acetic acid, and 4-amino-5-aryl-1,2,4-triazole-3-thione (M2) was got by esterification, hydrazide, salt formation and cyclization with substituted benzoic acid. Four compounds of 1,2,4-triazole Schiff bases containing the pyrimidine ring M1-1, M2-1, M2-2 and M2-3 were obtained with 4,6-dichloro-5-pyrimidinecarboxaldehyde and M1/M2 according to the addition-elimination reaction. The structures of the compounds were characterized by elemental analysis, IR and 1H NMR spectra. The bioactivities and antibacterial mechanism of the title compounds were also studied by mycelial growth rate method and molecular docking. The results showed that the compounds had certain inhibitory effects on different fungi. Based on the values of EC50, compounds M1-1, M2-2 and M2-3 have better antifungal effects against the wheat gibberella than that of the standard drug (fluconazole), which is corresponding to the result of molecular docking.

Key words: pyrimidine, 1,2,4-triazole, Schiff base compounds, biological activity, molecular docking