Discovery of novel pyridine carboxamides with antifungal activity as potential succinate dehydrogenase inhibitors.

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Journal of Pesticide Science Pub Date : 2022-08-20 DOI:10.1584/jpestics.D22-017
Zhongzhong Yan, Zihui Yang, Longjian Qiu, Yan Chen, Aijun Li, Taopeng Chang, Xinzhe Niu, Jingyan Zhu, Shihao Wu, Feng Jin
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Abstract

Fifteen novel pyridine carboxamide derivatives bearing a diarylamine-modified scaffold were designed, synthesized, and their antifungal activity was evaluated. Preliminary bioassay results showed that some of the synthesized compounds exhibited moderate to good in vitro antifungal activity. Further, compound 6-chloro-N-(2-(phenylamino)phenyl)nicotinamide (3f) displayed good in vivo antifungal activity against Botrytis cinerea. The enzymatic test on B. cinerea succinate dehydrogenase (SDH) showed that the inhibitory activity possessed by compound 3f equally matches that of thifluzamide. Molecular docking results demonstrated that compound 3f could commendably dock with the active site of SDH via stable hydrogen bonds and hydrophobic interactions, suggesting the possible binding modes of the title compounds with SDH. The results above revealed that the target compounds would be the leading fungicide compound for further investigation.

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具有抗真菌活性的新型吡啶类羧胺类琥珀酸脱氢酶抑制剂的发现。
设计、合成了15种新型二芳胺修饰吡啶羧胺衍生物,并对其抗真菌活性进行了评价。初步的生物试验结果表明,部分合成的化合物具有中等到良好的体外抗真菌活性。此外,化合物6-氯- n -(2-(苯基氨基)苯基)烟酰胺(3f)在体内对灰霉病菌具有良好的抗真菌活性。酶学试验表明,化合物3f对葡萄球菌琥珀酸脱氢酶(SDH)的抑制活性与硫氟唑胺相当。分子对接结果表明,化合物3f可以通过稳定的氢键和疏水相互作用与SDH活性位点很好地对接,提示了标题化合物与SDH可能的结合方式。上述结果表明,目标化合物将是进一步研究的主要杀菌剂化合物。
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来源期刊
Journal of Pesticide Science
Journal of Pesticide Science 农林科学-昆虫学
CiteScore
4.30
自引率
4.20%
发文量
28
审稿时长
18-36 weeks
期刊介绍: The Journal of Pesticide Science publishes the results of original research regarding the chemistry and biochemistry of pesticides including bio-based materials. It also covers their metabolism, toxicology, environmental fate and formulation.
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