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
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沈阳化工大学材料科学与工程学院沈阳 110142