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
Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination
黄志友 1杨平 1何波 2欧文霞 1袁思雨1
作者信息
- 1. 邵阳学院农林生态学院 湖南邵阳 422000
- 2. 南京农业大学植物保护学院 农作物生物灾害综合治理教育部重点实验室 南京 210095
- 折叠
摘要
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.
Abstract
In order to obtain novel abscisic acid analogues,morpholine-sulfonamide compound was designed under the prin-ciple 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 re-ceptor strongly than ABA and PM4.These results are benefit to discovering novel ABA analogues.
关键词
脱落酸功能类似物/吗啉磺酰胺化合物/抑制萌芽/芳基亲核取代反应Key words
ABA functional analogue/morpholine sulfonamide/inhibition germination/aromatic nucleophilic substitution引用本文复制引用
基金项目
湖南省自然科学基金青年基金(2021JJ40515)
湖南省教育厅优秀青年项目(21B0677)
出版年
2024
NETL
NSTL
万方数据