Synthesis and Evaluation of Novel 1-Methyl-1H-pyrazol-5-amine Derivatives with Disulfide Moieties as Potential Antimicrobial Agents,Journal of Agricultural and Food Chemistry

当前位置： X-MOL 学术 › J. Agric. Food Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis and Evaluation of Novel 1-Methyl-1H-pyrazol-5-amine Derivatives with Disulfide Moieties as Potential Antimicrobial Agents
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-03 , DOI: 10.1021/acs.jafc.4c06431
Yantao Li ₁ , Yuxin Mu ₁ , Yuan Cao ₁ , Dan Xu _{1,

2} , Xili Liu _{1,

3} , Gong Xu _{1,

2}

Affiliation

Sulfur-containing compounds have diverse biological functions and are crucial in crop protection chemistry. In this study, a series of novel 1-methyl-1H-pyrazol-5-amine derivatives incorporating disulfide moieties were synthesized and evaluated for their antimicrobial properties. In vitro bioassays demonstrated that compound 7f displayed potent antifungal activity against Valsa mali, with an EC₅₀ value of 0.64 mg/L, outperforming allicin (EC₅₀ = 26.0 mg/L) but lower than tebuconazole (EC₅₀ = 0.33 mg/L). In vivo experiments confirmed that compound 7f could effectively inhibit V. mali infection on apples at a concentration of 100 mg/L, similar to the positive control tebuconazole. Mechanistic studies revealed that compound 7f could induce hyphal shrinkage and collapse, trigger intracellular reactive oxygen species accumulation, modulate antioxidant enzyme activities, initiate lipid peroxidation, and ultimately cause irreversible oxidative damage to the cells of V. mali. Additionally, compound 7b exhibited notable antibacterial activity, particularly against Pseudomonas syringae pv. actinidiae, with a MIC₉₀ value of 1.56 mg/L, surpassing the positive controls allicin, bismerthiazol, and streptomycin sulfate. These findings suggest that 1-methyl-1H-pyrazol-5-amine derivatives containing disulfide moieties hold promise as potent candidates for the development of novel antimicrobial agents.

中文翻译：

具有二硫键的新型1-甲基-1H-吡唑-5-胺衍生物作为潜在抗菌剂的合成与评价

含硫化合物具有多种生物功能，在作物保护化学中至关重要。在本研究中，合成了一系列包含二硫键的新型 1-甲基-1H-吡唑-5-胺衍生物，并评估了其抗菌特性。体外生物测定表明，化合物7f对Valsa mali表现出有效的抗真菌活性，EC ₅₀值为0.64 mg/L，优于大蒜素（EC ₅₀ = 26.0 mg/L），但低于戊唑醇（EC ₅₀ = 0.33 mg/L）。。体内实验证实，化合物7f在100 mg/L浓度下能有效抑制苹果V. mali感染，与阳性对照戊唑醇相似。机理研究表明，化合物7f可诱导菌丝收缩和塌陷，引发细胞内活性氧积累，调节抗氧化酶活性，引发脂质过氧化，最终对V. mali细胞造成不可逆的氧化损伤。此外，化合物7b表现出显着的抗菌活性，特别是针对丁香假单胞菌pv。猕猴桃的 MIC ₉₀值为 1.56 mg/L，超过阳性对照大蒜素、双噻唑和硫酸链霉素。这些发现表明，含有二硫化物部分的1-甲基-1H-吡唑-5-胺衍生物有望成为开发新型抗菌剂的有效候选者。

更新日期：2024-09-03

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南