含有1,3,4-恶二唑/噻二唑部分的香豆素衍生物被发现是潜在的抗烟草花叶病毒剂。
Coumarin derivatives containing the 1,3,4 oxadiazole/thiadiazole moiety discovered as potential anti-tobacco mosaic virus agents.
作者信息
Hu Yuzhi, Sun Zhiling, Zeng Wei, Qiu Yujiao, Xu Zhiyuan, Zhang Jing, Feng Gang
机构信息
State Key Laboratory of Green Pesticide, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China.
Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Haikou, 571101, China.
出版信息
Mol Divers. 2025 Jan 20. doi: 10.1007/s11030-024-11098-y.
In this paper, a series of oxadiazole/thidiazole containing coumarin derivative derivatives were designed, synthesized and characterized using NMR and HRMS. The evaluation of antiviral activity revealed that some of the synthesized compounds exhibited good in vivo antiviral efficacy against tobacco mosaic virus (TMV). Notably, compounds H6 and Y5 demonstrated exceptional therapeutic and protective effects against TMV, with EC values of 180.7, 190.3 and 215.8, 218.6 μg/mL, respectively, surpassing the efficacy of NingNanmycin, which exhibited EC values of 284.1 and 247.1 μg/mL. The preliminary mechanistic studies indicated that H6 and Y5 had ahigh binding affinity for the tobacco mosaic virus capsid protein (TMV-CP), potentially obstructing the self-assembly and replication processes of TMV particles. Furthermore, the chlorophyll content and superoxide dismutase (SOD) activity in tobacco leaves increased, while the malondialdehyde (MDA) content decreased. H6 has the potential to be developed as a novel antiviral.
本文设计、合成了一系列含恶二唑/噻二唑的香豆素衍生物，并利用核磁共振（NMR）和高分辨质谱（HRMS）对其进行了表征。抗病毒活性评估显示，部分合成化合物对烟草花叶病毒（TMV）表现出良好的体内抗病毒效果。值得注意的是，化合物H6和Y5对TMV展现出卓越的治疗和保护作用，其半数有效浓度（EC）值分别为180.7、190.3和215.8、218.6μg/mL，超过了宁南霉素的效果，宁南霉素的EC值为284.1和247.1μg/mL。初步机理研究表明，H6和Y5对烟草花叶病毒衣壳蛋白（TMV-CP）具有高结合亲和力，可能阻碍TMV粒子的自组装和复制过程。此外，烟草叶片中的叶绿素含量和超氧化物歧化酶（SOD）活性增加，而丙二醛（MDA）含量降低。H6有潜力被开发成为一种新型抗病毒剂。
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