Citation: Wu Shaojie, Lu Yiming, Lei Zhuonan, Jiang Yan, Zhang Wenhui, Qi Le, Ma Haixia, Ren Yinghui. Synthesis, Biological Activity and Molecular Docking of 4-Amino-5-substituted-1, 2, 4-triazole-3-thione Schiff Base[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1939-1944. doi: 10.6023/cjoc201811016 shu

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

Department of Chemical Engineering, Northwest University, Xi'an 710069

Corresponding author: Ren Yinghui, nwuryh@163.com
Received Date: 11 November 2018
Revised Date: 21 January 2019
Available Online: 2 July 2019
Fund Project: the Innovation and Entrepreneurship Training Program for Undergraduates in Northwest University 2018377the Provincial Key-point Natural Science Foundation of Shaanxi Province 2016JZ003Project 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)the Innovation and Creativity Funds for Graduates in Northwest University YZZ17137

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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.
- pyrimidine,
- 1, 2, 4-triazole,
- Schiff base compounds,
- biological activity,
- molecular docking
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