Analeptic activity of 2-Hydroxyl-5-Nitrobenzaldehyde: Experimental, DFT studies, and in silico molecular docking approach

This study was carried out to evaluate the spectroscopic, molecular properties, and in silico biological assessment of 2-Hydroxyl-5-Nitrobenzaldehyde (NSA) characterized by FT-IR, UV, NMR spectral, and first-principle density functional theory (DFT). The optimized molecular geometry, the vibrational wavenumbers, and infrared intensities activities were calculated by using the density functional theory (DFT) B3LYP method with a 6–311++G(d,p) basis set. The detailed interpretation of the vibrational spectra was assigned by VEDA program. The results of NBO analysis show that LP(3)O12 and LP(2)O13 bonding orbitals participated as donors and the π*N10–O11 and π*C2–C3 antibonding orbitals as acceptors in all the four phases understudy with occupancies in the range of 1.45453, 1.85287 leading to the stabilization energy of 160.60 and, 30.55 kcal/mol, which results in intramolecular charge transfer leading to the stabilization of the molecule. Moreover, Drug likeness properties of NSA are predicted. The predicted ADMET properties showed high gastrointestinal absorption, does not permeant the brain–blood barrier, nor any Cytochrome P450 inhibition (1A2, 2C19, 2C9, 2DA, 3A4, and 3A4) without violating any of the Lipinski rules. The result from the molecular docking showed that NSA has the highest negative mean binding affinity of −5.71 kcal/mol, followed by CFN and EDE which are approximately equal at −5.176 and −5.004 kcal/mol respectively and added to a more significant hydrogen bond with amino acids residues of the selected receptor proteins. Therefore, it could be said that NSA is a potential analeptic agent. [Display omitted] •Spectroscopic studies of 2-Hydroxyl-5-Nitrobenzaldehyde (NSA) by FT-IR, FT-Raman, 1H-NMR techniques was done.•Vibrational assignments in different solvents depicted changes in functional group vibrations.•Electronic excitations in different solvents showed possible solvatochromic effects.•From NBO analysis, LP(3)O12 and LP(2)O13 orbitals were donors while π*N10–O11 and π*C2–C3 orbitals were acceptors.•The results from molecular docking proved that NSA is a potential Analeptic agent.