Abstract

MARTINEZ ALBELO, Eugenio R. et al. QSPR/QSAR Studies of 2-Furylethylenes Using Bond-Level Quadratic Indices and Comparison with Other Computational Approaches. J. Mex. Chem. Soc [online]. 2013, vol.57, n.1, pp.61-68. ISSN 1870-249X.

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 prediction 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, s_CV = 0.164 and q² = 0.947, s_CV = 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 prediction sets had accuracies of 100% in both cases. The comparison with other approaches (edge- and vertex-based 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.

Keywords : TOMOCOMD-CARDD Software; non-Stochastic and Stochastic Bond-Based Quadratic Indices; Edge-Adjacency Matrix; Stochastic Matrix; QSPR/QSAR Model; 2-furylethylene.

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