RT Journal Article
T1 Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin
A1 Nieto, Carla
A1 Cabildo, María
A1 Cornago, María
A1 Sanz, Dionisia
A1 Claramunt, Rosa
A1 Torralba Martínez, María Del Carmen
A1 Torres, María del Rosario
A1 Elguero, José
A1 García, José
A1 López, Ana
A1 Acuña Castroviejo, Darío
AB 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.
PB MDPI
SN 1420-3049
YR 2015
FD 2015-08-28
LK https://hdl.handle.net/20.500.14352/23874
UL https://hdl.handle.net/20.500.14352/23874
LA eng
NO Ministerio de Ciencia e Innovación (MICINN)
NO Ministerio de Economía y Competitividad (MINECO)
NO Comunidad de Madrid
DS Docta Complutense
RD 14 dic 2025