ARTICLES

Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit

  • Wei Wang ,
  • Furan Wu ,
  • Yidan Ma ,
  • Dan Xu ,
  • Gong Xu
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  • a College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100
    b College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100
    c State Key Laboratory of Crop Stress Biology for Arid Areas, Northwest A&F University, Yangling, Shaanxi 712100
* Corresponding authors. E-mail: ;

Received date: 2021-08-07

  Revised date: 2021-09-18

  Online published: 2022-02-24

Supported by

Natural Science Basic Research Program of Shaanxi Province(2021JQ-157); Key Research and Development Program of Shaanxi Province(2021NY-140); Fundamental Research Funds for the Central Universities(2452019189); Fundamental Research Funds for the Central Universities(2452018318)

Abstract

To promote the discovery and development of new fungicides, a series of novel 1-methyl-pyrazol-5-yl-amino- phenyl-benzamide derivatives were designed and synthesized by active fragment splicing strategy, and the benzamide and pyrazole ring were connected together by imine bond. All of the target compounds were identified by NMR and high resolution mass spectrometry (HRMS), and evaluated for their antifungal activities. The bioassay data revealed that 4-chloro-N-(2-((1- methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)amino)phenyl)benzamide (14) exhibited an excellent in vitro activity against Sclerotinia sclerotiorum and Altenaria alternariae with EC50 value of 11.21 and 16.70 mg/L, respectively. For Valsa mali, compound 14 (EC50=11.67 mg/L) showed a significantly higher activity than the control of fluxapyroxad (EC50=16.49 mg/L). The molecular docking simulation revealed that compound 14 interacted with TYR 58 and ARG 43 of the succinate dehydrogenase (SDH) through hydrogen bond and p-π interaction, which could explain the probable mechanism of the action between compound 14 and target protein. These results indicate that compound 14 may be a potential SDH inhibitor and provide a valuable reference for further research.

Cite this article

Wei Wang , Furan Wu , Yidan Ma , Dan Xu , Gong Xu . Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit[J]. Chinese Journal of Organic Chemistry, 2022 , 42(2) : 607 -618 . DOI: 10.6023/cjoc202108009

References

[1]
Liu, Z.; Li, Q. X.; Song, B. J. Agric. Food Chem. 2020, 68, 11039.
[2]
Fisher, M. C.; Hawkins, N. J.; Sanglard, D.; Gurr, S. J. Science 2018, 360, 739.
[3]
Wang, W.; Zhang, S.; Wang, J. H.; Wu, F. R.; Wang, T.; Xu, G. J. Agric. Food Chem. 2021, 69, 491.
[4]
Patriarca, A. Curr. Opin. Food Sci. 2019, 29, 42.
[5]
Wang, W.; Cheng, X.; Cui, X.; Xia, D. G.; Wang, Z. Q.; Lü, X. H. Pest Manage. Sci. 2021, 77, 3529.
[6]
Ishii, H.; Zhen, F.; Hu, M. J.; Li, X. P.; Schnabel, G. Pest Manage. Sci. 2016, 72, 1844.
[7]
Li, H.; Gao, M. Q.; Chen, Y.; Wang, Y. X.; Yang, G. F. J. Agric. Food Chem. 2020, 68, 14001.
[8]
Wei, G.; Huang, M.-W.; Wang, W.-J.; Wu, Y.; Mei, S.-F.; Zhou, L.-M.; Mei, L.-C.; Zhu, X.-L.; Yang, G.-F. J. Agric. Food Chem. 2021, 69, 3965.
[9]
Xiong, L.; Li, H.; Jiang, L.-N.; Ge, J.-M.; Yang, W.-C.; Zhu, X. L.; Yang, G.-F. J. Agric. Food Chem. 2017, 65, 1021.
[10]
Xiong, L.; Zhu, X.-L.; Gao, H.-W.; Fu, Y.; Hu, S.-Q.; Jiang, L.-N.; Yang, W.-C.; Yang, G.-F. J. Agric. Food Chem. 2016, 64, 4830.
[11]
Xiong, L.; Shen, Y.-Q.; Jiang, L.-N.; Zhu, X.-L.; Yang, W.-C.; Huang, W.; Yang, G.-F. ACS Symp. Ser. 2015, 1204, 175.
[12]
Bardas, G. A.; Veloukas, T.; Koutita, O.; Karaoglanidis, G. S. Pest Manage. Sci. 2010, 66, 967.
[13]
Xiong, L.; Zhu, X.-L.; Shen, Y.-Q.; Wishwa, W. K. W. M.; Li, K.; Yang, G.-F. Eur. J. Med. Chem. 2015, 95, 424.
[14]
Guo, X. F.; Zhao, B.; Fan, Z. J.; Yan, D. Y.; Zhang, N. L.; Wu, Q. F.; Yu, B.; Zhou, S.; Kalinina, T. A.; Belskaya, N. P. J. Agric. Food Chem. 2019, 67, 1647.
[15]
Jones, D. Nat. Rev. Drug Discovery 2010, 9, 751.
[16]
Wang, W.; Wang, J. H.; Wu, F. R.; Zhou, H.; Xu, D.; Xu, G. J. Agric. Food Chem. 2021, 69, 5746.
[17]
Katte, T. A.; Reekie, T. A.; Jorgensen, W. T.; Kassiou, M. J. Org. Chem. 2016, 81, 4883.
[18]
Li, A.; Li, Z.; Zhao, Y.; Yao, T.; Zhao, J. Chin. J. Org. Chem. 2020, 40, 2836. (in Chinese)
[18]
( 李安邦, 李中珊, 赵洋, 姚停停, 程敬丽, 赵金浩, 有机化学, 2020, 40, 2836.)
[19]
Liu, H.; Xia, D. G.; Hu, R.; Wang, W.; Cheng, X.; Wang, A. L.; Zhang, Q.; Lü, X. H. Pestic. Biochem. Physiol. 2020, 163, 271.
[20]
Lü, X. H.; Ren, Z. L.; Liu, P.; Li, B. X.; Li, Q. S.; Chu, M. J.; Cao, H. Q. Pest Manage. Sci. 2017, 73, 1585.
[21]
Zhu, X. L.; Xiong, L.; Li, H.; Song, X. Y.; Liu, J. J.; Yang, G. F. ChemMedChem 2014, 9, 1512.
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