A Quantitative Structure-activity Relationship（QSAR） model was developed to predict the hallucinogenic activity of phenylalkylamines by Artificial Neural Network（ANN） method.Each compound was represented by the ca...A Quantitative Structure-activity Relationship（QSAR） model was developed to predict the hallucinogenic activity of phenylalkylamines by Artificial Neural Network（ANN） method.Each compound was represented by the calculated structural descriptors involving constitutional,topological,geometrical,electrostatic and quantum-chemical features of compound.The ANN method produced a nonlinear and seven-descriptor QSAR model with a standard error S = 0.0128 and a correlation coefficient R = 0.9752.The electronic properties of 75 phenylalkylamines were calculated with Gaussian 03 program at the DFT/B3LYP/6-311＋G（d,p） level.The quantum chemical analyses were performed from two aspects of frontier molecular orbital and charge distribution.The results show that seven structural describers are crucial to the hallucinogenic activity of phenylalkylamines and that the para-and ortho-positions could be active sites acting as electron donors.展开更多
DFT/B3LYP/6-311G＋（d,p） basis set including solvent effect was first used to calculate a set of molecular descriptors of 55 phenylalkylamine and 20 tryptamine compounds with hallucinogenic activity. Four quantitativ...DFT/B3LYP/6-311G＋（d,p） basis set including solvent effect was first used to calculate a set of molecular descriptors of 55 phenylalkylamine and 20 tryptamine compounds with hallucinogenic activity. Four quantitative structure-activity relationship （QSAR） models of the hallucinogenic activity for phenylalkylamines and tryptamines were obtained by employing multiple linear regression （MLR） method. The QSAR analysis indicated that electron-related descriptors were major contributors to the hallucinogenic activities of phenylalkylamines and tryp- tamines. In addition, electron-unrelated descriptors have some impact on the hallucinogenic activities of phenylal- kylamines. Based on the results of QSAR study, a novel Conformation Complementary Judgement, Transformation and Induction （CCJTI） model had been proposed to explain different action mechanisms of phenylalkylamines and tryptamines with their target receptors. It was concluded that phenylalkylamines might combine with receptor by electronic effect, but steric factor could affect it also, whereas tryptamines could act only through the electronic effect.展开更多
基金supported by the Natural Science Foundation of Shanxi Province (2007011025)
文摘A Quantitative Structure-activity Relationship（QSAR） model was developed to predict the hallucinogenic activity of phenylalkylamines by Artificial Neural Network（ANN） method.Each compound was represented by the calculated structural descriptors involving constitutional,topological,geometrical,electrostatic and quantum-chemical features of compound.The ANN method produced a nonlinear and seven-descriptor QSAR model with a standard error S = 0.0128 and a correlation coefficient R = 0.9752.The electronic properties of 75 phenylalkylamines were calculated with Gaussian 03 program at the DFT/B3LYP/6-311＋G（d,p） level.The quantum chemical analyses were performed from two aspects of frontier molecular orbital and charge distribution.The results show that seven structural describers are crucial to the hallucinogenic activity of phenylalkylamines and that the para-and ortho-positions could be active sites acting as electron donors.
基金Project supported by the Natural Science Foundation of Shanxi Province （No. 2007011025） and Scientific Research Foundation for the Returned Overseas Chinese Scholars of Shanxi Province.
文摘DFT/B3LYP/6-311G＋（d,p） basis set including solvent effect was first used to calculate a set of molecular descriptors of 55 phenylalkylamine and 20 tryptamine compounds with hallucinogenic activity. Four quantitative structure-activity relationship （QSAR） models of the hallucinogenic activity for phenylalkylamines and tryptamines were obtained by employing multiple linear regression （MLR） method. The QSAR analysis indicated that electron-related descriptors were major contributors to the hallucinogenic activities of phenylalkylamines and tryp- tamines. In addition, electron-unrelated descriptors have some impact on the hallucinogenic activities of phenylal- kylamines. Based on the results of QSAR study, a novel Conformation Complementary Judgement, Transformation and Induction （CCJTI） model had been proposed to explain different action mechanisms of phenylalkylamines and tryptamines with their target receptors. It was concluded that phenylalkylamines might combine with receptor by electronic effect, but steric factor could affect it also, whereas tryptamines could act only through the electronic effect.
