Ethyl 2-{[2-(2-ethoxy-2-oxoethoxy)quinolin-4-yl]carbonyloxy}acetate

Bouzian, Younos; Hlimi, Fouzia; Sebbar, Nada Kheira; Hafi, Mohamed El; Hni, Brahim; Essassi, El Mokhtar; Mague, Joel T.

doi:10.1107/s2414314618014384

Cited by 5 publications

(6 citation statements)

References 8 publications

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“…A non-alkylated analogue, namely quinoline and its derivatives, has been reported (Filali Baba et al, 2016Baba et al, , 2017, as well as three similar structures, see: Bouzian et al, 2018Bouzian et al, , 2019aFilali Baba et al, 2019.…”

Section: Database Surveymentioning

confidence: 95%

“…They are also used as inhibitors of gastric (H + /K + )-ATPase (Ife et al, 1992), dihydroorotate dehydrogenase (Chen et al, 1990) and 5-lipoxygenase (Musser et al, 1987). As a continuation of our research on the development of N-substituted quinoline derivatives and the assessments of their potential pharmacological activities (Filali Baba et al, 2016Bouzian et al, 2018Bouzian et al, , 2019a, we have studied the condensation reaction of propargyl bromide with 2-chloroethyl 2-oxo-1,2-dihydroquinoline-4-carboxylate under phase-transfer catalysis conditions using tetra-n-butylammonium bromide (TBAB) as catalyst and potassium carbonate as base. We report herein on the synthesis and the molecular and crystal structures of the title compound along with the Hirshfeld surface analysis and the intermolecular interaction energies and the density functional theory (DFT) computational calculation carried out at the B3LYP/6-311 G(d,p) level.…”

Section: Chemical Contextmentioning

confidence: 99%

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Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-chloroethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

Hayani¹,

Baba²,

Hökelek

et al. 2019

Acta Cryst E

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The title compound, C15H12ClNO3, consists of a 1,2-dihydroquinoline-4-carboxylate unit with 2-chloroethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the molecules form zigzag stacks along the a-axis direction through slightly offset π-stacking interactions between inversion-related quinoline moieties which are tied together by intermolecular C—HPrpnyl...OCarbx and C—HChlethy...OCarbx (Prpnyl = propynyl, Carbx = carboxylate and Chlethy = chloroethyl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (29.9%), H...O/O...H (21.4%), H...C/C... H (19.4%), H...Cl/Cl...H (16.3%) and C...C (8.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPrpnyl...OCarbx and C—HChlethy...OCarbx hydrogen bond energies are 67.1 and 61.7 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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Section: Database Surveymentioning

confidence: 95%

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-chloroethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

Hayani¹,

Baba²,

Hökelek

et al. 2019

Acta Cryst E

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“…They are also considered to be important scaffolds for the development of new molecules of pharmaceutical interest (Filali Baba et al, 2020;Bouzian et al, 2018).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis, interaction energy and DFT calculations and energy frameworks of methyl 6-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate

Baba¹,

Hayani²,

Dalbouha³

et al. 2022

Acta Cryst E

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In the title compound, C12H10ClNO3, the dihydroquinoline moiety is not planar with a dihedral angle between the two ring planes of 1.61 (6)°. An intramolecular C—H...O hydrogen bond helps to establish the rotational orientation of the carboxyl group. In the crystal, sheets of molecules parallel to (10\overline{1}) are generated by C—H...O and C—H...Cl hydrogen bonds, and are stacked through slipped π-stacking interactions between inversion-related dihydroquinoline units. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (34.2%), H...O/O...H (19.9%), H...Cl/Cl...H (12.8%), H...C/C...H (10.3%) and C...C (9.7%) interactions. Computational chemistry indicates that in the crystal, the C—H...Cl hydrogen-bond energy is −37.4 kJ mol−1, while the C—H...O hydrogen-bond energies are −45.4 and −29.2 kJ mol−1. An evaluation of the electrostatic, dispersion and total energy frameworks revealed that the stabilization is dominated via the dispersion energy contribution. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state, and the HOMO—LUMO behaviour was elucidated to determine the energy gap.

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“…Gauss view 5.0 interface program [35] was used to prepare input to Gaussian and to examine graphically the output that Gaussian calculates. The initial coordinates for the molecular optimization and other computations in compound 3 [36] and 4 were utilized from CIF (crystal information file) files.…”

Section: Computational Detailsmentioning

confidence: 99%

Synthesis, spectroscopic characterization, DFT, molecular docking and in vitro antibacterial potential of novel quinoline derivatives

Bouzian

Sert

Karrouchi

et al. 2021

Journal of Molecular Structure

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Ethyl 2-{[2-(2-ethoxy-2-oxoethoxy)quinolin-4-yl]carbonyloxy}acetate

Cited by 5 publications

References 8 publications

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-chloroethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-chloroethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

Crystal structure, Hirshfeld surface analysis, interaction energy and DFT calculations and energy frameworks of methyl 6-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate

Synthesis, spectroscopic characterization, DFT, molecular docking and in vitro antibacterial potential of novel quinoline derivatives

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