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

• Published in: Crystallography reports 2023-02, Vol.68 (1), p.14-23
• Main Authors: Sahana, D., Dileep, C. S., Srikantamurthy, N., Vrushabendra, B., Chandra, Rajesh, B. M., Gurudatt, D. M., Urs, R. Gopalkrishne
• Format: Article
• Language: English
• Subjects: Binding; Crystallographic Symmetry; Crystallography and Scattering Methods; Density functional theory; Molecular docking; Molecular interactions; Molecular orbitals; NMR; Nuclear magnetic resonance; Physics; Physics and Astronomy; Structural analysis; Vibrational spectra
• ISSN: 1063-7745; 1562-689X
• DOI: 10.1134/S1063774523330015

The target compound ( E )-6-bromo-3-(3,4-dimethoxybenzylidene)-7-methoxy-1-tosyl-2,3-dihydroquinolin-4(1 H )-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 P 2 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.