(E)-2-((3-Nitrophenyl)Diazenyl)-3-Oxo-3-Phenylpropanal: Experimental, DFT Studies, and Molecular Docking Investigations

In 2019 alone, the WHO declared about 325 million people worldwide to be infected with hepatitis, resulting to mortality of about 1.4 million annually. In this study the potential of (E)-2-((3-nitrophenyl)diazenyl)-3-oxo-3-phenylpropanal (NDPP) as a potential antiviral agent for hepatitis B (HBV) and C (HCV) viruses management was investigated through spectroscopic (UV, FT-IR, and NMR), density functional theory (DFT) at different functionals (B3LYP, M06-2X, and ωB97XD) and molecular docking approaches. HOMO–LUMO analysis and quantum descriptor indicates an Energy gap (∆Eg) of 3.720, 5.950 and 7.420 eV for B3LYP, M06-2X, and ωB97XD and other parameters indicates a good molecular reactivity. Comparing the vibrational analysis in gas and water medium showed the lowest RMSD of 10.656 with M06-2X, 11.725 for ωB97XD and which can be attributed to the effect hydrogen bond due to solvation with water. The stabilization energy from natural bond orbital (NBO) analysis indicated the highest for intra-charge transfer (ICT) from acceptor to donor of 394.36 kcal/mol (π*C₂₂–C₃₁ → π*C₁₆–C₁₇) for ωB97XD, M06-2X with 282.58 kcal/mol (π*C₂₈–C₂₉ → π*C₃-C₂₇), and 254.88 kcal/mol (π*C₂₉–C₃₀ → π*C₁–C₃) for B3LYP. The UV–Vis analysis for excitation due to π → π* transitions, λmax values increased from gas to water phase, B3LYP (376.96 nm, 408.87 nm), M06-2X (330.83 nm, 349.24 nm) and ωB97XD (322.52 nm, 332.41 nm) for gas and water phase. The molecular docking results, indicated a mean binding affinity of − 7.10 kcal/mol for the ligand versus Tenofovir as reference agent for HBV with − 5.93 kcal/mol, and − 7.8 kcal/mol against Sofosbuvir as reference agent for HCV with − 8.6 kcal/mol. The study concludes, that due to these excellent molecular electronic structure activities and molecular docking results observed, NDPP is a potential antiviral agent HBV and HCV management. Graphical abstract: [Figure not available: see fulltext.]