Coumarin derivatives containing the 1,3,4 oxadiazole/thiadiazole moiety discovered as potential anti-tobacco mosaic virus agents.

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED Molecular Diversity Pub Date : 2025-01-20 DOI:10.1007/s11030-024-11098-y

Yuzhi Hu, Zhiling Sun, Wei Zeng, Yujiao Qiu, Zhiyuan Xu, Jing Zhang, Gang Feng

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Abstract

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 EC₅₀ values of 180.7, 190.3 and 215.8, 218.6 μg/mL, respectively, surpassing the efficacy of NingNanmycin, which exhibited EC₅₀ 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.

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含有1,3,4恶二唑/噻二唑片段的香豆素衍生物被发现为潜在的抗烟草花叶病毒剂。

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NMR和HRMS对其进行了表征。抗病毒活性评价表明，部分合成的化合物对烟草花叶病毒（TMV）具有较好的体内抗病毒作用。值得注意的是，化合物H6和Y5对TMV具有良好的治疗和保护作用，其EC50值分别为180.7、190.3和215.8、218.6 μg/mL，超过了宁南霉素的284.1和247.1 μg/mL。初步机制研究表明，H6和Y5对烟草花叶病毒衣壳蛋白（TMV- cp）具有较高的结合亲和力，可能阻碍TMV颗粒的自组装和复制过程。烟草叶片叶绿素含量和超氧化物歧化酶（SOD）活性升高，丙二醛（MDA）含量降低。H6有潜力被开发为一种新型抗病毒药物。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;