Structural Characterization, and Computational Analysis of (E)-6-bromo-3-(3,4-dimethoxybenzylidene)-7-methoxy-1-tosyl-2,3-dihydroquinolin-4(1H)-one

The target compound (E)-6-bromo-3-(3,4-dimethoxybenzylidene)-7-methoxy-1-tosyl-2,3-dihydroquinolin-4(1H)-one, which is a quinolone derivative holding tosyl group has been successfully synthesized through reported method via aza Baylis Hillman, 1,3-rearrangement and intramolecular amination reactions. The structure of the newly synthesized compound was characterized by, FTIR, NMR, HRMS, and X-ray diffraction techniques. The compound crystallizes in, a monoclinic crystal system with a space group of P2(1)/n and was determined with a final residual value (R) equal to 0.0332. A molecular docking study revealed feasible binding modes of the title compound to the protein target, which showed small binding free energies. The inter-molecular interaction of the target molecule was studied by utilizing 2D and 3D Hirshfeld surface techniques. The optimized molecular geometry, vibrational frequencies, and frontier molecular orbital energies of the compound were studied using density functional theory. The UV-visible study was also carried out to understand electron interaction.

Automated summary

The target compound, a quinolone derivative with a tosyl group, was successfully synthesized using reported methods involving aza Baylis Hillman, 1,3-rearrangement, and intramolecular amination reactions. The structure of the compound was characterized using FTIR, NMR, HRMS, and X-ray diffraction techniques. Molecular docking study revealed the binding modes and small binding free energies of the compound to the protein target.