Ethyl 2,6-bis(4-chlorophenyl)-4-(4-fluoroanilino)-1-(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

Anthal, Sumati; Brahmachari, Goutam; Das, Suvankar; Kant, Rajni; Gupta, Vivek K.

doi:10.1107/s1600536813006090

Cited by 2 publications

(2 citation statements)

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“…The reference codes of these nine structures are COJCIP, 20 GATCUB, 21 KAGSAQ, 22 KAGSEU, 17 LETBET, 23 MEJTAZ, 24 MEWTOZ, 25 MONVAO, 26 and WIHCOH. 27 The S (6) intramolecular H-bonding loop was formed through intramolecular N–H···O bonding between the amino group and carbonyl O-atom in all the nine crystal structures of the CSD. The same H-bonded loop is formed in FTEAA by the intramolecular H-bonding between the amino group and carbonyl O-atom.…”

Section: Resultsmentioning

confidence: 93%

“…The Cambridge structural database (CSD 9) provides nine crystal structures that are closely related to the crystal structure of FTEAA . The reference codes of these nine structures are COJCIP, GATCUB, KAGSAQ, KAGSEU, LETBET, MEJTAZ, MEWTOZ, MONVAO, and WIHCOH . The S (6) intramolecular H-bonding loop was formed through intramolecular N–H···O bonding between the amino group and carbonyl O-atom in all the nine crystal structures of the CSD.…”

Section: Resultsmentioning

confidence: 99%

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Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

et al. 2022

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Ethyl 4-(4-fluorophenylamino)-2,6-bis(4-(trifluoromethyl)phenyl)-1-(4-fluoro-phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate ( FTEAA ) has been synthesized efficiently in an iodine-catalyzed five-component reaction of 4-fluoroaniline, 4-trifluoromethyl benzaldehyde, and ethyl acetoacetate in methanol at 55 °C for 12 h. Various spectro-analytical techniques such as 1 H and 13 C NMR and Fourier-transform infrared spectroscopy have validated the structure of FTEAA . Further confirmation of the structure of FTEAA has been established on the basis of single-crystal X-ray diffraction analysis. The supramolecular assembly of FTEAA in terms of strong and comparatively weak noncovalent interactions is fully investigated by Hirshfeld surface analysis, the interaction energy between pairs of molecules, and energy frameworks. The void analysis is conducted to explore the strength and stability of the crystal structure. Furthermore, molecular docking analysis was computationally performed to see the potential intermolecular interactions between the selected proteins and FTEAA . The binding interaction energies are found to be −8.8 and −9.6 kcal/mol for the proteins MAO-B (PDB ID: 2V5Z ) and MAO-A (PDB ID: 2Z5X ), respectively. These reasonably good binding energies (more negative values) indicate the efficient associations between the FTEAA and target proteins. The proteins and FTEAA were also analyzed for intermolecular interactions. FTEAA and proteins interact in a variety of ways, like conventional hydrogen bonds, carbon–hydrogen bonds, alkyl, π-alkyl, and halide interactions.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

et al. 2022

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Synthesis, crystal structure, Hirshfeld surface analysis, DFT and NBO study of ethyl 1-(4-fluorophenyl)-4-[(4-fluorophenyl)amino]-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Bansal,

Butcher,

Gupta

2023

Acta Cryst E

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The title compound, C32H28F2N2O2, a highly functionalized tetrahydropyridine, was synthesized by a one-pot multi-component reaction of 4-fluoroaniline, ethyl acetoacetate and benzaldehyde at room temperature using sodium lauryl sulfate as a catalyst. The compound crystallizes with two molecules in the asymmetric unit. The tetrahydropyridine ring adopts a distorted boat conformation in both molecules and the dihedral angles between the planes of the fluoro-substituted rings are 77.1 (6) and 77.3 (6)°. The amino group and carbonyl O atom are involved in an intramolecular N—H...O hydrogen bond, thereby generating an S(6) ring motif. In the crystal, molecules are linked by C—H...F hydrogen bonds forming a three-dimensional network and C—H...π interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (47.9%), C...H/H...C (30.7%) and F...H/H...F (12.4%) contacts. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6-311+G(2d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was used to determine the energy gap and the Natural Bond Orbital (NBO) analysis was done to study donor–acceptor interconnections.

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Ethyl 2,6-bis(4-chlorophenyl)-4-(4-fluoroanilino)-1-(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

Cited by 2 publications

References 19 publications

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

Synthesis, crystal structure, Hirshfeld surface analysis, DFT and NBO study of ethyl 1-(4-fluorophenyl)-4-[(4-fluorophenyl)amino]-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

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