Design, Synthesis, and Antiviral Activities of Coumarin Derivatives Containing Dithioacetal Structures

被引:50
|
作者
Zhao, Lei [1 ]
Zhang, Jian [1 ]
Liu, Ting [1 ]
Mou, Honglan [1 ]
Wei, Chunle [1 ]
Hu, Deyu [1 ]
Song, Baoan [1 ]
机构
[1] Guizhou Univ, Guiyang, Peoples R China
基金
中国国家自然科学基金;
关键词
coumarin; dithioacetal; tobacco mosaic virus; transmission electron microscopy; molecular docking; TOBACCO-MOSAIC-VIRUS; INHIBITORS; DISCOVERY; MOIETY;
D O I
10.1021/acs.jafc.9b06861
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
In this study, a series of coumarin derivatives containing dithioacetals were synthesized, characterized, and assessed for their anti-tobacco mosaic virus (TMV) activities. Biological tests showed that most of the title compounds exhibited significant anti-TMV biological activities; in particular, compound b21 showed good inactivating activity anti-TMV, with an EC50 of 54.2 mg/L, superior to that of ribavirin (134.2 mg/L). Transmission electron microscopy analyses showed that compound 21 severely ruptured TMV particles. The interaction of compound b21 with TMV coat protein (TMV CP) was investigated using microscale thermophoresis and molecular docking. Compound b21 exhibited a strong binding ability to TMV CP, with a value of 2.9 mu M, superior to ribavirin.
引用
收藏
页码:975 / 981
页数:7
相关论文
共 50 条
  • [41] Design, Synthesis, and Antiviral Activity of Novel Chalcone Derivatives Containing a Purine Moiety
    Gan, Xiuhai
    Wang, Yanjiao
    Hu, Deyu
    Song, Baoan
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (05) : 665 - 672
  • [42] Design, synthesis, anti-TMV activity, and preliminary mechanism of cinnamic acid derivatives containing dithioacetal moiety
    Wang, Yanju
    He, Fangcheng
    Wu, Sikai
    Luo, Yuqin
    Wu, Rong
    Hu, Deyu
    Song, Baoan
    PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2020, 164 : 115 - 121
  • [43] SYNTHESIS OF TODDACOUMAQUINONE, A COUMARIN-NAPHTHOQUINONE DIMER, AND ITS ANTIVIRAL ACTIVITIES
    ISHIKAWA, T
    KOTAKE, KI
    ISHII, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (06) : 1039 - 1041
  • [44] Design, Synthesis and Antiproliferative Activities of Artemisinin Derivatives Containing a Substituted Piperazine
    Yang, Xue-Lin
    Liu, Dan
    Wang, Wei
    Qu, Lei
    Jing, Yong-Kui
    Zhao, Lin-Xiang
    LETTERS IN DRUG DESIGN & DISCOVERY, 2009, 6 (08) : 595 - 598
  • [45] Design, Synthesis and Antibacterial Activities of Osthole Derivatives Containing Thiazole Fragment
    Yang, Jiaqiang
    Wu, Xuejiao
    Lu, Zicong
    Chen, Yangmi
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (11) : 3541 - 3549
  • [46] Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety
    Cui, Peipei
    Cai, Mingjiang
    Meng, Yanan
    Yang, Yan
    Song, Hongjian
    Liu, Yuxiu
    Wang, Qingmin
    SCIENTIFIC REPORTS, 2022, 12 (01)
  • [47] Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety
    Peipei Cui
    Mingjiang Cai
    Yanan Meng
    Yan Yang
    Hongjian Song
    Yuxiu Liu
    Qingmin Wang
    Scientific Reports, 12
  • [48] Design, synthesis and antifungal activities of novel pyrrole- and pyrazole-substituted coumarin derivatives
    Zhang, Shu-Guang
    Liang, Chao-Gen
    Sun, Yue-Qing
    Teng, Peng
    Wang, Jia-Qun
    Zhang, Wei-Hua
    MOLECULAR DIVERSITY, 2019, 23 (04) : 915 - 925
  • [49] Design, synthesis and antifungal activities of novel pyrrole- and pyrazole-substituted coumarin derivatives
    Shu-Guang Zhang
    Chao-Gen Liang
    Yue-Qing Sun
    Peng Teng
    Jia-Qun Wang
    Wei-Hua Zhang
    Molecular Diversity, 2019, 23 : 915 - 925
  • [50] Synthesis and antiviral, insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine, oxime or hydrazine moiety
    Li, Ling
    Li, Zheng
    Wang, Kailiang
    Liu, Yuxiu
    Li, Yongqiang
    Wang, Qingmin
    BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (03) : 474 - 483