TOPOCHEMICAL MODELS FOR THE PREDICTION OF LIPOPHILICITY OF 1,3-DISUBSTITUTED PROPAN-2-ONE ANALOGS
Harish Dureja, Vipin Kumar, Sunil V. Gupta, Anil Kumar Madan · Journal of Theoretical and Computational Chemistry · 2007
In the present study, the relationship between the topochemical indices and log P values of 1,3-disubstituted propan-2-one analogs has been investigated. Three topochemical indices, Wiener's topochemical index — a distance-based topochemical descriptor, molecular connectivity topochemical index — an adjacency-based topochemical descriptor, and eccentric connectivity topochemical index — an adjacency-cum-distance-based topochemical descriptor, were used for the present investigation. The values of the Wiener's topochemical index, molecular connectivity topochemical index, and eccentric connectivity topochemical index were computed for each of the 45 analogs constituting the data set using an in-house computer program. The predicted log P values using leave-one-out (LOO) procedure exhibited a q2 of 0.72, 0.70, and 0.71 with reported log P values for Wiener's topochemical index, molecular connectivity topochemical index, and eccentric connectivity topochemical index, respectively. Separate models were developed using training set and log P of each analog in the independent test set was predicted using these models. The correlation of predicted log P values with the reported values, for independent test set, were in good agreement with those predicted using LOO procedure.