吗啉磺酰胺化合物的设计、合成及其抑制大豆萌芽活性的研究
收稿日期: 2023-07-15
修回日期: 2023-08-19
网络出版日期: 2023-09-28
基金资助
湖南省自然科学基金青年(2021JJ40515); 湖南省教育厅优秀青年(21B0677)
Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination
Received date: 2023-07-15
Revised date: 2023-08-19
Online published: 2023-09-28
Supported by
Natural Science Foundation of Hunan Province Youth Project(2021JJ40515); Scientific Research Fund of Hunan Provincial Education Department(21B0677)
为了发现新型脱落酸功能类似物, 采用活性亚结构拼接原理设计了含吗啉磺酰胺片段的目标分子. 以吗啉-4-磺酰胺和氟代硝基苯为起始原料, 经芳基亲核取代反应合成了14个目标化合物, 该合成方法操作简单, 底物适用范围广. 种子萌芽实验结果表明, 浓度为50 µmol/L时4a~4d、4k、4m、4n等7个化合物处理后完全抑制萌芽, 25 µmol/L时4a~4d、4k、4m、4n等7个化合物处理后抑制率仍高于95%. 进一步降低至15 μmol/L时, 发现4m、4n的抑制活性高于ABA和先导化合物PM4. 分子对接结果表明, 引入吗啉促使小分子中磺酰基(SO2)与Ser98形成氢键, 提高了结合受体的能力, 所以4m和4n的打分函数高于ABA和PM4, 活性也更高. 该结果有利于发现新型脱落酸功能类似物.
黄志友 , 杨平 , 何波 , 欧文霞 , 袁思雨 . 吗啉磺酰胺化合物的设计、合成及其抑制大豆萌芽活性的研究[J]. 有机化学, 2024 , 44(1) : 309 -315 . DOI: 10.6023/cjoc202307014
In order to obtain novel abscisic acid analogues, morpholine-sulfonamide compound was designed under the principle of active substructure combination. 14 target compounds were obtained through aromatic nucleophilic substitution (SNAr) when fluoride nitrobenzene and morpholine-4-sulfonamide were used as starting materials. The approach represents simple operation and broad substrate scope. Additionally, the soybean seed germination was inhibited overwhelmingly when treated with compounds 4a~4d, 4k, 4m and 4n at 50 μmol/L. Furthermore, the inhibition activity of compounds 4a~4d, 4k, 4m and 4n was higher than 95% at 25 μmol/L. Finally, the activity of 4m and 4n was much higher than that of ABA and lead compound (PM4) at 15 μmol/L. Moreover, the molecular docking study revealed that 4m and 4n could bind abscisic acid receptor strongly than ABA and PM4. These results are benefit to discovering novel ABA analogues.
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