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http://hdl.handle.net/10261/174640
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Nieto, Carla I. | - |
dc.contributor.author | Cornago, M. P. | - |
dc.contributor.author | Cabildo, M. Pilar | - |
dc.contributor.author | Sanz, Dionisia | - |
dc.contributor.author | Claramunt, Rosa M. | - |
dc.contributor.author | Torralba, M. Carmen | - |
dc.contributor.author | Elguero, José | - |
dc.date.accessioned | 2019-01-24T10:22:00Z | - |
dc.date.available | 2019-01-24T10:22:00Z | - |
dc.date.issued | 2019 | - |
dc.identifier | doi: 10.1016/j.jfluchem.2018.12.012 | - |
dc.identifier | issn: 0022-1139 | - |
dc.identifier.citation | Journal of Fluorine Chemistry 219: 39-49 (2019) | - |
dc.identifier.uri | http://hdl.handle.net/10261/174640 | - |
dc.description.abstract | The purpose of this work is to prepare a series of isoxazoles bearing phenyl and 4’-hydroxy-styryl substituents at position 3 and 5; besides the phenyl group of the styryl residue bears one or two fluorine substituents. They were prepared to study their structure in the solid state and in solution by X-ray crystallography and solid-state NMR (SSNMR) for the solid state and NMR for the solution. The reaction of hydroxylamine with hemi-curcuminoid β-diketones affords two isomeric isoxazoles we have named series a (3-phenyl) and b (5-phenyl) that have been identified and characterized. Four pairs have been prepared that in three cases bear one or two fluorine atoms. Three X-ray structures have been determined 3a, 3b and 5b; 3a crystallizes without solvent, 3b crystallizes with a water molecule hydrogen-bonded to a phenolic OH, finally 5b crystallizes as a solvate with a methanol molecule hydrogen-bonded to the isoxazole N atom. This hydrogen bond results in larger differences between N chemical shifts in DMSO-d solution and in the solid state. The splitting of some signals observed in Cross-Polarization Magic Angle Spinning (CPMAS) C NMR was assigned to J dipolar couplings. The combined use of crystallography and SSNMR affords a complete characterization of isomeric isoxazoles, in particular the assignment of an isoxazole to a or to b series is not a trivial matter. In this work, we describe methods for the synthesis of isoxazoles bearing fluorine substituents that are promising structures for drug discovery. | - |
dc.description.sponsorship | This work was supported by Ministerio de Economía y Competitividad of Spain (CTQ2014-56833-R and CTQ2015-63997-C2- 2-P) and Comunidad Autónoma de Madrid (Project MADRISOLAR2, ref. S2009/PPQ-1533). Carla I. Nieto is indebted to UNED for a predoctoral contract >FPI Grupos de Investigación>. | - |
dc.publisher | Elsevier | - |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-56833-R | - |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-63997-C2-2-P | - |
dc.rights | closedAccess | - |
dc.subject | Hemi-curcuminoids | - |
dc.subject | X-ray crystallography | - |
dc.subject | Solid-state NMR | - |
dc.subject | Fluorinated isoxazoles | - |
dc.subject | Isoxazole | - |
dc.title | Synthesis, structure and NMR study of fluorinated isoxazoles derived from hemi-curcuminoids | - |
dc.type | artículo | - |
dc.identifier.doi | 10.1016/j.jfluchem.2018.12.012 | - |
dc.relation.publisherversion | http://dx.doi.org/10.1016/j.jfluchem.2018.12.012 | - |
dc.date.updated | 2019-01-24T10:22:01Z | - |
dc.description.version | Peer Reviewed | - |
dc.language.rfc3066 | eng | - |
dc.contributor.funder | Ministerio de Economía, Industria y Competitividad (España) | - |
dc.contributor.funder | Comunidad de Madrid | - |
dc.relation.csic | Sí | - |
dc.identifier.funder | http://dx.doi.org/10.13039/100012818 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100010198 | es_ES |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.cerifentitytype | Publications | - |
item.grantfulltext | none | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | No Fulltext | - |
item.openairetype | artículo | - |
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