Crystal structure, Hirshfeld surface analysis, DFT and mol-ecular docking investigation of 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 2-[2-(2-oxo-1,3-oxazolidin-3-yl)eth-oxy]quinoline-4-carboxyl-ate.

El Mokhtar Essassi,Joel T. Mague,Noureddine Hamou Ahabchane,Cemile Baydere,Abdulmalik Abudunia,Necmi Dege,Younos Bouzian,Khalid Karrouchi

doi:10.1107/s2056989020015960

El Mokhtar Essassi, Joel T. Mague + Show 6 more

Open Access

https://doi.org/10.1107/s2056989020015960

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Abstract

In the mol-ecular 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)°. In the crystal, corrugated layers of mol-ecules extending along the ab plane are generated by C-H⋯O hydrogen bonds. The inter-molecular inter-actions were qu-anti-fied by Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are from H⋯H (42.3%), H⋯O/O⋯H (34.5%) and H⋯C/ C⋯H (17.6%) contacts. Mol-ecular orbital calculations providing electron-density plots of the HOMO and LUMO as well as mol-ecular electrostatic potentials (MEP) were computed, both with the DFT/B3LYP/6-311 G++(d,p) basis set. A mol-ecular docking study between the title mol-ecule 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.

Highlights

Younos Bouzian,a Cemile Baydere,b* Necmi Dege,b Noureddine Hamou Ahabchane,a Joel T
The most significant contributions to the crystal packing are from HÁ Á ÁH (42.3%), HÁ Á ÁO/OÁ Á ÁH (34.5%) and HÁ Á ÁC/ CÁ Á ÁH (17.6%) contacts
In a continuation of our research work devoted to the syntheses and crystal structures of quinoline derivatives (Bouzian et al, 2019a), we report the molecular and crystal structures, Hirshfeld surface analysis, density functional theory (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

Summary

Chemical context

Quinoline and its derivatives have attracted the interest of synthetic and biological chemists because of their interesting chemical and pharmacological properties (Chu et al, 2019), including antibacterial (Bouzian et al, 2020), anticancer (Tang et al, 2018), antitubercular (Xu et al, 2017), anti-COVID19 (Gao et al, 2020), antimalarial (Hu et al, 2017), antileishmanial (Palit et al, 2009) and anti-inflammatory (Pinz et al, 2016) activities. Many studies have shown that quinoline derivatives are good corrosion inhibitors (Douche et al 2020). In a continuation of our research work devoted to the syntheses and crystal structures of quinoline derivatives (Bouzian et al, 2019a), we report the molecular and crystal structures, 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

Structural commentary

Database survey

Hirshfeld surface analysis

Frontier molecular orbital analyses

Molecular electrostatic potentials

Molecular docking study

Synthesis and crystallization

Findings

33 Bouzian et al C20H21N3O7 supporting information supporting information