Synthesis, biological evaluation and molecular modeling investigation of some new benzimidazole analogs as antiviral agents

ABSTRACT

A set of heterocyclic benzimidazole derivatives bearing 1,3,5-triazine group with different substituents at C-2 and C-5 of the benzimidazole ring have been synthesized and evaluated for their antiviral activities against HSV-1. The structures of these compounds have been established by analytical data, IR spectra, [1]H NMR, and mass spectra. Compounds 8a and 8b proved to be the most active antiherpetic agents in this study, at EC[50]% concentrations of 2.9, 3.4 mg/ml, respectively. Computational evaluation of the quantum chemical descriptors such as hydrophobicity [log P], HOMO and LUMO, and the gap energy, were calculated and correlated with the antiviral activity. The tested compounds showed proper degree of hydrophobicity [<0.5 - >5]. The HOMO-LUMO gap energy values of the tested compounds are comparable with the observed values for the antiviral drug, Acyclovir