Zimeng Fan, Yihao Guo, Jiaxuan He, Huan Liu, Genqiang Chen, Xiaobo Huang, Yuee Tian, Lin Zhou, Zhiping Che
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引用次数: 0
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 1H NMR, 13C 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 R1 = R2 = Et, the corresponding compound 5b exhibits the best anti-oomycete and anti-fungal activity, with EC50 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.
期刊介绍：
Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry.
For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature.
The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.
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