新磺酰脲类除草活性构效关系的研究 |
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引用本文: | 李正名,赖城明. 新磺酰脲类除草活性构效关系的研究[J]. 有机化学, 2001, 21(11): 810-815 |
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作者姓名: | 李正名 赖城明 |
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作者单位: | 南开大学化学学院, |
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基金项目: | 国家自然科学重点基金(Nos.29232010,29832050)和国家自然科学基金(Nos.29322001,29772019)资助项目 |
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摘 要: | 磺酰脲类除草剂具有对环境友好和超高效的特点。本文采用X-衍射谱对其绝对构型进行分析,首次发现分子内氢键的存在。采用各种理论和软件计算,活性结构应符合三点要求:(a)分子内氢键使杂环和脲之间形成一个共轭体系;(b)羰基氧、磺酰氧和杂环氮形成分子中三个负电中心;(c)在磺酰胺与苯邻位取代基之间形成一个空穴。根据以上结论,构建了一个卡口模型,较合理地解释了磺酰脲类草活性的构效关系。建立了一个虚拟靶酶ALS的模拟作用模型,供进一步分子设计ALS抑制剂,包括一些非磺酰脲类先导化合物时参考。
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关 键 词: | 磺酰脲类 分子设计 乙酰乳酸合成酶 分子内 氢键 构效关系 生物活性 除草剂 |
修稿时间: | 2001-08-20 |
Research on the structure/activity relationship of herbicidal sulfonylureas |
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Affiliation: | Nankai Univ., Coll Chem.Tianjin(300071) |
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Abstract: | Some sulfonylureas are an important class of environmental benign, ultra-low dosage herbicides. X-ray diffraction spectra of bio-active sulfonylureas were carefully examined and an intra-molecular hydrogen bond was first reported here. By theoretical calculation, three essential structural requirements for the bio-activity were concluded as follows: (a) all intramolecular hydrogen bonds cause a coplanar conjugated system between the heterocycle and urea moiety; (b) carbomyl oxygen, sulfonyl oxygen and heterocyclic nitrogen form three negative centers; (c) between sulfonylamido and phenyl ortho substituent, there is a cavity. A Caliper model thus deduced reasonably explains the structure/activity relationship of bioactive sulfonylureas. A 3-D contour map of a pseudo-ALS model was set up with which could lead to further design of novel ALS inhibitors, including some possible non-sulfonylureas leads. |
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Keywords: | SULFONYLUREA MOLECULAR DESIGN INTRAMOLECULARLY HYDROGEN BONDS STRUCTURE ACTIVITY RELATIONSHIP BIOLOGICAL ACTIVITY HERBICIDES |
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