Artículo
X-ray characterization, Hirshfeld surface analysis, DFT calculations,in vitroandin silicolipoxygenase inhibition (LOX) studies of dichlorophenyl substituted 3-hydroxy-chromenones
Ahmed, Muhammad Naeem; Ghias, Mehreen; Shah, Syed Wadood Ali; Shoaib, Mohammad; Tahir, Muhammad Nawaz; Ashfaq, Muhammad; Ibrahim, Mahmoud A. A.; Andleeb, Hina; Gil, Diego Mauricio
; Frontera, Antonio
![Icon](/themes/CONICETDigital/images/conicet.png)
Fecha de publicación:
09/2021
Editorial:
Royal Society of Chemistry
Revista:
New Journal of Chemistry
ISSN:
1144-0546
e-ISSN:
1369-9261
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
This work reports the synthesis and X-ray characterization of three dichlorophenyl substituted 3-hydroxy-chromen-4-one derivatives,i.e., 2-(2,4-dichlorophenyl)-3-hydroxy-4H-chromen-4-one (1), 2-(2,3-dichlorophenyl)-3-hydroxy-4H-chromen-4-one (2), and 2-(2,6-dichlorophenyl)-3-hydroxy-4H-chromen-4-one (3). The solid-state architecture of these three isomers is quite different due to the large influence of the Cl-substituents on the dihedral angle between the phenyl and chromenone rings. The different assemblies and synthons have been studied using Hirshfeld surface analysis and by computing their interaction energies and different contributions (electrostatic, polarization, dispersion and repulsion). Furthermore, only one isomer forms directional halogen bonding interactions (C-Cl⋯O) that have been analyzed using MEP surface calculations and characterized using a combination of QTAIM and NCIplot index computational methods. The ability to form halogen bonds depending on the substitution has also been analyzed. The docking results showed that compound1forms strong binding interactions with soybean lipoxygenase followed by compounds2and3. The molecular docking results are in good agreement with the bioactivity data of1-3(IC50values) against lipoxygenase.
Palabras clave:
CHROMENONES
,
DFT CALCULATIONS
,
HIRSHFELD SURFACE ANALYSIS
,
DOCKING STUDIES
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Licencia
Identificadores
Colecciones
Articulos(INBIOFAL)
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Citación
Ahmed, Muhammad Naeem; Ghias, Mehreen; Shah, Syed Wadood Ali; Shoaib, Mohammad; Tahir, Muhammad Nawaz; et al.; X-ray characterization, Hirshfeld surface analysis, DFT calculations,in vitroandin silicolipoxygenase inhibition (LOX) studies of dichlorophenyl substituted 3-hydroxy-chromenones; Royal Society of Chemistry; New Journal of Chemistry; 45; 42; 9-2021; 19928-19940
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