Publicación:
Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin

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Fecha
2015-08-28
Autores
Cabildo Miranda, Mª del Pilar
Cornago, María del Pilar
Sanz, D.
Claramunt, R. M.
Torralba, M. Carmen
Torres, M. Rosario
Elguero, J.
Garcia, J. A.
Acuña Castroviejo, Darío
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info:eu-repo/semantics/openAccess
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MDPI
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Resumen
A series of new (E)-3(5)-[β-(aryl)-ethenyl]-5(3)-phenyl-1H-pyrazoles bearing fluorine atoms at different positions of the aryl group have been synthesized starting from the corresponding β-diketones. All compounds have been characterized by elemental analysis, DSC as well as NMR (1H, 13C, 19F and 15N) spectroscopy in solution and in solid state. Three structures have been solved by X-ray diffraction analysis, confirming the tautomeric forms detected by solid state NMR. The in vitro study of their inhibitory potency and selectivity on the activity of nNOS and eNOS (calcium-calmodulin dependent) as well as iNOS (calcium-calmodulin independent) isoenzymes is presented. A qualitative structure–activity analysis allowed the establishment of a correlation between the presence/absence of different substituents with the inhibition data proving that fluorine groups enhance the biological activity. (E)-3(5)-[β-(3-Fluoro-4-hydroxyphenyl)-ethenyl]-5(3)-phenyl-1H-pyrazole (13), is the best inhibitor of iNOS, being also more selective towards the other two isoforms.
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Categorías UNESCO
Palabras clave
NOS inhibitors, pyrazoles, tautomerism, fluorine derivatives, curcumin, crystallography, multinuclear NMR
Citación
Centro
Facultad de Ciencias
Departamento
Química Orgánica y Bio-Orgánica
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Grupo de innovación
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Cátedra