Comprehensive analysis of crystal structure, spectroscopic properties, quantum chemical insights, and molecular docking studies of two pyrazolopyridine compounds: potential anticancer agents

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dc.contributor.authorPolo-Cuadrado, Efraín
dc.contributor.authorLópez-Cuellar, Lorena
dc.contributor.authorAcosta-Quiroga, Karen
dc.contributor.authorRojas-Peña, Cristian
dc.contributor.authorBrito, Iván
dc.contributor.authorCisterna, Jonathan
dc.contributor.authorTrilleras, Jorge
dc.contributor.authorAlderete, Joel B.
dc.contributor.authorDuarte, Yorley
dc.contributor.authorGutiérrez, Margarita
dc.date.accessioned2025-01-28T15:40:27Z
dc.date.available2025-01-28T15:40:27Z
dc.date.issued2023-11
dc.descriptionIndexación: Scopus
dc.description.abstractIn this study, two pyrazolo[3,4-b]pyridine derivatives (4a and 4b) were grown using a slow evaporation solution growth technique and characterized by FT-IR, HRMS, 1H/13C NMR spectroscopy, and X-ray crystallography. The 4a and 4b structures crystallized in monoclinic and triclinic systems with space groups P21/n and P1̄, respectively. Theoretical calculations were performed at the DFT/B3LYP level for the optimized geometries. The results were in excellent agreement with the experimental data (spectroscopic and XRD). This investigation encompasses molecular modeling studies including Hirshfeld surface analysis, energy framework calculations, and frontier molecular orbital analysis. Intermolecular interactions within the crystal structures of the compounds were explored through Hirshfeld surface analysis, which revealed the notable presence of hydrogen bonding and hydrophobic interactions. This insight provides valuable information on the structural stability and potential solubility characteristics of these compounds. The research was extended to docking analysis with eight distinct kinases (BRAF, HER2, CSF1R, MEK2, PDGFRA, JAK, AKT1, and AKT2). The results of this analysis demonstrate that both 4a and 4b interact effectively with the kinase-binding sites through a combination of hydrophobic interactions and hydrogen bonding. Compound 4a had the best affinity for proteins; this is related to the fact that the compound is not rigid and has a small size, allowing it to sit well at any binding site. This study contributes to the advancement of kinase inhibitor research and offers potential avenues for the development of new therapeutic agents for cancer treatment. © 2023 The Royal Society of Chemistry.
dc.description.urihttps://pubs.rsc.org/en/content/articlelanding/2023/ra/d3ra04874h#fn1
dc.identifier.citationRSC Advances. Volume 13, Issue 43, Pages 30118 - 30128. 16 October 2023
dc.identifier.doi10.1039/d3ra04874h
dc.identifier.issn2046-2069
dc.identifier.urihttps://repositorio.unab.cl/handle/ria/63324
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.rights.licenseAttribution-NonCommercial 3.0 Unported Deed (CC BY-NC 3.0)
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/
dc.subjectBinding Energy
dc.subjectBinding Sites
dc.subjectComplexation
dc.subjectCrystal Structure
dc.subjectEnzymes
dc.subjectHydrogen bonds
dc.subjectHydrophobicity
dc.subjectMolecular Modeling
dc.subjectMolecular Orbitals
dc.subjectNuclear Magnetic Resonance Spectroscopy
dc.subjectSpectroscopic Analysis
dc.subjectX Ray Crystallography
dc.subjectAnticancer Agents
dc.titleComprehensive analysis of crystal structure, spectroscopic properties, quantum chemical insights, and molecular docking studies of two pyrazolopyridine compounds: potential anticancer agents
dc.typeArtículo
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