物理化学学报 >> 2010, Vol. 26 >> Issue (04): 1065-1074.doi: 10.3866/PKU.WHXB20100435

量子化学及计算化学 上一篇    下一篇

具有除草活性的大环内酯类衍生物的定量构效关系

段红霞, 王瑞刚, 张建军, 董燕红, 梁晓梅, 吴景平, 王道全   

  1. 中国农业大学应用化学系, 农业部农药化学与应用技术重点开放实验室, 北京 100193
  • 收稿日期:2009-11-27 修回日期:2010-01-25 发布日期:2010-04-02
  • 通讯作者: 梁晓梅, 王道全 E-mail:wangdq@cau.edu.cn; liangxiaomeim@yahoo.com.cn

QSAR of Macrolactone Derivatives with Herbicidal Activity

DUAN Hong-Xia, WANG Rui-Gang, ZHANG Jian-Jun, DONG Yan-Hong, LIANG Xiao-Mei, WU Jing-Ping, WANG Dao-Quan   

  1. Key Laboratory of Pesticide Chemistry and Application Technology, Ministry of Agriculture, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2009-11-27 Revised:2010-01-25 Published:2010-04-02
  • Contact: LIANG Xiao-Mei, WANG Dao-Quan E-mail:wangdq@cau.edu.cn; liangxiaomeim@yahoo.com.cn

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摘要：

研究了一系列结构新颖的具有除草活性的大环内酯衍生物的定量构效关系(QSAR). 构建的比较分子力场分析(CoMFA)、比较分子近似指数分析(CoMSIA)和全息定量构效关系(HQSAR)分子模型的交叉验证系数r2cv均大于0.5, 非交叉验证系数r2都超过0.8, 表明获取的QSAR模型具有可信的预测能力. 对CoMFA、CoMSIA模型的三维(3D)等势图分析, 发现除了立体场和静电场外, 疏水场和氢键受体场也是影响大环内酯类化合物除草活性的重要因素. 构建的HQSAR模型的原子贡献图提示的结构改造信息与三维QSAR的结果基本一致. 利用CoMFA、CoMSIA模型提供的信息,对目前已合成的活性最高化合物B1-3进行分子结构改造, 预测结果发现部分化合物可能具有更好的除草活性.

关键词: 比较分子力场分析, 比较分子近似指数分析, 全息定量构效关系, 大环内酯, 除草活性

Abstract:

We studied the quantitative structure-activity relationships (QSAR) of macrolactone derivatives. Statistical results fromthe established comparative molecular field analysis (CoMFA), the comparative molecular similarity indices analysis (CoMSIA), and the hologram quantitative structure-activity relationship (HQSAR) models showed believable predictability based on the cross-validated value (r2cv>0.5) and the non cross-validated value (r2>0.8). A contour maps analysis of the CoMFA and CoMSIA models showed that the hydrophobic and hydrogen-bond acceptor fields are important factors that affect the herbicidal activity of macrolactone compounds except for the steric and electrostatic fields. The structural modification information from the different atom contributions in the HQSAR model is in agreement with those of the 3D-QSAR models. According to the results from the CoMFA and CoMSIA models, the structure of compound B1-3 with the best herbicidal activity was modified and some designed compounds were predicted to have higher activity.

Key words: CoMFA, CoMSIA, HQSAR, Macrolactone, Herbicidal activity

MSC2000: 

  • O641