Structure-activity Relationship Model for Predicting the Hallucinogenic Activity of Phenylalkylamines

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.