Synthesis, Crystal Structure, Hirshfeld Surface Analysis, NCI-RDG, Molecular Docking, Molecular Dynamic Simulations, and Toxicity Assessment of 2-((2,4-Dimethoxybenzylidene) Hydrazono)-1,2-Diphenylethanone

Abstract

This study reports the synthesis of a hydrazone-like compound with the chemical formula C23H20N2O3. The synthesis involved reacting benzilmonohydrazone with 2,4-dimethoxybenzaldehyde at 85 degrees C for 3 hours. The mixture was cooled, filtered, and washed with ethanol. The resultant solid was then recrystallized in a suitable solvent to isolate the desired product. To investigate the molecular geometrical properties of the 2-(2, 4-dimethoxybenzylidene) hydrazone)-1, 2-diphenylethanone (DBHDE) molecule, both theoretical and experimental methods were employed. Density functional theory (DFT) calculations using the B3LYP functional and a 6-311G (d, p) basis set were performed, and the calculated geometric parameters showed good agreement with the experimental data. In addition, Hirshfeld surface analysis and 2D fingerprint plots indicated that the most significant intermolecular interactions in the crystal packing of DBHDE are H...H (48.8%) and C...H/H...C (28.4%). According to NCI-RDG analysis, the centers of the three benzene rings represent the highest repulsive interaction regions in the molecule. Finally, the biological potential of the synthesized compound was thoroughly evaluated using molecular docking studies, molecular dynamics simulations, in silico ADME-T investigation, and biochemical analyses (cholesterol, creatinine and transaminases) in wistar rats.