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Please use this identifier to cite or link to this item: http://hdl.handle.net/10481/38791

Title: Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin
Authors: Nieto, Carla I.
Cabildo, María Pilar
Cornago, María Pilar
Sanz, Dionisia
Claramount, Rosa M.
Torralba, María del Carmen
Torres, María Rosario
Elguero, José
García, José A.
López Ramírez, Ana
Acuña Castroviejo, Darío
Issue Date: 2015
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.
Sponsorship: This work has been financed by Ministerio de Ciencia e Innovación (CTQ2010-16122) and Ministerio de Economía y Competitividad of Spain (CTQ2014-56833-R, RD12/0043/0005, and PI13-00981) and Comunidad Autónoma de Madrid (Project MADRISOLAR2, ref. S2009/PPQ-1533). One of us (C. I. Nieto) is indebted to UNED for a predoctoral fellowship (FPI “Grupos de Investigación” UNED).
Publisher: MDPI
Keywords: NOS inhibitors
Fluorine derivatives
Multinuclear NMR
URI: http://hdl.handle.net/10481/38791
ISSN: 1420-3049
Rights : Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License
Citation: Nieto, C.I.; et al. Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin. Molecules, 20(9): 15643-15665 (2015). []
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