Supramolecular architectures in dihydropyridones: Synthesis, crystal structure, Hirshfeld analysis, cytotoxicity and in silico studies

Lalhruaizela,; Patel, Devanshi; Marak, Brilliant N.; Dowarah, Jayanta; Sran, Balkaran Singh; Yadav, Umesh C. S.; Singh, Ved Prakash

doi:10.1016/j.molstruc.2021.131671

Cited by 8 publications

(12 citation statements)

References 27 publications

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“… 1 Moreover, understanding molecular recognition in biological systems requires an understanding of noncovalent interactions. 3 − 5 The self-assembly of molecules through noncovalent interactions has resulted in remarkable supramolecular architectures with a wide range of applications. 6 , 7 For instance, the host–guest interaction of cyclodextrins with drugs allows cyclodextrins to encapsulate drug molecules and deliver them to specific targets.…”

Section: Introductionmentioning

confidence: 99%

“… 21 Furthermore, C–H···lp (lone pair), C–H···π, and π···π interactions also act as cohesive forces in the supramolecular assembly of molecules. 3 , 22 Understanding these forces is also important for solid-state materials with desirable properties in supramolecular chemistry. 3 , 23 …”

Section: Introductionmentioning

confidence: 99%

“… 3 , 22 Understanding these forces is also important for solid-state materials with desirable properties in supramolecular chemistry. 3 , 23 …”

Section: Introductionmentioning

confidence: 99%

“…Thus, understanding intermolecular interactions is important in crystal engineering and supramolecular chemistry. , It also plays an important role in other areas such as biochemistry, protein folding, drug design, and material science . Moreover, understanding molecular recognition in biological systems requires an understanding of noncovalent interactions. − The self-assembly of molecules through noncovalent interactions has resulted in remarkable supramolecular architectures with a wide range of applications. , For instance, the host–guest interaction of cyclodextrins with drugs allows cyclodextrins to encapsulate drug molecules and deliver them to specific targets.…”

Section: Introductionmentioning

confidence: 99%

“…Generally, noncovalent interactions refer to hydrogen bonds; − halogen bonds; , ionic bonds; − and weak interactions such as van der Waals, hydrophobic, , aromatic π–stacking interactions, and so forth. , These powerful driving forces lead to diverse interactions between molecules such as hydrogen bonds of the types O–H···O, N–H···O, C–H···N, and C–H···O and other weaker interactions of the types I···I, O···I, N···Cl, C···H, C···C, and so forth . Furthermore, C–H···lp (lone pair), C–H···π, and π···π interactions also act as cohesive forces in the supramolecular assembly of molecules. , Understanding these forces is also important for solid-state materials with desirable properties in supramolecular chemistry. , …”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“… 3 , 22 Understanding these forces is also important for solid-state materials with desirable properties in supramolecular chemistry. 3 , 23 …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

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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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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Synthesis of Spirooxindoles and Study of their Self‐Assembly features; Hirshfeld Surface, Energy Framework andIn Silicoanalysis

et al. 2023

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In this study, the 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitrile derivatives were synthesized, crystallized, and their molecular geometries were established by the SCXRD method. The significance of weak intermolecular interactions in the self‐assembly of 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitriles was then investigated. The supramolecular framework analysis indicated that 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitriles establish their network in self‐assembly mainly by N−H⋅⋅⋅O, N−H⋅⋅⋅N, C−H⋅⋅⋅O, C−H⋅⋅⋅C, C−H⋅⋅⋅N, and C−H⋅⋅⋅π interactions. The energy framework analysis revealed the dominant contribution of electrostatic energy in the crystal packing of the titled compounds. The PASS prediction of the titled compounds has shown a reasonably good affinity towards Insulin‐regulated aminopeptidase. Further, the molecular docking study with Insulin‐regulated aminopeptidase receptor has shown the higher affinity of the titled compounds to the zinc binding pocket over the other pockets.

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Supramolecular architectures in dihydropyridones: Synthesis, crystal structure, Hirshfeld analysis, cytotoxicity and in silico studies

Cited by 8 publications

References 27 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)

Synthesis of Spirooxindoles and Study of their Self‐Assembly features; Hirshfeld Surface, Energy Framework andIn Silicoanalysis

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