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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (04): 399-404. 上一篇    下一篇

研究论文

1-取代-2-氨基苯并咪唑衍生物的理论计算及QSAR研究

谢湖均1,2，雷群芳*,1，胡晓环1，宣贵达3，方文军1   

  1. (1浙江大学化学系 杭州 310027)
    (2浙江工商大学应用化学系 杭州 310035)
    (3浙江大学城市学院药学系 杭州 310015)
  • 投稿日期:2010-05-12 修回日期:2010-09-15 发布日期:2010-10-21
  • 通讯作者: 雷群芳 E-mail:qflei@zju.edu.cn
  • 基金资助:

    人CYP转基因细胞系介导氨基氮杂环药物代谢的热动力学;神经胶质细胞仿生培养的表面效应和热化学;甜味受体蛋白三维结构及甜味识别机理模拟研究;甜味产生机理的理论研究;黄酮类抗氧化剂机理的理论研究和新型抗氧化剂的设计

Theoretical Calculations on 1-Substituted-2-aminobenzimidazole Derivatives and Studies on Quantitative Structure-activity Relationship (QSAR)

Xie Hujun1,2 Lei Qunfang*,1 Hu Xiaohuan1 Xuan Guida3 Fang Wenjun1   

  1. (1 Department of Chemistry, Zhejiang University, Hangzhou 310027)
    (2 Department of Applied Chemistry, Zhejiang Gongshang University, Hangzhou 310035)
    (3 Department of Pharmaceutical Sciences, Zhejiang University City College, Hangzhou 310015)
  • Received:2010-05-12 Revised:2010-09-15 Published:2010-10-21
  • Contact: Qun-Fang LEI E-mail:qflei@zju.edu.cn

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1600

被引次数

16

在B3LYP/6-31＋g(d)计算水平下, 通过运用密度泛函理论(DFT)量子化学方法, 对7种1-取代-2-氨基苯并咪唑衍生物的电子结构特征进行了研究, 获得了它们的电离能、亲合能、化学硬度、化学软度、化学势、电负性、亲电性、分配系数、折射率、极化率、分子体积和分子表面积等参数. 结果表明, 在2-氨基苯并咪唑衍生物的1位引入取代基团, 对化合物的电荷布居和结构性质都有较大的影响|关联了定量结构-活性关系(QSAR), 7种化合物的半数致死量LD50与极化率等有较好的相关性. 这些结果可为1-取代-2-氨基苯并咪唑衍生物的氧化代谢实验研究和毒性机理揭示等提供重要信息.

关键词: 1-取代-2-氨基苯并咪唑衍生物, 密度泛函理论(DFT), 自然键轨道方法(NBO), 生物毒性, 定量结构-活性关系(QSAR)

The quantum chemical calculation of density functional theory (DFT) has been performed to investigate the electronic structure and properties of seven derivatives of 1-substituted-2-aminobenzimidazole. The structural parameters and physical properties including vertical ionization potential, vertical electron affinity, chemical hardness, chemical softness, chemical potential, electronegativity, electronphilicity, partition coefficient, refractivity, polarizability, molecular volume and surface area are obtained. The calculations show that the substituted groups in 2-aminobenzimidazole molecules have significant effects on the charge populations and structural properties of the derivatives. On the basis of quantitative structure-activity relationship (QSAR) analysis, the values of biological toxicity LD50 for the compounds are well correlated with the polarizability. The results present important information for the experimental investigations on the oxidation metabolism and toxic mechanism of 1-substituted-2-aminobenzimidazole derivatives.

Key words: 1-substituted-2-aminobenzimidazole derivatives, density functional theory (DFT), natural bond orbital (NBO), biological toxicity, quantitative structure-activity relationship (QSAR)