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QSPR/QSAR studies of 2-furylethylenes using bond-level quadratic indices and comparison with other computational approaches

Abstract:

The recently introduced, non-stochastic and stochastic quadratic indices (Marrero-Ponce et al. J. Comp. Aided Mol. Des. 2006, 20, 685-701) were applied to QSAR/QSPR studies of heteroatomic molecules. These novel bond-based molecular descriptors (MDs) were used for the pbkp_rediction of the partition coefficient (log P), and the antibacterial activity of 34 derivatives of 2-furylethylenes. Two statistically significant QSPR models using non-stochastic and stochastic bond-based quadratic indices were obtained (R2 = 0.971, s = 0.137 and R2 = 0.986, s = 0.096). These models showed good stability to data variation in leave-one-out (LOO) cross-validation experiment (q2 = 0.9975, sCV = 0.164 and q2 = 0.947, sCV = 0.114). The best two discriminant models computed using the non-stochastic and stochastic molecular descriptors had globally good classification of 94.12% in the training set. The external pbkp_rediction sets had accuracies of 100% in both cases. The comparison with other approaches (edge- and vertexbased connectivity indices, total and local spectral moments, quantum chemical descriptors as well as with other TOMOCOMD-CARDD MDs) revealed the good performance of our method in this QSPR study. The obtained results suggest that it is possible to obtain a good estimation of physical, chemical and physicochemical properties for organic compounds with the present approach. © 2013, Sociedad Química de México.