Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin

Nieto Gómez, Carla Isabel, Cabildo Miranda, María del Pilar, Cornago, María del Pilar, Sanz, D., Claramunt, R. M., Torralba, M. Carmen, Rosario Torres, M., Elguero, J., Garcia, J. A., Lopez, A. y Acuña-Castroviejo, Darío . (2015) Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin. Molecules

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Título Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin
Autor(es) Nieto Gómez, Carla Isabel
Cabildo Miranda, María del Pilar
Cornago, María del Pilar
Sanz, D.
Claramunt, R. M.
Torralba, M. Carmen
Rosario Torres, M.
Elguero, J.
Garcia, J. A.
Lopez, A.
Acuña-Castroviejo, Darío
Materia(s) Química
Abstract 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.
Palabras clave NOS inhibitors
pyrazoles
tautomerism
fluorine derivatives
curcumin
crystallography
multinuclear NMR
Editor(es) MDPI
Fecha 2015-08-28
Formato application/pdf
Identificador bibliuned:DptoQOyBO-FCIE-Articulos-Cinieto-0002
http://e-spacio.uned.es/fez/view/bibliuned:DptoQOyBO-FCIE-Articulos-Cinieto-0002
DOI - identifier 10.3390/molecules200915643
ISSN - identifier 1420-3049
Nombre de la revista Molecules
Número de Volumen 20
Número de Issue 9
Página inicial 15643
Página final 15665
Publicado en la Revista Molecules
Idioma eng
Versión de la publicación publishedVersion
Tipo de recurso Article
Derechos de acceso y licencia http://creativecommons.org/licenses/by/4.0
info:eu-repo/semantics/openAccess
Tipo de acceso Acceso abierto
Notas adicionales The registered version of this article, first published in Molecules, is available online at the publisher's website: https://doi.org/10.1080/0309877X.2019.1571174
Notas adicionales La versión registrada de este artículo, publicado por primera vez en Molecules, está disponible en línea en el sitio web del editor: MDPI https://doi.org/10.3390/molecules200915643

 
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Creado: Wed, 31 Jan 2024, 23:46:11 CET