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Design, Synthesis, and Bioactivity of Novel Coumarin-3-carboxylic Acid Derivatives Containing a Thioether Quinoline Moiety

文献类型： 外文期刊

作者： Zhang, Yuanquan 1 ; Xu, Zhiyuan 2 ; Dou, Minxiang 2 ; Xu, Yan 2 ; Fu, Xin 2 ; Zhu, Fadi 2 ; Ye, Huochun 2 ; Zhang, Jing 2 ; Feng, Gang 2 ;

作者机构： 1.Guizhou Univ, Ctr R&D Fine Chem, Natl Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China

2.Chinese Acad Trop Agr Sci, Environm & Plant Protect Inst, Haikou 571101, Peoples R China

期刊名称：ACS OMEGA （ 影响因子：4.3； 五年影响因子：4.4 ）

ISSN： 2470-1343

年卷期： 2024 年 9 卷 51 期

页码：

收录情况： SCI

摘要： A series of coumarin-3-carboxylic acid derivatives containing a thioether quinoline moiety were designed and synthesized. The structures of these compounds were determined using 1H NMR, 13C NMR, and HRMS. The antibacterial activity of the compounds was evaluated against Xanthomonas oryzae pv oryzae (Xoo), Ralstonia solanacearum (Rs), and Acidovorax citrulli (Aac). The results showed that most of the compounds exhibited significant antibacterial activity against these pathogens. Particularly, compound A9 demonstrated potent activity against Xoo and Aac, with EC50 values of 11.05 and 8.05 mu g/mL respectively. In addition, A9 indicated strong protective and curative effects against Aac in vivo, with efficacy rates of 61.50 and 54.86%, respectively, surpassing those of the positive control thiodiazole copper. The scanning electron microscopy observations revealed that treatment of Aac cells with A9 at a concentration of 2EC50 resulted in a curved and sunken cell morphology, along with destroyed cell membrane integrity. Additionally, the motility and exopolysaccharide production of Aac were inhibited, and biofilm formation was prevented. Consequently, these newly developed derivatives of coumarin-3-carboxylic acid, incorporating the thioether quinoline moiety, hold promise as potential templates for the development of innovative antibacterial agents.

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