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Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin

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dc.contributor.authorCabildo Miranda, Mª del Pilar
dc.contributor.authorCornago, María del Pilar
dc.contributor.authorSanz del Castillo, Dionisia
dc.contributor.authorClaramunt, R. M.
dc.contributor.authorTorralba, M. Carmen
dc.contributor.authorTorres, M. Rosario
dc.contributor.authorElguero, J.
dc.contributor.authorGarcia, J. A.
dc.contributor.authorAcuña Castroviejo, Darío
dc.contributor.authorNieto Gómez, Carla Isabel
dc.contributor.authorLópez Peláez, Antonio
dc.date.accessioned2024-05-20T11:58:34Z
dc.date.available2024-05-20T11:58:34Z
dc.date.issued2015-08-28
dc.description.abstractA 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.en
dc.description.versionversión publicada
dc.identifier.doihttp://doi.org/10.3390/molecules200915643
dc.identifier.issn1420-3049
dc.identifier.urihttps://hdl.handle.net/20.500.14468/12777
dc.journal.issue9
dc.journal.titleMolecules
dc.journal.volume20
dc.language.isoen
dc.publisherMDPI
dc.relation.centerFacultad de Ciencias
dc.relation.departmentQuímica Orgánica y Bio-Orgánica
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/deed.es
dc.subject.keywordsNOS inhibitors
dc.subject.keywordspyrazoles
dc.subject.keywordstautomerism
dc.subject.keywordsfluorine derivatives
dc.subject.keywordscurcumin
dc.subject.keywordscrystallography
dc.subject.keywordsmultinuclear NMR
dc.titleFluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumines
dc.typejournal articleen
dc.typeartículoes
dspace.entity.typePublication
relation.isAuthorOfPublicationc4e6468b-75c5-452b-bf12-9637dd3519f3
relation.isAuthorOfPublicationc6f94a2a-9f54-48f9-a6f1-3115b17b098d
relation.isAuthorOfPublication5ebad039-e479-483b-9bdb-12e785cb437e
relation.isAuthorOfPublication.latestForDiscoveryc6f94a2a-9f54-48f9-a6f1-3115b17b098d
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