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

doi:10.6023/cjoc201811016

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

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 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

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

Received:2018-11-11 Revised:2019-01-21 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).

1. Synthesis, Biological Activity and Molecular Docking of 4-Amino-5-substituted-1,2,4-triazole-3-thione Schiff Base.PDF(417KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(7): 1939-1944.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Jin, R. Y. Ph. D. Dissertation, Northwest University, Xi'an, 2015 (in Chinese). (靳如意, 博士论文, 西北大学, 西安, 2015).
[2] Abele, E.; Abele, R.; Lukevics, E. Chem. Heterocycl. Compd. 2008, 44, 769.
[3] Kauthale, S.; Tekale, S.; Damale, M.; Sangshetti, J.; Pawar, R. Bioorg. Med. Chem. Lett. 2017, 27, 3891.
[4] Jiang, S. L.; Han, L. Chin. J. Org. Chem. 2012, 32, 930(in Chinese). (蒋绍亮, 韩亮, 有机化学, 2012, 32, 930.)
[5] Ren, G, Y. Ph. D. Dissertation, Northwest University, Xi'an, 2018 (in Chinese). (任国瑜, 博士论文, 西北大学, 西安, 2018.)
[6] Jin, R. Y.; Zeng, C. Y.; Liang, X. H.; Sun, X. H.; Liu, Y. F.; Wang, Y. Y.; Zhou, S. Bioorg. Chem. 2018, 80, 252.
[7] Sun, X. H.; Tao, Y.; Liu, Y. F.; Jia, Y.Q.; Chen, B. Acta Chim. Sinica 2008, 33, 234(in Chinese). (孙晓红, 陶燕, 刘源发, 贾婴琦, 陈邦, 化学学报, 2008, 33, 234.)
[8] Roman, G. Eur. J. Med. Chem. 2015, 89, 744.
[9] Ünver, Y.; Dügdü, E.; Sancak, K.; Mustafa, E. R.; Karaoglu, S. A. Turk. J. Chem. 2009, 33, 135.
[10] Tehrani, K., Mashayekhi, V.; Azerang, P.; Minaei, S.; Sardari, S.; Kobarfard, F. Ir. J. Pharm. Res. 2015, 14, 63.
[11] Tao, Y.; Sun, X. H.; Liu, Y. F.; Chen, B. Chem. Bioeng. 2016, 33, 50(in Chinese). (陶燕, 孙晓红, 刘源发, 陈邦, 化学与生物工程, 2016, 33, 50.)
[12] Jin, R. Y.; Sun, X. H.; Liu, Y. F.; Ma, H. X. Chemistry 2013, 76, 850(in Chinese). (靳如意, 孙晓红, 刘源发, 马海霞, 化学通报, 2013, 76, 850.)
[13] Zhao, P. L.; Chen, P.; Li, Q.; Hu, M. J.; Diao, P. C.; Pan, E. S.; You, W. W. Bioorg. Med. Chem. Lett. 2016, 26, 3680.
[14] Du, H. T.; Du, H. J. Chin. J. Org. Chem. 2010, 30, 138(in Chinese). (杜海堂, 杜海军, 有机化学, 2010, 30, 138.)
[15] Sahoo, K. P.; Sharma, R.; Pattanayak, P. Med. Chem. Res. 2010, 19, 129.
[16] Bhasin, G.; Srivastava, R.; Singh, R. Org. Prep. Proced. Int. 2017, 49, 371.
[17] Xie, W. L.; Zhang, J. G.; Ma, X. J.; Yang, W. Q.; Zhou, Y.; Tang, X. F.; Zou, Y.; Li, H.; He, J. J.; Xie, S. M.; Zhao, Y. H.; Liu, F. P. Chem. Biol. Drug. Des. 2015; 86, 1088.
[18] Magdy, S.; Omima, M. I. A.; Abdelrhman, E. M.; EI-Shetary, B. A. J. Mol. Struct. 2017, 1145, 330.
[19] Lu, W. T.; Sun, X. H.; Liu, Y. F.; Jin, R. Y. Chemistry 2012, 75, 362(in Chinese). (陆文婷, 孙晓红, 刘源发, 靳如意, 化学通报, 2012, 75, 362)
[20] Tang, G. H.; Zhang, Y.; Zhang Y. P.; Zhou, P. P.; Lin, Z. H.; Wang, Y. Q. Chem. J. Chin. Univ. 2017, 38, 2062(in Chinese). (唐光辉, 张娅, 张玉萍, 周朋朋, 林治华, 王远强, 高等化学学报, 2017, 38, 2062.)
[21] Beteringhe, A.; Racuciu, C.; Balan, C.; Stoican, E.; Patron, L. Adv. Mater. Res. 2013, 787, 236.
[22] El Bindary, A. A.; Shoair, A. F.; El-Sonbati, A. Z.; Diab, M. A.; Abdo, E. E. J. Mol. Liq. 2015, 212, 579.
[23] Wu, A. B. Ph.D. Dissertation, Huazhong Agricultural University, Wuhan, 2005 (in Chinese). (武爱波, 博士论文, 华中农业大学, 武汉, 2005.)
[24] Park, Y.; Cho, Y.; Lee, Y. H.; Lee, Y. W.; Rhee, S. J. Struct. Biol. 2016, 194, 395.
[25] Abd-Rabou, A. A.; Abdel-Wahab, B. F.; Bekheit, M. S. Chem. Pap. 2018, 72, 2231.
[26] El Ashry El Sayed H. El Ashry.; El Sayed H. El Tamany.; Mohy El Din Abd El Fattah.; Ahmed T. A. Boraei.; Heba M. Abd El-Nabi. Eu. J. Med. Chem. 2013, 66, 112.
[27] Zhou, J. H.; Li, J. J.; Li, J.; Ren, G. Y.; Ren, R. Y.; Ma, H. X. Chem. Res. Chin. Univ. 2017, 33, 866.

