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Fluorination effects on NOS inhibitory activity of pyrazoles related to curcumin

AutorNieto, Carla I.; Elguero, José ; Acuña-Castroviejo, D.
Palabras claveNOS inhibitors
Crystallography
Curcumin
Fluorine derivatives
Multinuclear NMR
Pyrazoles
Tautomerism
Fecha de publicación28-ago-2015
EditorMolecular Diversity Preservation International
CitaciónMolecules 20(9): 15643-15665 (2015)
ResumenA 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 (H, C, F and N) 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-1Hpyrazole (13), is the best inhibitor of iNOS, being also more selective towards the other two isoforms.
URIhttp://hdl.handle.net/10261/137193
DOI10.3390/molecules200915643
Identificadoresdoi: 10.3390/molecules200915643
issn: 1420-3049
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