Synthesis, Antifungal Activity, and 3D-QASR of Novel 1,2,3,4-Tetrahydroquinoline Derivatives Containing a Pyrimidine Ether Scaffold as Chitin Synthase Inhibitors

文献类型： 外文期刊

第一作者： Zhang, Xiaoming

作者： Zhang, Xiaoming;Yang, Zhaokai;Xu, Huan;Yang, Xinling;Sun, Tengda;Lu, Xingxing;Shi, Fasheng;Duan, Hongxia;Ling, Yun;Liu, Yuansheng;Yang, Qing;Chen, Wei

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关键词： 1,2,3,4-tetrahydroquinoline; pyrimidine ether scaffold; antifungal activity; 3D-QSAR; chitin synthase inhibitors

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.895； 五年影响因子：6.048 ）

ISSN： 0021-8561

年卷期： 2022 年 70 卷 30 期

页码：

收录情况： SCI

摘要： The introduction of active groups of natural products into the framework of pesticide molecules is an effective approach for discovering active lead compounds, and thus has been widely used in the development of new agrochemicals. In this work, a novel series of 1,2,3,4-tetrahydroquinoline derivatives containing a pyrimidine ether scaffold were designed and synthesized by the active substructure splicing method. The new compounds showed good antifungal activities against several fungi. Especially, compound 4fh displayed excellent in vitro activity against Valsa mali and Sclerotinia sclerotiorum with EC50 values of 0.71 and 2.47 mu g/mL, respectively. 4fh had slightly stronger inhibitory activity (68.08% at 50 mu M) against chitin synthase (CHS) than that of polyoxin D (63.84% at 50 mu M) and exhibited obvious curative and protective effects on S. sclerotiorum in vivo. Thus, 4fh can be considered as a new candidate fungicide as a chitin synthase inhibitor. An accurate and reliable three-dimensional quantitative structure-activity relationship (3D-QSAR) model presented a useful direction for the further excogitation of more highly active fungicides. Molecular docking revealed that the conventional hydrogen bond mainly affected the binding affinity of 4fh with chitin synthase. The present results will provide a guidance to discover potential CHS-based fungicides for plant disease control in agriculture.

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