含氨基甲酸酯基团的新型丹皮酚衍生物的设计、合成、抗卵菌及抗真菌活性
Design, synthesis, anti-oomycete, and anti-fungal activities of novel paeonol derivatives containing carbamate moiety.
摘要(中文译文)
丹皮酚是中药牡丹根皮中的主要活性成分。为发现高效、广谱的农药生物活性新化合物，通过巧妙引入氨基甲酸酯药效团，设计并合成了20个新型丹皮酚氨基甲酸酯衍生物（1a-c、2a-c、3a-c、4a-c、5a-c和1-5dd'），其结构经1H NMR、13C NMR和HRMS充分表征。两个目标化合物2c和3c的立体化学构型通过单晶X射线衍射得以明确。此外，我们评价了这些目标化合物作为抗卵菌和抗真菌剂对两种严重农业病原菌——辣椒疫霉（Phytophthora capsici）和禾谷镰刀菌（Fusarium graminearum）的生物活性。在评价的化合物中：(1) 七个目标化合物2a、2b、3b、4b、5a、5b和5dd'对植物病原菌P. capsici表现出良好的抗卵菌活性。(2) 三个目标化合物5b、5c和5d,d'对植物病原菌F. graminearum表现出良好的抗真菌活性。(3) 当X = Y = Br且R = R = Et时，相应化合物5b表现出最佳的抗卵菌和抗真菌活性，EC值分别为79.03 mg/L和42.59 mg/L。此外，还观察到一些有趣的构效关系结果。本研究为进一步探索丹皮酚氨基甲酸酯衍生物的制备及农药生物活性提供了有价值的设计思路和理论数据。
Abstract
Paeonol is the main active ingredient in the Chinese medicinal herb peony root bark. In order to discover new compounds with high efficiency and broad-spectrum pesticide biological activity, twenty novel paeonol carbamate derivatives (1a-c, 2a-c, 3a-c, 4a-c, 5a-c, and 1-5dd') were designed and synthesized by ingeniously introducing carbamate pharmacophores, and their structures were well characterized by H NMR, C NMR, and HRMS. The stereochemical configurations of two target compounds 2c and 3c were unambiguously subjected to single-crystal X-ray diffraction. Moreover, we evaluated the bioactivities of these target compounds as anti-oomycete and anti-fungal agents against two serious agricultural pathogens, Phytophthora capsici and Fusarium graminearum. Amongst evaluated compounds, (1) Seven target compounds 2a, 2b, 3b, 4b, 5a, 5b, and 5dd' exhibited good anti-oomycete against the plant pathogen P. capsici. (2) Three target compounds 5b, 5c, and 5d,d' displayed good anti-fungal against the plant pathogen F. graminearum. (3) When X = Y = Br and R = R = Et, the corresponding compound 5b exhibits the best anti-oomycete and anti-fungal activity, with EC values of 79.03 mg/L and 42.59 mg/L, respectively. Moreover, some interesting results of structure-activity relationships were also observed. This study provides valuable design ideas and theoretical data for further exploring the preparation and pesticide biological activity of paeonol carbamate derivatives.
如何引用
AMA
Zimeng Fan, Yihao Guo, Jiaxuan He, Huan Liu, Genqiang Chen, Xiaobo Huang, et al. Design, synthesis, anti-oomycete, and anti-fungal activities of novel paeonol derivatives containing carbamate moiety.. Bioorganic chemistry. 2026; doi:10.1016/j.bioorg.2026.110404.
APA
Zimeng Fan, Yihao Guo, Jiaxuan He, Huan Liu, Genqiang Chen, Xiaobo Huang, et al (2026). Design, synthesis, anti-oomycete, and anti-fungal activities of novel paeonol derivatives containing carbamate moiety.. Bioorganic chemistry. https://doi.org/10.1016/j.bioorg.2026.110404
GB/T 7714
Zimeng Fan, Yihao Guo, Jiaxuan He, Huan Liu, Genqiang Chen, Xiaobo Huang, et al. Design, synthesis, anti-oomycete, and anti-fungal activities of novel paeonol derivatives containing carbamate moiety.[J]. Bioorganic chemistry, 2026 doi:10.1016/j.bioorg.2026.110404.
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