{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,17]],"date-time":"2026-03-17T16:56:42Z","timestamp":1773766602757,"version":"3.50.1"},"reference-count":84,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2015,8,28]],"date-time":"2015-08-28T00:00:00Z","timestamp":1440720000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of new (E)-3(5)-[\u03b2-(aryl)-ethenyl]-5(3)-phenyl-1H-pyrazoles bearing fluorine atoms at different positions of the aryl group have been synthesized starting from the corresponding \u03b2-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\u2013activity 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)-[\u03b2-(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.<\/jats:p>","DOI":"10.3390\/molecules200915643","type":"journal-article","created":{"date-parts":[[2015,9,1]],"date-time":"2015-09-01T10:55:58Z","timestamp":1441104958000},"page":"15643-15665","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin"],"prefix":"10.3390","volume":"20","author":[{"given":"Carla","family":"Nieto","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica y Bio-Org\u00e1nica, Facultad de Ciencias,  Universidad Nacional de Educaci\u00f3n a Distancia, Paseo Senda del Rey, 9, Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda","family":"Cabildo","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica y Bio-Org\u00e1nica, Facultad de Ciencias,  Universidad Nacional de Educaci\u00f3n a Distancia, Paseo Senda del Rey, 9, Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda","family":"Cornago","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica y Bio-Org\u00e1nica, Facultad de Ciencias,  Universidad Nacional de Educaci\u00f3n a Distancia, Paseo Senda del Rey, 9, Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dionisia","family":"Sanz","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica y Bio-Org\u00e1nica, Facultad de Ciencias,  Universidad Nacional de Educaci\u00f3n a Distancia, Paseo Senda del Rey, 9, Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosa","family":"Claramunt","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica y Bio-Org\u00e1nica, Facultad de Ciencias,  Universidad Nacional de Educaci\u00f3n a Distancia, Paseo Senda del Rey, 9, Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda","family":"Torralba","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica I and CAI de Difracci\u00f3n de Rayos-X,  Facultad de Ciencias Qu\u00edmicas, Universidad Complutense de Madrid (UCM), Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda","family":"Torres","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica I and CAI de Difracci\u00f3n de Rayos-X,  Facultad de Ciencias Qu\u00edmicas, Universidad Complutense de Madrid (UCM), Madrid 28040, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9","family":"Elguero","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica M\u00e9dica, Centro de Qu\u00edmica Org\u00e1nica \u201cManuel Lora-Tamayo\u201d, CSIC,  Juan de la Cierva, 3, Madrid 28006, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9","family":"Garc\u00eda","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n Biom\u00e9dica, Parque Tecnol\u00f3gico de Ciencias de la Salud,  Universidad de Granada, Avda. del Conocimiento s\/n, Armilla, 18100 Granada, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ana","family":"L\u00f3pez","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n Biom\u00e9dica, Parque Tecnol\u00f3gico de Ciencias de la Salud,  Universidad de Granada, Avda. del Conocimiento s\/n, Armilla, 18100 Granada, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9680-1560","authenticated-orcid":false,"given":"Dar\u00edo","family":"Acu\u00f1a-Castroviejo","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n Biom\u00e9dica, Parque Tecnol\u00f3gico de Ciencias de la Salud,  Universidad de Granada, Avda. del Conocimiento s\/n, Armilla, 18100 Granada, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2015,8,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6180","DOI":"10.1016\/j.bmc.2009.07.067","article-title":"Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation","volume":"17","author":"Claramunt","year":"2009","journal-title":"Bioorg. 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