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

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[2]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[3]	Chuantao Zhu, Song Wang, Yifan Zhao, Piet Herdewijn, Fengwu Liu. Synthesis of Novel 2,2'-Anhydro-L-threosylpyrimidine Phosphonates [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3167-3173.
[4]	Mingjia Guang, Shuo Jiang, Baoyu Zhu, Rusong Zhang, Kunpeng Wang, Minghui Wang, Liangzhong Xu. Design, Synthesis and Insecticidal, Acaricidal Activities of Novel Pyrrole-2-carboxylic Acid and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2895-2904.
[5]	Feng Wang, Yu Chen, Hongyan Pei, Jing Zhang, Lixin Zhang. Design, Synthesis and Antifungal Activities of Novel 1,2,4-Oxadiazole Derivatives Containing Piperidine [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2826-2836.
[6]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[7]	Hai Lin, Huixiang Nie, Anlin Zhao, Tao Wang, Jin Luo. Synthesis and Herbicidal Activity of Novel Pyrimido[5,4-e]-[1,2,4]triazolo[1,5-c]pyrimidine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2462-2475.
[8]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[9]	Huan Xu, Hongfei Wu, Xiaoming Zhang, Xingxing Lu, Tengda Sun, Yue Qi, Yufan Lin, Xinling Yang, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 725-733.
[10]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[11]	Tian Sang, Fan Jia, Jing He, Chuntian Li, Yan Liu, Ping Liu. I₂-Catalyzed Cyclization of β-Ketonitrile with 1H-Pyrazol-5-amine [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 195-201.
[12]	Changxing Sun, Fuhao Zhang, Huan Zhang, Penghui Li, Lin Jiang. Design, Synthesis, Fungicidal Activity and Molecular Docking Study of Novel 2-(1-Methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 229-235.
[13]	Chao Gao, Xiaojie Si, Lingling Chi, Hao Wang, Honglin Dai, Limin Liu, Zhengjie Wang, Yang Zhang, Tao Wang, Yaochuan Zhou, Jiaxin Zheng, Yu Ke, Hongmin Liu, Qiurong Zhang. Synthesis and Antiproliferative Activity of 2,4,5,6-Tetrasubstituted Pyrimidine Derivatives Containing Anisole [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1677-1686.
[14]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[15]	Can Yong, Yun Li, Tao Bi, Guofeng Chen, Dongxia Zheng, Zhouyu Wang, Yuanyuan Zhang. Research Progress on the Synthesis and Activity of D-Galactose Derived Small Galectin Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1307-1325.