Theoretical Scales of Hydrogen Bond Acidity and Basicity for Application in QSAR/QSPR Studies and Drug Design. Partitioning of Aliphatic Compounds
Theoretical Scales of Hydrogen Bond Acidity and Basicity for Application in QSAR/QSPR Studies and Drug Design. Partitioning of Aliphatic Compounds
复制标题
氢键酸度和碱度的理论尺度在 QSAR/QSPR 研究和药物设计中的应用。
DOI：
10.1021/ci0342932
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发表时间：
2004
期刊：
影响因子：
--
通讯作者：
A. Katritzky
中科院分区：
文献类型：
--
作者：
A. Oliferenko;Polina V. Oliferenko;J. Huddleston;R. Rogers;V. Palyulin;N. Zefirov;A. Katritzky
现有的氢键（HB）的供体和受体规模和明显的物理考虑的唯象分析，使建立新的定量尺度的氢键的碱性和酸性。利用分子图和Hinze和Jaffe的轨道电负性表示的化学结构作为输入数据。所得标度与几种实验溶剂极性标度（如和、pK（HB）和E（T））相关性良好（30）。为了证明新的数量的适用性，我们已经将它们应用到七个平衡分配数据集：辛醇-水，十六烷-水，氯仿-水，气体-水，气体-辛醇，气体-十六烷，气体-氯仿分配系数。氢键描述符补充时，由一个腔形成的长期和偶极长期表现出高性能的脂肪族化合物的分配系数的相关性。这些新的HB描述符可用于研究氢键和流体相平衡，以及配体对接和描述符ADME评价的评分功能。
Phenomenological analysis of existing hydrogen bond (HB) donor and acceptor scales and apparent physical considerations have enabled the establishment of new quantitative scales of hydrogen bond basicity and acidity. Chemical structures represented by molecular graphs and the orbital electronegativities of Hinze and Jaffe are utilized as an input data. The scales obtained correlate well with several experimental solvent polarity scales such as and, pK(HB), and E(T)(30). To demonstrate the applicability of the new quantities, we have applied them to seven equilibrium partitioning data sets: octanol-water, hexadecane-water, chloroform-water, gas-water, gas-octanol, gas-hexadecane, and gas-chloroform partition coefficients. The hydrogen bond descriptors when supplemented by a cavity-forming term and a dipolarity term show high performance in correlations of the partition coefficients of aliphatic compounds. These new HB descriptors can be used in studying hydrogen bonding and fluid phase equilibria as well as scoring functions in ligand docking and descriptors in ADME evaluations.