高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (11): 2031-2033.

• 研究论文 • 上一篇    下一篇

N-(4-取代嘧啶-2-基)苄基磺酰脲和苯氧基磺酰脲的3D-QSAR研究

马翼, 姜林, 李正名, 赖城明   

  1. 南开大学化学学院, 元素有机化学国家重点实验室, 农药国家工程研究中心, 天津300071
  • 收稿日期:2003-09-25 出版日期:2004-11-24 发布日期:2004-11-24
  • 基金资助:

    国家“九七三”计划(批准号:s2003CB114406);天津大学与南开大学联合研究项目资助

3D-QSAR Study on N-(4-Substituted pyrimidin-2-yl) Benzyl Sulfonylurea and Phenoxy Sulfonylurea

MA Yi, JIANG Lin, LI Zheng-Ming, LAI Cheng-Ming   

  1. State Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Resarch Center, College of Chemistry, Nankai Universsity, Tianjin 300071, China
  • Received:2003-09-25 Online:2004-11-24 Published:2004-11-24

摘要: 采用比较分子力场分析(CoMFA)方法,对两类单取代嘧啶类似物、6个N-(4-取代嘧啶-2-基)-2-甲氧羰基苄基磺酰脲(1a~1f)和14个N-(4-取代嘧啶-2-基)-2-取代苯氧基磺酰脲(2a~2n)进行三维定量构效关系(3D-QSAR)研究.建立了一个较为可靠的预测模型.结果表明,分子中苯环邻位、嘧啶环形成氢键的N原子处以及嘧啶环4位和6位附近负电荷增加;苯环邻位乙氧基的CH2CH3附近选择带正电的原子;苯环邻位乙氧基附近空间体积增加,而嘧啶环4位甲氧基稍远处取代基的立体位阻不超过此位置,将有利于提高活性.最后解释了修饰磺酰脲的除草剂仍具有较高活性的原因.

关键词: 比较分子力场分析, 三维定量构效关系, 磺酰脲化合物, 除草活性

Abstract: Comparative molecular field analysis(CoMFA) method was applied to the study of the three-dimensional quantitative structure activity relationship(3D-QSAR) on two series of N-(4-substituted pyrimidin-2-yl)-2-methyl carboxylate-benzyl sulfonylureas and N-(4-substituted pyrimidin-2-yl)-2-substituted phenoxy sulfonylureas. A reasonable model with predictive ability was obtained from the investigation. According to the resulting contour map of electrostatic field, compounds with enhanced activity could be designed by introduction of more negative charged group into the red region, and positive charged substituent in the blue region will lead to more herbicidal activity. For the steric field, the introduction of smaller groups into the yellow region gives a compound with a higher activity and larger groups in the green region will improve the activity. The models were used to explain why the sulfonylureas with a modified bridge still remain a high herbicidal activity and will help us in our further study.

Key words: CoMFA, 3D-QSAR, Sulfonylurea compound, Herbicidal activity

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