Citation: Zhang Jing-Peng, Li Xiang-Yang, Dong Ya-Wen, Qin Yao-Guo, Li Xin-Lu, Song Bao-An, Yang Xin-Ling. Synthesis and biological evaluation of 4-methyl-1, 2, 3-thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives[J]. Chinese Chemical Letters, ;2017, 28(6): 1238-1242. doi: 10.1016/j.cclet.2017.02.002 shu

Synthesis and biological evaluation of 4-methyl-1, 2, 3-thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives

a.
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
b.
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China

Corresponding author: Yang Xin-Ling, yangxl@cau.edu.cn
Received Date: 28 October 2016
Revised Date: 27 November 2016
Accepted Date: 27 December 2016
Available Online: 4 June 2017

Figures(5)

To find new lead compounds with high biological activity, a series of novel 4-methyl-1, 2, 3-thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives were designed and synthesized. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR spectrum and elemental analysis. Preliminary bioassay indicated that the title compounds exhibited moderate to strong fungicidal activity against six fungi in vitro at 50 μg/mL. Moreover, some of the title compounds exhibited good curative activity against TMV in vivo at 500 μg/mL. The structure-activity relationship analysis of compounds against Valsa mali showed that compounds containing halogen at the para position on phenyl exhibited the best activity. Especially compound 8k showed broad spectrum fungicidal activities against Valsa mali, Botrytis cinerea, Pythium aphanidermatum, Rhizoctonia solani, Fusarium moniliforme and Alternaria solani with the EC₅₀ values of 8.20, 24.42, 15.80, 40.53, 41.48, and 34.16 μg/mL, respectively.
- 1, 2, 3-Thiadiazole,
- Benzoyl hydrazone,
- Synthesis,
- Fungicidal activity,
- Curative activity against TMV,
- Structure-activity relationship
1. [1]
  Li F.Y., Guo X.F., Fan Z.J.. Synthesis and biological activities of novel 2-amino-1, 3-thiazole-4-carboxylic acid derivatives[J]. Chin. Chem. Lett., 2015,26:1315-1318. doi: 10.1016/j.cclet.2015.05.040
2. [2]
  Zhan P., Liu X.Y., Li Z.Y.. Novel 1, 2, 3-thiadiazole derivatives as HIV-1 NNRTIs with improved potency:synthesis and preliminary SAR studies[J]. Bioorg. Med. Chem., 2009,17:5920-5927. doi: 10.1016/j.bmc.2009.07.004
3. [3]
  Tripathy R., Ghose A., Singh J.. 12, 3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors[J]. Bioorg. Med. Chem. Lett., 2007,17:1793-1798. doi: 10.1016/j.bmcl.2006.12.054
4. [4]
  Zuo X., Mi N., Fan Z.J.. Synthesis of 4-methyl-12, 3-thiadiazole derivatives via Ugi reaction and their biological activities[J]. J. Agric. Food Chem., 2010,58:2755-2762. doi: 10.1021/jf902863z
5. [5]
  Wang S.X., Fang Z., Fan Z.J.. Synthesis of tetrazole containing 12, 3-thiadiazole derivatives via U-4CR and their anti-TMV activity[J]. Chin. Chem. Lett., 2013,24:889-892. doi: 10.1016/j.cclet.2013.05.026
6. [6]
  Dong W.L., Liu Z.X., Liu X.H., Li Z.M., Zhao W.G.. Synthesis and antiviral activity of new acrylamide derivatives containing 12, 3-thiadiazole as inhibitors of hepatitis B virus replication[J]. Eur. J. Med. Chem., 2010,45:1919-1926. doi: 10.1016/j.ejmech.2010.01.032
7. [7]
  Zhang J.P., Qin Y.G., Dong Y.W.. Synthesis and biological activities of (E)-β-farnesene analogues containing 1, 2, 3-thiadiazole[J]. Chin. Chem. Lett., 2017,28:372-376. doi: 10.1016/j.cclet.2016.10.030
8. [8]
  Fan Z.J., Shi Z.G., Zhang H.K.. Synthesis and biological activity evaluation of 12, 3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance[J]. J. Agric. Food Chem., 2009,57:4279-4286. doi: 10.1021/jf8031364
9. [9]
  Li Y.D., Mao W.T., Fan Z.J.. Synthesis and biological evaluation of novel 12, 4-triazole containing 1, 2, 3-thiadiazole derivatives[J]. Chin. Chem. Lett., 2013,24:1134-1136. doi: 10.1016/j.cclet.2013.06.024
10. [10]
  Du Q.S., Shi Y.X., Li P.F.. Novel plant activators with thieno[2, 3-d]-1, 2, 3-thiadiazole-6-carboxylate scaffold:synthesis and bioactivity[J]. Chin. Chem. Lett., 2013,24:967-969. doi: 10.1016/j.cclet.2013.07.003
11. [11]
