Hydrazineylidene‐3‐oxopropanal derivatives as antiviral agents for treatment of HBV and HCV: Experimental, DFT, and molecular docking studies

Abstract

In this study, two derivatives of hydrazineylidene‐3‐oxopropanal: chlorophenyl (CPHO) and Nitrophenyl (NPHO) substituted hydrazineylidene compounds were synthesized, spectroscopically characterized using (FT‐IR, UV, and NMR), and theoretically modelled as a potential drug for the treatment of antiviral hepatitis (HBV and HCV) using in‐sillico molecular docking approach. Electronic structure investigation based on density functional theory (DFT) at the B3LYP/6‐311++G(d,p) level of theory was conducted for the investigation of the structural, reactivities, and electronic properties of the studied compounds. The FT‐IR analysis in gas, water, ethanol and DMSO indicates a maximum stretching vibrations frequencies of C‐H in NPHO between 3249.38 to 3254.77 cm‐1 and 3236.04 to 3240.66 cm‐1 for CPHO, N‐H for NPHO is 3309.81 to 3336.37 cm‐1, and CPHO is 3330.11 to 3331.18 cm‐1, C=O in NPHO to be 1685.55 to 1705.60 cm‐1, and 1700.31 to 1679.15 cm‐1 for CPHO. The C‐N stretching vibrations in NPHO were 1519.98 to 1562.06 cm‐1 and 1430.05 to 1460.33 cm‐1 for CPHO. The UV‐Vis analysis indicates that NPHO wavelength absorption spectrum showed high excitation energy bands between 369.74 to 440.60 nm and CPHO at 178.95 to 434.08 nm. The highest stabilization energy of NPHO is LP (1) N12 donor and LP*(1) H10 acceptor with a value of 417.54 kcal/mol compared to πC17 ‐ O18 donor and π*C19 ‐ C28 acceptor with a value of 108.33 kcal/mol for CPHO. The molecular binding affinity of CPHO and NPHO had a high mean binding affinity of ‐5.83 and ‐6.05 kcal/mol, compared to the standard antiviral drugs with ‐5.00 kcal/mol. Therefore, the compounds show excellent reactivity based on the electronic structure, spectroscopic characterization and represent a potential antiviral agent treatment for HBV and HCV.