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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Fecha
2023-11
Profesor/a Guía
Facultad/escuela
Idioma
en
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Editor
Royal Society of Chemistry
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Licencia CC
Attribution-NonCommercial 3.0 Unported Deed (CC BY-NC 3.0)
Licencia CC
https://creativecommons.org/licenses/by-nc/3.0/
Resumen
In 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.
Notas
Indexación: Scopus
Palabras clave
Binding Energy, Binding Sites, Complexation, Crystal Structure, Enzymes, Hydrogen bonds, Hydrophobicity, Molecular Modeling, Molecular Orbitals, Nuclear Magnetic Resonance Spectroscopy, Spectroscopic Analysis, X Ray Crystallography, Anticancer Agents
Citación
RSC Advances. Volume 13, Issue 43, Pages 30118 - 30128. 16 October 2023
DOI
10.1039/d3ra04874h