Study of supramolecular self-assembly of pyridone and dihydropyridone co-crystal: Synthesis, crystal structure, Hirshfeld surface, DFT and molecular docking studies

Lalhruaizela,; Marak, Brilliant N.; Gogoi, Dipanta; Dowarah, Jayanta; Sran, Balkaran Singh; Pachuau, Zodinpuia; Singh, Ved Prakash

doi:10.1016/j.molstruc.2021.130214

Cited by 12 publications

(23 citation statements)

References 48 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. 46 − 48 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 Discussionmentioning

confidence: 99%

“…Compound 9 was synthesized according to the method reported in our previous paper. 48 In a 100 mL round-bottom flask, 2-pyridone derivative 9 (0.0068 mmol) was dissolved in dimethylformamide (DMF), and potassium carbonate (0.0072 mmol) was added and stirred for 20 min. After that, 2-(3-bromopropyl)isoindoline-1,3-dione ( 11 ) (0.0068 mol) was added and stirred for 12 h. The progress of the reaction was monitored using thin-layer chromatography (30% EtOAc in hexane).…”

Section: Experimental Sectionmentioning

confidence: 99%

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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 Discussionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

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

et al. 2022

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“… 28 The crystal structures of the human kinesin Eg5 and survivin protein were retrieved from the RSCB protein data bank (PDB id: and , respectively). 29 The protein preparation was done in autodock tools 30 by removing co-crystallized ligands, embedded water molecules, and cofactors. It was further processed by adding polar hydrogens and saved in the pdbqt format.…”

Section: Experimental Designmentioning

confidence: 99%

Green synthesis, structural analysis and anticancer activity of dihydropyrimidinone derivatives

et al. 2021

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“…These interactions, including C-H…N, CÀ H…O, CÀ H…π, and π…π, etc., are fundamental cohesive and adhesive forces in the supramolecular self-assembly of molecules. [5,6] Although weak interactions are weaker than hydrogen, ionic, and coordination bonds, they play a crucial role in non-charged and nonpolar compounds and amino acid residues. [7] These strong and weak interactions play a significant role in forming higher-order structures of complex biopolymers like proteins and supramolecular assembly.…”

Section: Introductionmentioning

confidence: 99%

“…The non‐covalent interaction is a general term encompassing hydrogen bonds, ionic bonds, and other weak interactions such as van der Walls and hydrophobic bonds. These interactions, including C–H…N, C−H…O, C−H…π, and π…π, etc., are fundamental cohesive and adhesive forces in the supramolecular self‐assembly of molecules [5,6] . Although weak interactions are weaker than hydrogen, ionic, and coordination bonds, they play a crucial role in non‐charged and nonpolar compounds and amino acid residues [7] .…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and Molecular Docking of 4H‐Pyrans

et al. 2021

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In this study, a series of four 4H-pyrans were synthesized by multicomponent reaction, crystallized, and single-crystal X-ray diffraction was used to obtain their molecular geometries. The supramolecular assembly of the molecules through noncovalent interactions was then studied and demonstrated. The weak intermolecular interactions in the molecular packing of compounds were further validated through Hirshfeld surface analysis. The synthesized compounds' biological activity was predicted in Pass prediction. A molecular docking study was employed to validate its activity by analyzing its binding affinity and mode in the binding pocket of the beta-adrenoreceptors (β 1 -AR and β 2 -AR). Results showed that ethyl 6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-4H-pyran-3-carboxylate have good antiischemic activity and binding affinity to both the adrenoreceptors. This study further demonstrated the importance of non-covalent intermolecular interactions of 4H-pyrans in the formation of supramolecular self-assembly and contributions of weak interactions in binding affinity towards the target receptor. The studied compounds displayed distinctive intermolecular interactions of NÀ H…N, NÀ H…O hydrogen-bonding patterns and CÀ H…π and π…π close contact interactions.

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Study of supramolecular self-assembly of pyridone and dihydropyridone co-crystal: Synthesis, crystal structure, Hirshfeld surface, DFT and molecular docking studies

Cited by 12 publications

References 48 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

Green synthesis, structural analysis and anticancer activity of dihydropyrimidinone derivatives

Multicomponent Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and Molecular Docking of 4H‐Pyrans

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