  Xu W.M., Li S.Z., He M.. Synthesis and bioactivities of novel thioether/sulfone derivatives containing 12, 3-thiadiazole and 1, 3, 4-oxadiazole/thiadiazole moiety[J]. Bioorg. Med. Chem. Lett., 2013,23:5821-5824. doi: 10.1016/j.bmcl.2013.08.107
12. [12]
  Zhang P.Z., Zhou S.F., Li T.R., Jiang L.. Efficient synthesis and in vitro antifungal activity of 1H-benzimidazol-1-yl acetates/propionates containing 1H-12, 4-triazole moiety[J]. Chin. Chem. Lett., 2012,23:1381-1384. doi: 10.1016/j.cclet.2012.10.024
13. [13]
  Luo Y.P., Gong Q., Chen Q., Yang G.F.. Synthesis and herbicidal activities of tetrazolinone derivatives containing oxime ether[J]. Chin. J. Org. Chem., 2008,28:1561-1565.
14. [14]
  Teng X., Keys H., Jeevanandam A.. Structure-activity relationship study off[1, 2, 3] thiadiazole necroptosis inhibitors[J]. Bioorg. Med. Chem. Lett., 2007,17:6836-6840. doi: 10.1016/j.bmcl.2007.10.024
15. [15]
  Fan Z.J., Yang Z.K., Zhang H.K.. Synthesis crystal structure, and biological activity of 4-methyl-1, 2, 3-thiadiazole-containing 1, 2, 4-triazolo[3, 4-b] [1, 3, 4] thiadiazoles[J]. J. Agric. Food Chem., 2010,58:2630-2636. doi: 10.1021/jf9029628
16. [16]
  Zhang Z., Li Y.C., Fan W.X., Wan J.J.. Research progress of acylhydrazone compounds[J]. J. Anhui Agric. Sci., 2010,38:6644-6645.
17. [17]
  Han J., Zhou X.X., Chen S.B., An Y.. Synthesis and biological activities of novel acylhydrazonecontaining 12, 4-triazole structure[J]. Chin. J. Org. Chem., 2014,37:741-748.
18. [18]
  Xia Y., Fan C.D., Zhao B.X.. Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells[J]. Eur. J. Med. Chem., 2008,43:2347-2353. doi: 10.1016/j.ejmech.2008.01.021
19. [19]
  Loncle C., Brunel J.M., Vidal N., Dherbomez M., Letourneux Y.. Synthesis and antifungal activity of cholesterol-hydrazone derivatives[J]. Eur. J. Med. Chem., 2004,39:1067-1071. doi: 10.1016/j.ejmech.2004.07.005
20. [20]
  Hanna M.M.. New pyrimido[5, 4-e]pyrrolo[1, 2-c]pyrimidines:synthesis, 2DQSAR, anti-inflammatory, analgesic and ulcerogenicity studies[J]. Eur. J. Med. Chem., 2012,55:12-22. doi: 10.1016/j.ejmech.2012.06.048
21. [21]
  Cunha A.C., Figueiredo J.M., Tributino J.L.M.. Antiplatelet properties of novel N-substituted-phenyl-12, 3-triazole-4-acylhydrazone derivatives[J]. Bioorg. Med. Chem., 2003,11:2051-2059. doi: 10.1016/S0968-0896(03)00055-5
22. [22]
  Melnyk P., Leroux V., Sergheraert C., Grellier P.. Design, synthesis and in vitro antimalarial activity of an acylhydrazone library[J]. Bioorg. Med. Chem. Lett., 2006,16:31-35. doi: 10.1016/j.bmcl.2005.09.058
23. [23]
  Huang W., Yang G.F.. Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles[J]. Bioorg. Med. Chem., 2006,14:8280-8285. doi: 10.1016/j.bmc.2006.09.016
24. [24]
  N.C. Chen, Technology of Pesticide Bioassay, Beijing Agricultural University Press, Beijing, 1991, pp. 161-162.
25. [25]
  Song B.A., Zhang H.P., Wang H.. Synthesis and antiviral activity of novel chiral cyanoacrylate derivatives[J]. J. Agric. Food Chem., 2005,53:7886-7891. doi: 10.1021/jf051050w
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
4. [4]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
5. [5]
  Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
6. [6]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
7. [7]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
8. [8]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
9. [9]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
10. [10]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
11. [11]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466
12. [12]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
13. [13]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
14. [14]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
15. [15]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
16. [16]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
17. [17]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
18. [18]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
19. [19]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
20. [20]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1287)
HTML views(48)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142