高等学校化学学报

高等学校化学学报

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苯砜基羧酸酯类急性毒性的QSAR研究

李吉来1, 杭烨超2, 耿彩云1, 黄旭日1, 李方实2, 孙家锺1   

    1. 吉林大学理论化学研究所， 理论化学计算国家重点实验室， 长春 130023;
    2. 南京工业大学理学院, 南京 210009
  • 收稿日期:2006-03-23 修回日期:1900-01-01 出版日期:2007-01-10 发布日期:2007-01-10
  • 通讯作者: 黄旭日

QSAR Study of Acute Toxicities of Phenylsulfonyl Carboxylate Compounds

LI Ji-Lai1, HANG Ye-Chao2, GENG Cai-Yun1, HUANG Xu-Ri1, LI Fang-Shi2, SUN Chia-Chung1   

    1. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130023, China;
    2. College of Science, Nanjing University of Technology, Nanjing 210009, China
  • Received:2006-03-23 Revised:1900-01-01 Online:2007-01-10 Published:2007-01-10
  • Contact: HUANG Xu-Ri

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被引次数

51

摘要： 采用密度泛函理论方法, 在B3LYP/6-31G(d)理论水平下, 计算了56种苯砜基羧酸酯类化合物的量子化学参数. 计算结果表明， 酯基连接的烷烃链亲水性越小, 毒性越大; 苯环连接的取代基亲水性越大, 毒性越大; 分子的体积越大, 毒性越小; 分子产生氢键的能力越大, 毒性越小; 分子最高占据轨道能量越高, 毒性越大.

关键词: 苯砜基羧酸酯, 急性毒性, 密度泛函, QSAR

Abstract: Based on the theoretical linear solvation energy relationship(LSER) parameters, a new QSAR model was established to correlate the acute toxicities of 56 phenylsulfonyl carboxylate compounds. All the descriptors were derived from quantum chemical computation at B3LYP/6-31G(d) level of theory. Compared with the model from TLSER, the new model has a better expression and prediction because more samples have been used. The model is shown below and its adequacy is R=0.94, R2adj=0.88, F=61.62, q2=0.83.
-lgEC50=a×EHOMO+b×P+c×q10+d×q1+e×μ+f×qH+costant
The computation results show that the smaller of the hydrophilicity of the substituent at the ester group, the bigger the acute toxicity; the bigger the hydrophilicity of the substitute attached to the benzene ring, the bigger the acute toxicity; the bigger the volume of the molecule, the smaller the toxicity; the bigger the ability of the molecule to form H-bonding, the smaller the toxicity; the higher the energy of HOMO, the bigger the toxicity. The present study may be helpful for probing the mechanism of action in acute toxicity of phenylsulfonyl carboxylate compounds and understanding the phenylsulfonyl carboxylate chemistry.

Key words: Phenylsulfonyl acetate, Acute toxicity, Density function theory, QSAR

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