Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 871-883.DOI: 10.6023/cjoc202108031 Previous Articles     Next Articles



王秀a, 段文贵a,*(), 林桂汕a,*(), 李宝谕a, 张文静a, 雷福厚b   

  1. a 广西大学化学化工学院 南宁 530004
    b 广西民族大学 广西林产化学与工程重点实验室 南宁 530008
  • 收稿日期:2021-08-18 修回日期:2021-10-07 发布日期:2021-11-03
  • 通讯作者: 段文贵, 林桂汕
  • 基金资助:
    国家自然科学基金(31870556); 广西林产化学与工程重点实验室开放基金(GXFG2010)

Synthesis, Antifungal Activity, Three-Dimensional Quantitative Structure-Activity Relationship and Molecular Docking Study of 4-Acyl-3-amino-1,2,4-triazole-thioether Derivatives Containing Natural Pinene Structure

Xiu Wanga, Wengui Duana(), Guishan Lina(), Baoyu Lia, Wenjing Zhanga, Fuhou Leib   

  1. a School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
    b Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi University for Nationalities, Nanning 530008
  • Received:2021-08-18 Revised:2021-10-07 Published:2021-11-03
  • Contact: Wengui Duan, Guishan Lin
  • Supported by:
    National Natural Science Foundation of China(31870556); Open Fund of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products(GXFG2010)

Twenty-four 4-acyl-3-amino-1,2,4-triazole-thioether derivatives containing natural pinene structure were designed and synthesized in search of novel natural product-based bioactive molecules. Their structures were characterized by IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The in vitro antifungal activity test of the target compounds showed that, at the concentration of 50 µg/mL, the target compounds displayed certain antifungal activity against the eight tested plant pathogens, in which 4 compounds exhibited good to excellent antifungal activity against Physalospora piricola, much better than that of the positive control chlorothalonil. Also, 2 compounds exhibited good inhibitory activity against Cercospora arachidicola, much better than that of the positive control chlorothalonil. The preliminary analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the molecular field analysis (CoMFA) method for the inhibitory activity of the target compounds against P. piricola, and a reasonable 3D-QSAR model (r2=0.961, q2=0.613) has been established. Furthermore, the molecular docking results showed that the binding mode of the target compound nopol-derived 4-(4'-fluorobenzoyl)-3-amino-1,2,4-triazole-thioether (5k) in the active cavity of succinate dehydrogenase (SDH) was similar to that of the commercial fungicide carboxin.

Key words: β-pinene, nopol, 1,2,4-triazole-thioether, 3D-QSAR, molecular docking, antifungal activity