Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin



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Nieto, Carla and Cabildo, María and Cornago, María and Sanz, Dionisia and Claramunt, Rosa and Torralba Martínez, María del Carmen and Torres, María del Rosario and Elguero, José and García, José and López, Ana and Acuña-Castroviejo, Darío (2015) Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin. Molecules, 20 (9). pp. 15643-15665. ISSN 1420-3049

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Official URL: https://doi.org/10.3390/molecules200915643


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.

Item Type:Article
Uncontrolled Keywords:NOS inhibitors; pyrazoles; tautomerism; fluorine derivatives; curcumin; crystallography; multinuclear NMR
Subjects:Sciences > Chemistry > Chemistry, Inorganic
ID Code:66549
Deposited On:30 Jun 2021 14:26
Last Modified:06 Jul 2021 09:14

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