Crystal structure and DFT study of benzyl 1-benzyl-2-oxo-1,2-dihydroquinoline-4-carboxylate

Abstract

In the title quinoline derivative, C24H19NO3, the two benzyl rings are inclined to the quinoline ring mean plane by 74.09 (8) and 89.43 (7)°, and to each other by 63.97 (10)°. The carboxylate group is twisted from the quinoline ring mean plane by 32.2 (2)°. There is a short intramolecular C—H...O contact forming an S(6) ring motif. In the crystal, molecules are linked by bifurcated C—H,H...O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked by C—H...π interactions, forming a supramolecular three-dimensional structure.

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

“…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.…”

“…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.…”

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

“…Furthermore, many studies have shown that quinoline derivatives are good corrosion inhibitors (Douche et al 2020). ISSN 2056-9890 In a continuation of our research work devoted to the syntheses and crystal structures of quinoline derivatives (Bouzian et al, 2019a), we report herein 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.…”

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

“…In this section, Hirshfeld surface analysis of compounds 3 and 4 were done by Crystal Explorer 3.1 program [31] with the help of CIF files (there is no CIF for compound 2). For Hirshfeld surface analysis a general formalism can be given as follows:…”

“…Given the therapeutic properties of these derivatives, the determination of the structural, geometrical and electronic properties by using DFT calculations is essential to know the influence of different substituents on the pharmacological properties of these molecules [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. In continuation of our work on the design and synthesis of new heterocyclic compounds with potential biological activity [27][28][29][30][31][32], in this study, three new quinoline derivatives (2)(3)(4) have been synthesized by alkylation of 2-oxo-1,2-dihydroquinoline-4-carboxylic acid with ethyl acetate bromide under the conditions of liquid-solid phase transfer catalysis. Molecular structure of the synthesized compounds were characterized by FT-IR, 1 H-NMR, 13 C-NMR, mass spectrometry and crystal structure of compound 4 was determined by single crystal Xray diffraction.…”