新型抗真菌先导物的合成和生物活性：3,5-二氯苄酯衍生物,Journal of Agricultural and Food Chemistry

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新型抗真菌先导物的合成和生物活性：3,5-二氯苄酯衍生物
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2021-12-20 , DOI: 10.1021/acs.jafc.1c04022
Shaoqing Du ₁ , Qinglong Yuan ₁ , Xueping Hu ₂ , Wen Fu ₁ , Qi Xu ₁ , Ziyi Wei ₁ , Jiazheng Xu ₁ , Xusheng Shao ₁ , Xuhong Qian _{1,

3}

Affiliation

琥珀酸脱氢酶（SDH）是开发新型杀菌剂最重要的分子靶点之一。羧酰胺杀菌剂是一类广泛用于抑制高破坏性植物病原体的SDH抑制剂。尽管近年来由于不受限制地使用而在真菌病原体中发现了抗药性的情况，但仍然需要具有改进的杀真菌活性的新化合物。因此，设计了一系列酯化合物来研究潜在的新型抗真菌分子。首先，不同苯甲醇化合物（A1-A21）的抗真菌活性) 进行了测试，发现了一个高活性片段（3,5-二氯苄醇）。随后，通过不同酸与3,5-二氯苯甲醇酯化合成了多种化合物，其中化合物5对灰葡萄孢和立枯丝核菌表现出显着的抗真菌活性，EC ₅₀值分别为6.60和1.61 mg/L，具有可比性商业杀菌剂啶酰菌胺 (EC ₅₀ = 1.24 和 1.01 mg/L)。体内试验进一步证明化合物5可有效抑制灰霉病（200 毫克/升，50.9%）。此外，SDH 抑制测定、荧光猝灭分析和线粒体膜电位的测定表明，化合物5具有与啶酰菌胺相似的作用。此外，目标化合物的杀真菌活性可以通过将酰胺键改性为酯键来保持。这些结果将为开发新型杀菌剂提供依据。

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Synthesis and Biological Activity of Novel Antifungal Leads: 3,5-Dichlorobenzyl Ester Derivatives

Succinate dehydrogenase (SDH) is one of the most important molecular targets for the development of new fungicides. Carboxamide fungicides are a class of SDH inhibitors widely used to inhibit highly destructive plant pathogens. Although cases of resistance have been found in fungal pathogens due to the unrestricted use in recent years, there is still demand for new compounds with improved fungicidal activity. Therefore, a series of ester compounds were designed to investigate potential novel antifungal molecules. First, the antifungal activity of different benzyl alcohol compounds (A1–A21) was tested, and a highly active fragment (3,5-dichlorobenzyl alcohol) was found. Subsequently, various compounds were synthesized by esterification between different acids and 3,5-dichlorobenzyl alcohol, among which compound 5 exhibited remarkable antifungal activity against Botrytis cinerea and Rhizoctonia solani with EC₅₀ values of 6.60 and 1.61 mg/L, respectively, which were comparable to those of commercial fungicide boscalid (EC₅₀ = 1.24 and 1.01 mg/L). In vivo testing further demonstrated that compound 5 was effective in suppressing B. cinerea (200 mg/L, 50.9%). Moreover, SDH inhibition assays, fluorescence quenching analysis, and determination of mitochondrial membrane potential revealed that compound 5 has similar effects to boscalid. Furthermore, the fungicidal activity of target compounds can be maintained by modifying the amide bond to an ester bond. These results will provide basis for the development of novel fungicides.

更新日期：2021-12-29

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