Journal of Chemical and Pharmaceutical Research (ISSN : 0975-7384)

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Original Articles: 2010 Vol: 2 Issue: 6

DFT-Based QSAR Prediction of 1-Octanol/Water Partition Coefficient of Adamantine derivatives drugs


A quantitative structure property relationship (QSP R) study was performed to develop a model that relates the structures of 39 ofAdamantine derivativ es drugs to simple descriptors. The usefulness of t he quantum chemical descriptors, were calculated at th e level of the DFT theory using 6-31+G** basis set , and used to represent molecular structures. A subse t of the calculated descriptors selected using step wise regression that used in the QSPR model development. In this study Multiple Linear Regressions (MLR) were employed to model the relationships between mo lecular descriptors and biological activities of molecules using stepwise method and genetic algorit hm as variable selection tools.. Biological activit ies contain the octanol/water partition coefficient (lo g P). The final regression equation included four parameters that consisted of Clog P, Mulliken charg e, Isotropic parameters and Mass, all of which coul d be related to log P. Application of the developed m odel to a testing set of 39 of Adamantine derivativ es drugs demonstrates that the new model is reliable w ith good predictive accuracy and simple formulation . The use of descriptors calculated only from molecul ar structure eliminates the need for experimental determination of properties for use in the correlat ion and allows for the estimation of log P for mole cules not yet synthesized. The prediction results are in good agreement with the experimental values. Statis tical qualities (R MAX = 0.927 , R 2 MAX = 0.858 Q 2 =0.713at B3LYP/6-31+G**) was obtained by this appro ach.