Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 607-618.DOI: 10.6023/cjoc202108009 Previous Articles     Next Articles



王伟a, 武复冉a, 马一丹a, 徐丹b,c,*(), 徐功a,c,*()   

  1. a 西北农林科技大学植物保护学院 陕西杨凌 712100
    b 西北农林科技大学化学与药学院 陕西杨凌 712100
    c 西北农林科技大学旱区作物逆境生物学国家重点实验室 陕西杨凌 712100
  • 收稿日期:2021-08-07 修回日期:2021-09-18 发布日期:2022-02-24
  • 通讯作者: 徐丹, 徐功
  • 基金资助:
    陕西省自然科学基础研究计划(2021JQ-157); 陕西省重点研发计划(2021NY-140); 中央高校基本科研业务费专项资金(2452019189); 中央高校基本科研业务费专项资金(2452018318)

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

Wei Wanga, Furan Wua, Yidan Maa, Dan Xub,c(), Gong Xua,c()   

  1. 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
  • Received:2021-08-07 Revised:2021-09-18 Published:2022-02-24
  • Contact: Dan Xu, Gong Xu
  • 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)

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.

Key words: pyrazole, benzamide, antifungal activity, structure-activity relationships