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除草活性的构效关系.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.
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 die heterocycle and urea moiety; (b) carbonyl 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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2001年第11期810-815,共6页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金，国家自然科学基金
