In Vitro Evaluation, Molecular Docking, and Lipinski’s Rule Analysis of a new Triazinone-Based Schiff Base for Potential Pharmacological Applications

(E)-6-methyl-4-((4-methylbenzylidene)amino)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (1), was synthesized from the reaction of 4-amino-3-mercapto-6-methyl-5-oxo-1,2,4-triazine (AMTTO) and 4-methyl benzaldehyde under microwave conditions and characterized through ¹H-NMR, FTIR spectroscopy, and single-crystal X-ray diffraction. The Hirshfeld surface was analyzed and results indicate a significant effect of hydrogen interactions and their role in the stability of the crystal lattice of the 1. The in vitro antibacterial activities were evaluated using the disk diffusion technique. 1 displays moderate to significant effect on bacterial strains. In silico Molecular docking simulations were performed to investigate the interaction 1 with the active site of three target proteins. Discovery Studio Visualizer and LigPlot+ software was used to illustrate molecular docking results. The best confirmation from molecular docking studies shows that the free energies of binding for the studied ligands were -6.7, -6.6, and -6.6 kcal/mol, as were the creation of hydrogen bonds between the studied compound and the target proteins. In silico prediction of physicochemical properties (Lipinski's rule of five) and bioavailability radar were determined by the SwissADME database. The physicochemical property analysis revealed that 1 has a bioavailability score of 0.55. The results of this study indicate that 1 could be a lead compound for developing antimicrobial and antiviral compounds.