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4，5，6-三取代嘧啶苯磺酰脲类化合物的生物活性、分子对接与3D—QSAR关系研究
  • ISSN号：0567-7351
  • 期刊名称：《化学学报》
  • 时间：0
  • 分类：TQ457.29[化学工程—农药化工] TQ463[化学工程—制药化工]
  • 作者机构：[1]南开大学元素有机化学研究所元素有机化学国家重点实验室,天津300071
  • 相关基金：国家自然科学基金（No.20432010）和天津市应用基础研究计划（No.07JCYBJC00200）资助项目.
作者： 郭万成[1], 马翼[1], 李永红[1], 王素华[1], 李正名[1]
关键词： 分子对接, 乙酰羟酸合成酶, 比较分子相似性指数分析, 三维定量构效关系, 三取代嘧啶苯磺酰脲, 除草活性, molecular docking, AHAS, CoMSIA, 3D-QSAR, N-（trisubstituted pyrimidin-2-yl）-N′-benzenesulfonylurea, herbicidal activity
中文摘要：

用柔性分子对接方法（FlexX）将15个4，5，6-兰取代嘧啶苯磺酰脲化合物以及3个不含5-位取代嘧啶苯磺酰脲化合物（分别为4,6-双取代嘧啶和4-取代嘧啶）和乙酰羟酸合成酶（AHAS）活性口袋进行了对接，对接程序预测的抑制剂和酶之间的相互作用能与抑制活性之间有一定的相关性，相关系数为0．660．然后采用比较分子相似性指数分析（CoMSIA）对27个新型4，5，6-二取代嘧啶苯磺酰脲类化合物的除草活性进行三维定量构效关系（3D-QSAR）研究．建立了三维定量构效关系CoMSIA模型，立体场、静电场和氢键的贡献分别为47.3％，32．8％，19．9％．交叉验证系数q^2值为0．520．根据CoMSIA模型的立体场、静电场、氢键给体场三维等值线图不仅直观地解释了结构与活性的关系，并且与用Flexx预测的结合模式相一致．证明了我们预测的结合模式是可靠的，为进一步设计高活性的标题化合物提供较好的理论指导．

英文摘要：

Fifteen N-（4,5,6-trisubstituted pyrimidin-2-yl）-N′-benzenesulfonylureas and three analogous benzenesulfonylureas without 5-substituent at pyrimidine moiety were studied on a flexing molecular docking method （flexX） according to their biological activity to the active site of acetohydroxyacid synthase （AHAS）. The predicted binding affinities of the molecules were found to be linearly relevant to their experimental activities （R=0.660）. Then 27 N-（4,5,6-trisubstituted pyrimidin-2-yl）-N′-benzenesulfonylureas were studied on comparative molecular similarity index analysis. The results showed that the contribution of 2 steric, electrostatic and H-bond donor was 47.3%, 32.8% and 19.9%, respectively. The cross-validated q was 0.520. The results indicate that the 3D-QSAR model is significant and has good predictability, providing useful information for designing new good activity AHAS inhibitors prior to their synthesis.

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期刊信息
  • 《化学学报》
  • 北大核心期刊（2014版）
  • 主管单位:中国科学院
  • 主办单位:中国化学会 中国科学院上海有机化学研究所
  • 主编：周其林
  • 地址：上海市零陵路345号
  • 邮编：200032
  • 邮箱：hxxb@sioc.ac.cn
  • 电话：021-54925085
  • 国际标准刊号：ISSN：0567-7351
  • 国内统一刊号：ISSN：31-1320/O6
  • 邮发代号:4-209
  • 获奖情况:
  • 首届国家期刊奖,第二届国家期刊奖提名奖,中国期刊方阵“双高期刊”
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘（网络版）,荷兰文摘与引文数据库,美国科学引文索引（扩展库）,日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊（2004版）,中国北大核心期刊（2008版）,中国北大核心期刊（2011版）,中国北大核心期刊（2014版）,英国英国皇家化学学会文摘,中国北大核心期刊（2000版）
  • 被引量:28694