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

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Abstract

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 P21/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.

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Authors and Affiliations

  1. Department of Physics, Mysore University School of Engineering, Manasagangotri, University of Mysore, 570006, Karnataka, Mysore, India

    D. Sahana

  2. Department of Physics, Vidyavardhaka College of Engineering, Visvesvaraya Technological University, 570002, Karnataka, Mysore, India

    C. S. Dileep

  3. Department of Chemistry, Vidyavardhaka College of Engineering, Visvesvaraya Technological University, 570002, Karnataka, Mysore, India

    N. Srikantamurthy & B. Vrushabendra

  4. Department of Physics, The National Institute of Engineering (NIE), 570008, Karnataka, Mysore, India

    Chandra

  5. Department of Physics, R V College of Engineering, 560059, Karnataka, Bengaluru, India

    B. M. Rajesh

  6. Department of Studies in Organic Chemistry, University of Mysore, 570006, Karnataka, Mysuru, India

    D. M. Gurudatt

  7. Department of Physics, NIE First Grade College, 570008, Karnataka, Mysore, India

    R. Gopalkrishne Urs

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  1. D. Sahana
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  4. B. Vrushabendra
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  8. R. Gopalkrishne Urs
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Corresponding authors

Correspondence to C. S. Dileep or R. Gopalkrishne Urs.

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The data were deposited in the Cambridge Crystallographic Database Deposition Number for molecule (3) is 2205295, contains the supplementary crystallographic data for these compounds, and can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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Sahana, D., Dileep, C.S., Srikantamurthy, N. et al. Structural Characterization, and Computational Analysis of (E)-6-bromo-3-(3,4-dimethoxybenzylidene)-7-methoxy-1-tosyl-2,3-dihydroquinolin-4(1H)-one. Crystallogr. Rep. 68, 14–23 (2023). https://doi.org/10.1134/S1063774523330015

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  • DOI: https://doi.org/10.1134/S1063774523330015

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