Crystal structure, Hirshfeld surface analysis, DFT and molecular docking investigation of 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 2-[2-(2-oxo-1,3-oxazolidin-3-yl)ethoxy]quinoline-4-carboxylate

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Bouzian Y., Baydere C., DEGE N., Ahabchane N. H., Mague J. T., Abudunia A., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.77, pp.28-39, 2021 (ESCI)

• Publication Type: Article / Article
• Volume: 77
• Publication Date: 2021
• Doi Number: 10.1107/s2056989020015960
• Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
• Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
• Page Numbers: pp.28-39
• Keywords: crystal structure, Covid-19, DFT, Hirshfeld surface analysis, oxazolidine, quinoline, Molecular docking, QUINOLINE
• Ondokuz Mayıs University Affiliated: Yes

Abstract

In the molecular structure of the title compound, C20H21N3O7, the quinoline ring system is slightly bent, with a dihedral angle between the phenyl and the pyridine rings of 3.47 (7)degrees. In the crystal, corrugated layers of molecules extending along the ab plane are generated by C-H center dot center dot center dot O hydrogen bonds. The intermolecular interactions were quantified by Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are from H center dot center dot center dot H (42.3%), H center dot center dot center dot O/O center dot center dot center dot H (34.5%) and H center dot center dot center dot C/C center dot center dot center dot H (17.6%) contacts. Molecular orbital calculations providing electron-density plots of the HOMO and LUMO as well as molecular electrostatic potentials (MEP) were computed, both with the DFT/B3LYP/6-311 G++(d,p) basis set. A molecular docking study between the title molecule and the COVID-19 main protease (PDB ID: 6LU7) was performed, showing that it is a good agent because of its affinity and ability to adhere to the active sites of the protein.