QSAR Modeling Using Quantum Chemical Descriptors of Benzimidazole Analogues With Antiparasitic Properties

Abstract

This article describes how benzimidazole is a privileged scaffold that has been used as a basis to develop antiparasitic compounds. Herein, the relationship between the chemical structure and biological activity against Trichomonas vaginalis of sixty nine benzimidazole analogues was studied using Density Functional Theory and multiple linear regression analysis. The best QSAR model obtained highlights the correlation between the pIC50 with frontier orbital energy gap, Van der Waals volume, number of hydrophobic atoms, Harmonic Oscillator Model of Aromaticity Index, partition coefficient, and number of total second C(sp3). The model has values of R2 = 0.784, Q2 = 0.720 with the validation parameters: F-test = 37.51, SPRESS = 0.274, and SDEP = 0.262. The average values of R2adj (Obs) and (Calc) are very close (0.763 and 0.760 respectively), which suggests a relatively stable predictively of the model for these data. The QSAR model developed can be employed to estimate the biological activity of new compounds based on a benzimidazole core scaffold.