Synthesis, spectroscopic characterizations, DFT, molecular docking and molecular dynamics simulations of a novel 2-methyl-3H-benzimidazolo[1,2-b][1,2,4]triazepin-4(5H)-one

Abstract

A novel compound named 2-methyl-3 H -benzimidazolo[1,2-b][1,2,4]triazepin-4(5 H )-one (C 11 H 10 N 4 O) has been synthesized and characterized by spectroscopic techniques (FT-IR),UV–Vis, 1 H NMR, 13 C NMR and mass spectra. The optimized molecular structure analyses, vibrational wave numbers, 13 C and 1 H NMR chemical shifts of the title molecule have been performed at DFT/B3LYP method with 6-31 + G(d,p) basis set. The electronic absorption wavelengths computed using B3LYP, B3P86 and PBE0 hybrid functional. The scaled vibrational modes, and the predicted 13 C NMR and 1 H NMR chemical shifts are relatively in good agreement with the corresponding experimental ones. However, B3LYP, B3P86 and PBE0 hybrid functional fail in reproduction of experimental λ MAX of the tilted compound and it is underestimated by the tested hybrid functionals with deviations to the experimental values of 30, 34 and 40 nm for B3LYP, B3P86 and PBE0, respectively. In addition, molecular docking and molecular dynamics simulations of titled compound were carried out to determine its binding modes and stability within the leucine-rich repeat kinase 2 active site. • 2-Methyl-3 H -benzimidazolo[1,2- b ] [1,2,4]triazepin-4(5 H )-one was synthesized and characterized. • Molecular structure is characterized by using spectroscopic techniques. • DFT calculations at B3LYP allow a better reproduction of the experimental data. • Molecular docking and molecular dynamics analysis were carried with leucine-rich repeat kinase 2 complex.