|Table of Contents|

Retention Indexes Prediction of Chiral Organic Acids Using Chiral Connectivity Indices

《南京理工大学学报》(自然科学版)[ISSN:1005-9830/CN:32-1397/N]

Issue:
2012年02期
Page:
359-363
Research Field:
Publishing date:

Info

Title:
Retention Indexes Prediction of Chiral Organic Acids Using Chiral Connectivity Indices
Author(s):
TANG Zi-qiang12FENG Chang-jun1
1.School of Chemistry and Chemical Engineering,Xuzhou Institute of Technology,Xuzhou 221008,China; 2.Xuzhou Technical Institute,Xuzhou 221151,China
Keywords:
hydroxyl acids amino acids retention indexes molecular connectivity indexes chiral indexes quantitative structure-retention index relationship
PACS:
TQ460.72;O212.1
DOI:
-
Abstract:
A better chiral connectivity index mcXtv is obtained by extending the molecular connectivity index mXtv.The new indice mcXtv can describe the chiral information of chiral molecules.The quantitative structure-retention index relationship(QSRR)between mcXtv and the thin-layer chromatogram retention index-RM of 18 chiral organic acids(8 hydroxyl acids and 10 amino acids)is investigated with the multivariate statistical regression.The optimal two-parameter QSRR model is set up by leaps-and-bounds regression analysis,and its traditional correlation coefficient R2 and the cross-validation correlation coefficient Q2 of leave-one-out(LOO)are 0.915 and 0.878 respectively.The results show that the model from extended topological indices has good reliability and predictive ability and is better than that of Kier ’ s connectivity indices.From the two chiral connectivity indices 0cXvp,4cXvpc,it can be seen that the two-dimensional structure and the chiral characteristics of the molecular are the decisive factors affecting the the retention index of the chiral organic acids.The results show that the parameter mcXtv is rational and efficient for representing the retention indexes of the chiral organic acids.

References:

[1] 孙璐,杨亚楠,严静. 手性药物的立体选择性药物动力学[J]. 中国药物化学杂志, 2009, 19( 6) : 498-451.
[2] 王杰,刘焕香,司宏宗,等. 基于定量结构-性质关系方法预测氨基酸的比旋光度[J]. 分析化学,2006, 34( 12) : 1759-1762.
[3] 王俊,许禄. 手性分子与手性拓扑指数[J]. 高等学校化学学报, 2007, 28( 1) : 46-48.
[4] Díaz H G,Snchez I H,Uriarte E, et al. Symmetry considerations in Markovian chemicals ‘inilico’design ( March-inside) Ⅰ: central chirality codification, classification of ACE inhibitors and prediction of s-receptor antagonist activities[J]. Comput Biol Chem,2003,27 ( 3) : 217-227.
[5] Ponce Y M,Díaz H G,Zaldivar V R,et al. 3D-Chiral quadratic indices of the “molecular pseudograph’s atom adjacency matrix”and their application to central chirality codification: classification of ACE inhibitors and prediction of r-receptor antagonist activities[J]. Bioorg Med Chem, 2004, 12( 20) : 5331-5342.
[6] Zhang Q Y,Aires-de-Sousa J. Structure-based classification of chemical reactions without assignment of reaction centers[J]. J Chem Inf Mode,2005, 45( 6) : 1775-1783.
[7] 冯长君,沐来龙,杨伟华,等. 用拓扑指数和神经网络研究有机污染物的生物富集因子[J]. 化学学报, 2008, 66( 19) : 2093-2098.
[8] 冯长君,杨伟华,沐来龙. 硝基芳烃对呆鲦鱼急性毒性的CoMFA 研究[J]. 南京理工大学学报, 2008, 32( 1) : 642-645.
[9] 冯长君,堵锡华,沐来龙. 用新型连接性指数与神经网络预测取代苯酚和取代苯甲酸生物降解性[J].南京理工大学学报, 2009, 33( 5) : 700-706.
[10] 刘东,章文军,许禄. 手性羟酸和氨基酸类化合物的构效关系研究[J]. 化学学报, 2009, 67( 2) : 145-150.
[11] 刘东,章文军,许禄. 一种新的拓扑指数用于手性化合物的构效关系研究[J]. 分析化学,2009,37( 4) : 543-547.
[12] Kier L B,Hall L H. Molecular connectivity in structureactivity analysis[M]. New York: John Wiley, 1986: 82.
[13] 冯长君. 价电子密度连接性指数及其应用[J]. 南京理工大学学报, 2000, 24( 3) : 223-227.
[14] 冯长君. 价电子能级连接性指数及其应用[J]. 无机化学学报, 1999, 15( 3) : 363-370.
[15] 徐寿昌. 有机化学[M]. 北京: 高等教育出版社, 1993: 45.
[16] Urra L S,Gonza’lez M P,Teijeira M. 2D-autocorrelation descriptors for predicting cytotoxicity of naphthoquinone ester derivatives against oral human epidermoid carcinoma[J]. Bioorganic and Medicinal Chemistry, 2007, 15( 10) : 3565-3571.
[17] Urra L S,Gonza’lez M P,Teijeira M. QSAR studies about cytotoxicity of benzophenazines with dual inhibition toward both topoisomerases I and Ⅱ: 3DMoRSE descriptors and statistical considerations about variable selection[J]. Bioorganic and Medicinal Chemistry, 2006, 14( 21) : 7347-7358.
[18] 冯长君. 3-取代硫基-5-( 2-羟基苯基) -4H-1,2 ,4 -三唑类化合物抑菌活性的定量构效关系和结构修饰的理论研究[J]. 化学学报, 2012, 70( 4) : 512-518.
[19] 冯长君,李鸣建,刘长宁. 用手性电性距离矢量研究手性有机酸保留指数[J]. 华中科技大学学报( 自然科学版) , 2009, 37( 11) : 124-128.
[20] 冯长君. 手性有机酸保留指数的手性指数及原子类型电拓扑指数模型[J]. 物理化学学报, 2010, 26( 1) : 193-198. 363

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Last Update: 2012-10-12