Design, synthesis, and antibacterial activity of novel amide derivatives containing a sulfone moiety

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED Molecular Diversity Pub Date : 2025-02-11 DOI:10.1007/s11030-024-11088-0

Yue Zou, Xing Liu, Zongnan Zhu, Chao Zhang, Yong Zhang, Yuanzheng Zhao, Xiang Zhu, Jixiang Chen

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Abstract

Twenty-four amide compounds containing a sulfone moiety were synthesized and the antibacterial activity of the target compounds was tested. Some compounds show excellent antibacterial activity. For example, compound AC4 exhibited broad antibacterial activity with the EC₅₀ of 0.55 mg/L for Xanthomonas axonopodis pv. citr (Xac), and 0.48 mg/L for Xanthomonas oryzae pv. oryzae (Xoo). In the greenhouse, compound AC4 with a concentration of 200 mg/L had good protective activity (39.3%) and curative activity (42.2%) against bacterial leaf blight, both were superior to the commercial antibacterial thiodiazole-copper (19.2% and 31.8%) and bismerthiazol (27.4% and 23.1%). The compound AC4 can inhibit the normal growth of Xoo by inhibiting the virality factors of Xoo (motility, exopolysaccharides, and biofilms). At the same time, molecular docking results showed that compound AC4 could interact with exopolysaccharides and quorum sensing-related proteins. This result was further supported by relative gene expression analysis. In addition, the compound AC4 can also increase membrane permeability, induce intracellular reactive oxygen species (ROS) levels to rise, and cause the surface of Xoo to change. The compound AC4 can be further studied as a potential antibacterial agent and this structure will continue to be optimized.

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含有砜段的新型酰胺衍生物的设计、合成和抗菌活性。

合成了24个含砜的酰胺类化合物，并对其抑菌活性进行了测试。有些化合物具有良好的抗菌活性。例如，化合物AC4对axonopodis pv具有广泛的抑菌活性，EC50为0.55 mg/L。黄单胞菌（Xanthomonas oryzae pv） 0.48 mg/L。oryzae (Xoo语)。在温室中，浓度为200 mg/L的化合物AC4对细菌性叶枯病具有良好的保护活性（39.3%）和治疗活性（42.2%），均优于商品抗菌硫代二唑铜（19.2%和31.8%）和双硫代噻唑（27.4%和23.1%）。化合物AC4可以通过抑制Xoo的病毒因子（运动性、胞外多糖和生物膜）抑制Xoo的正常生长。同时，分子对接结果表明，化合物AC4可与胞外多糖和群体感应相关蛋白相互作用。相关基因表达分析进一步支持了这一结果。此外，化合物AC4还能增加膜通透性，诱导细胞内活性氧（ROS）水平升高，引起Xoo表面变化。化合物AC4作为一种潜在的抗菌剂可以进一步研究，其结构将继续优化。

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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;