Structural and Non‐Covalent Interactions Study of 2‐Pyridone Based Flexible Unsymmetrical Dimer

Singh, Ved Prakash; Dowarah, Jayanta; Lalhruaizela,; Geiger, David K.

doi:10.1002/crat.201900136

Cited by 10 publications

(10 citation statements)

References 21 publications

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“…The C–N bond lengths, that is, C11–N2 and C12–N2 (1.313 and 1.343 Å) and C40–N5 and C39–N5 (1.340 and 1.318 Å), are in good agreement with the values of other 2-pyridone derivatives. − The pyridone ring of both molecules A and B (N2, C8, C9, C11, C12, and C14 in molecule A and N5, C36, C37, C39, C40, and C42 in molecule B ) is almost planar as the deviation of these atoms from the mean plane of the ring is very low. Moreover, the sum of the angles about those atoms is almost 360°.…”

Section: Results and Discussionsupporting

confidence: 67%

Synthesis of a Pyridone-Based Phthalimide Fleximer and Its Characterization and Supramolecular Property Evaluation

et al. 2022

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In this study, a novel pyridone-based phthalimide fleximer, that is, ethyl 5-cyano-6-(3-(1,3-dioxoisoindolin-2-yl)propoxy)-4-(3-methoxyphenyl)-2-methylnicotinate, was synthesized, and its structure was established by the single-crystal X-ray diffraction method. The supramolecular self-assembly of the titled compound through noncovalent interactions was then investigated thoroughly. The titled compound crystallized with two symmetry-independent molecules ( A and B , Z ′ = 2). In agreement with experimental observations, our density functional theory calculations also showed that the titled compound has a flexible motif and can occur in various conformations, including molecules A and B . The investigation of the supramolecular framework revealed that the molecules are notably bound by the nonclassical C–H···O and C–H···N hydrogen bonds and C–H···π interactions. Hirshfeld surface analysis was carried out to quantify the various intermolecular interactions. The dual anti-inflammatory activity of the tilted compound was also explored by molecular docking in the active sites of 5-LOX and COX-2 receptors, which revealed good binding affinities of −9.0 and −8.6 kcal/mol, respectively.

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Section: Results and Discussionsupporting

confidence: 67%

Synthesis of a Pyridone-Based Phthalimide Fleximer and Its Characterization and Supramolecular Property Evaluation

et al. 2022

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“…The 4H-pyrans (10 mmol) and excess formic acid (20 mL) refluxed at 115 °C for 3-4 h. After the reaction, the formic acid was reduced under a rotary evaporator, and the residue obtained was recrystallized in methanol to obtain pure products (1)(2)(3)(4). This alternative method is more straightforward, convenient, and favorable than method A.…”

Section: Methods Bmentioning

confidence: 99%

Non‐Covalent Interactions in the Self‐Assembly of Dihydropyridone Supramolecules and In Vitro Anti‐Cancer Assessment in Human Lung Adenocarcinoma Cell Line (A549)

et al. 2023

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The synthesis of dihydropyridone derivatives has been reported by ring rearrangement of pyrans using iodine and formic acid as a catalyst separately. Dihydropyridones were crystallized subjected for single-crystal X-ray crystallography to acquire their structural parameters. The different non-covalent interactions involved within the supramolecular systems were studied and validated using Hirshfeld surface plot analysis. NÀ H•••O interactions between the lactam group dominate. Still, other non-covalent interactions such as CÀ Hand lone pair•••π systems act as the driving force in facilitating the self-assembly of the dihydropyridone supramolecules. The synthesized compounds were analyzed by in vitro techniques using human lung adenocarcinoma (A549) to evaluate their cytotoxic activities. Ethyl 4-(4-chlorophenyl)-5cyano-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate has shown the highest cytotoxicity among all the synthesized compounds. Molecular recognition properties of the dihydropyridone compounds were also studied, employing molecular docking tools to gain insight into the binding mode inside the allosteric binding pocket of the Eg5 protein through noncovalent interactions.

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“…Crystal packing of molecules stabilized via various non-covalent interactions. In the packing diagram, four molecules arranged in two planes in two groups just perpendicular to the each other due to the presence of intermolecular edge to face C (29) (Figure 3 and Table 3). These interactions are present between a similar ring of two molecules.…”

Section: Crystal Structure Analysismentioning

confidence: 99%

Design, synthesis, in silico analysis with PPAR‐γ receptor and study of non‐covalent interactions in unsymmetrical heterocyclic/phenyl fleximer

Singh

Dowarah

Marak

et al. 2020

J Chinese Chemical Soc

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This work deals with the design, synthesis, in silico analysis, crystallization, and the interpretation 2‐cyano‐3‐{4‐[2‐(phthalimid‐nyl)‐propoxy]‐phenyl}‐acrylic acid ethyl ester (7). Analog 7 is designed based on rosiglitazone. The quantitative analysis of Compound 7 has been performed through single‐crystal X‐Ray Diffraction (XRD) and Hirshfeld surface analysis. Fleximer 7 has studied the role of flexibility in non‐covalent interactions and binding affinity with PPAR‐γ receptors. Both phthalimide ring and phenyl rings are linked with propylene linker. 2‐cyano‐3‐{4‐[2‐(phthalimid‐nyl)‐propoxy]‐phenyl}‐acrylic acid ethyl ester has Z = 8 in the crystal packing and stabilized by intermolecular non‐covalent interactions like CH…O, CH…N, CH…л, and л…л, and so forth.

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Structural and Non‐Covalent Interactions Study of 2‐Pyridone Based Flexible Unsymmetrical Dimer

Cited by 10 publications

References 21 publications

Synthesis of a Pyridone-Based Phthalimide Fleximer and Its Characterization and Supramolecular Property Evaluation

Synthesis of a Pyridone-Based Phthalimide Fleximer and Its Characterization and Supramolecular Property Evaluation

Non‐Covalent Interactions in the Self‐Assembly of Dihydropyridone Supramolecules and In Vitro Anti‐Cancer Assessment in Human Lung Adenocarcinoma Cell Line (A549)

Design, synthesis, in silico analysis with PPAR‐γ receptor and study of non‐covalent interactions in unsymmetrical heterocyclic/phenyl fleximer

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