Bond-based global and local (bond, group and bond-type) quadratic indices and their applications to computer-aided molecular design. 1. QSPR studies of diverse sets of organic chemicals.
The concept of atom-based quadratic indices is extended to a series of molecular descriptors (MDs) (both total and local) based on adjacency between edges. The kth edge-adjacency matrix (E ( k )) denotes the matrix of bond-based quadratic indices (non-stochastic) with respect to the canonical basis set. The kth "stochastic" edge-adjacency matrix, ES ( k ), is here proposed as a new molecular representation easily calculated from E ( k ). Then, the kth stochastic bond-based quadratic indices are calculated using ES ( k ) as operators of quadratic transformations. The study of six representative physicochemical properties of octane isomers was used to compare the ability of both series of MDs to produce significant quantitative structure-property relationship (QSPR) models. Moreover, the general performance of the new MDs in this QSPR study has been evaluated with respect to other 2D/3D well-known sets of indices and the obtained results shown a quite satisfactory behavior of the present method. The novel bond-level MDs were also used for the description and prediction of the boiling point of 28 alkyl-alcohols and to the modeling of the specific rate constant (log k) of 34 derivatives of 2-furylethylenes. These models were statistically significant and showed very good stability to data variation in leave-one-out (LOO) cross-validation experiment. The comparison with other approaches (edge- and vertices-based connectivity indices, total and local spectral moments, and quantum chemical descriptors as well as E-state/biomolecular encounter parameters) expose a good behavior of our method in this QSPR studies. The approach described in this report appears to be a very promising structural invariant, useful for QSPR/QSAR studies, similarity/diversity analysis, and computer-aided "rational" molecular (drug) design.
Marrero-Ponce
Yovani
Y
Unit of Computer-Aided Molecular 'Biosilico' Discovery and Bioinformatic Research (CAMD-BIR Unit), Faculty of Chemistry-Pharmacy, Central University of Las Villas, Santa Clara, Villa Clara, 54830, Cuba. ymarrero77@yahoo.es
Torrens
Francisco
F
Alvarado
Ysaias J
YJ
Rotondo
Richard
R
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003198:Computer Simulation; D017076:Computer-Aided Design; D015195:Drug Design; D008956:Models, Chemical; D009930:Organic Chemicals / Q000737:chemistry* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D013269:Stochastic Processes
D009930:Organic Chemicals