Design, synthesis and antiviral activity of indole derivatives containing quinoline moiety.

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2024-07-24 DOI:10.1007/s11030-024-10894-w

Bangcan He, Yuzhi Hu, Yishan Qin, Yufang Zhang, Xingping Luo, Zhenchao Wang, Wei Xue

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Abstract

A series of indole derivatives containing quinoline structures were designed and synthesized. The synthesized compounds were characterized by NMR and HRMS. And W14 was performed by single crystal X-ray diffraction experiments. The antiviral activity studies showed that some of the target compounds possessed significant activity against tobacco mosaic virus (TMV). In particular, W20 had significant activity. The results of in vivo anti-TMV activity assay showed that W20 possessed the best curative and protective activities with EC₅₀ values of 84.4 and 65.7 μg/mL, which were better than ningnanmycin (NNM) 205.1 and 162.0 μg/mL, respectively. The results of Microscale thermophoresis (MST) showed that W20 had a strong binding affinity for the tobacco mosaic virus coat protein (TMV-CP) with a dissociation constant (K_d) of 0.00519 μmol/L, which was superior to that of NNM (1. 65320 μmol/L). The molecular docking studies were in accordance with the experimental results. In addition, the determination of malondialdehyde (MDA) content in tobacco leaves showed that W20 improved the disease resistance of tobacco. Overall, this study shows that indole derivatives containing quinoline can be used as new antiviral agents for plant viruses for further research.

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含喹啉分子的吲哚衍生物的设计、合成和抗病毒活性。

设计并合成了一系列含有喹啉结构的吲哚衍生物。合成的化合物通过核磁共振和 HRMS 进行了表征。通过单晶 X 射线衍射实验对 W14 进行了表征。抗病毒活性研究表明，一些目标化合物对烟草花叶病毒（TMV）具有显著的活性。其中，W20 具有显著的活性。体内抗TMV活性测定结果表明，W20具有最佳的治疗和保护活性，EC50值分别为84.4和65.7 μg/mL，分别优于宁南霉素（NNM）的205.1和162.0 μg/mL。微尺度热泳（MST）结果表明，W20与烟草花叶病毒衣壳蛋白（TMV-CP）具有很强的结合亲和力，其解离常数（Kd）为0.00519 μmol/L，优于宁南霉素（NNM）（1.65320 μmol/L）。分子对接研究结果与实验结果一致。此外，烟草叶片中丙二醛（MDA）含量的测定表明，W20 提高了烟草的抗病性。总之，本研究表明，含喹啉的吲哚衍生物可用作植物病毒的新型抗病毒剂，有待进一步研究。

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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;