Design, synthesis, X-ray crystal structure and antibacterial activity of ferulic acid derivatives bearing sulfonamide moiety

IF 1.4 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2025-07-03 DOI:10.1080/10426507.2025.2517257

Song Bai (Conceptualization Funding acquisition Investigation Resources Supervision Writing – review & editing) , Suran Wan (Conceptualization Funding acquisition Investigation Methodology Resources Writing – original draft Writing – review & editing) , Rong Wu (Conceptualization Investigation Methodology Resources) , Miao Li (Conceptualization Data curation Investigation Methodology) , Fang Wang (Conceptualization Investigation Methodology) , Shouying Tang (Conceptualization Investigation Methodology) , Lijun Chen (Conceptualization Data curation Investigation Project administration) , Xian Wei (Conceptualization Investigation) , Shuang Feng (Conceptualization Investigation) , Miaohe Zhang (Conceptualization Investigation)

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引用次数: 0

Abstract

A total of 28 new ferulic acid derivatives bearing the sulfonamide moiety were designed and synthesized, followed by an evaluation of their antibacterial activities. The structures of the synthesized compounds (B1 − B28) were fully characterized using ¹H NMR,¹³C NMR, and HRMS techniques. Among them, the structure of compound B11 was further elucidated through X-ray single-crystal diffraction analyses. Bioassay results indicated that several target compounds exhibited significant inhibitory activity against the tested plant pathogens in vitro. Notably, compound B28 demonstrated the highest resistance to Xanthomonas oryzae pv. oryzicola (Xoc), with an EC₅₀ (half-maximal effective concentration) value of 28.6 μg/mL, which was more than twice as effective as the control agents zinc thiazole (EC₅₀ = 74.4 μg/mL) and thiodiazole copper (EC₅₀ = 97.1 μg/mL). Mechanistic studies revealed that B28 enhances bacterial membrane permeability and disrupts cell morphology. This work highlights promising candidates for agricultural antibacterial applications.

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含磺胺片段阿魏酸衍生物的设计、合成、x射线晶体结构及抗菌活性

设计合成了28个含磺胺基团的阿魏酸衍生物，并对其抑菌活性进行了评价。利用1H NMR、13C NMR和HRMS技术对合成的化合物（B1−B28）进行了结构表征。其中，化合物B11的结构通过x射线单晶衍射分析得到了进一步的阐明。生物实验结果表明，几种目标化合物对植物病原菌具有明显的体外抑制活性。值得注意的是，化合物B28对水稻黄单胞菌的抗性最高。oryzicola （Xoc）的EC50（半最大有效浓度）值为28.6 μg/mL，是对照剂噻唑锌（EC50 = 74.4 μg/mL）和噻唑铜（EC50 = 97.1 μg/mL）的2倍以上。机制研究表明B28增强细菌膜通透性，破坏细胞形态。这项工作突出了农业抗菌应用的有前途的候选者。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.