Insights into β-Diketone: A Multi-Faceted Study from Crystal Structure to Molecular Docking and Antioxidant Potential

A β-diketone (1,3-benzoylcamphor) compound, derived from (1R)-(+)-camphor and methyl-benzoate, was synthesized under mild conditions and characterized by spectroscopic and single-crystal X-ray diffraction technics. The main conformational difference between the molecules is in the orientation of the plane of the benzyl rings with respect to the camphor fragment. The molecule crystallizes in the orthorhombic P2₁2₁2₁ space group with one molecule in the asymmetric unit. The β-diketone molecules are interconnected to one another by C–H···π and O–H···C bonding. The Hirshfeld surface analysis reveals that the primary contributors to crystal packing are H–H interactions (67.2%), followed by H–C (17.5%) and H–O (15.3%) interactions. Also, we investigated the structure, vibrational properties, and electronic transitions of the ligand through DFT and TD-DFT methods. The findings indicate a strong correlation between the geometric parameters and the simulated UV/Vis absorption spectrum with experimental results. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay was used to assessed the antioxidant activity of the β-diketone. The molecular docking modelling is used to examine the interactions between the β-diketone and the major proteases of the SARS-CoV-2 virus (PDB ID: 6LU7). When compared to the recommended medication, chloroquine, the β-diketone showed a greater estimated free binding energy. These findings have the potential to facilitate the development and testing as new therapies for SARS-CoV-2, thereby enhancing the ability to combat the virus more effectively.