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Design, Synthesis, and Biological Evaluation of Novel Fluorinated Ethanolamines

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Design, Synthesis, and Biological Evaluation of Novel Fluorinated Ethanolamines

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dc.contributor.author Fustero, Santos es_ES
dc.contributor.author Cuñat, Ana C. es_ES
dc.contributor.author Flores, Sonia es_ES
dc.contributor.author Baez, Claribel es_ES
dc.contributor.author Oliver, Judit es_ES
dc.contributor.author Cynamon, Michael es_ES
dc.contributor.author Gütschow, Michael es_ES
dc.contributor.author Mertens, Matthias D. es_ES
dc.contributor.author Delgado, Oscar es_ES
dc.contributor.author Tresadem, Gary es_ES
dc.contributor.author Trabanco, Andrés A. es_ES
dc.date.accessioned 2013-11-11T12:48:41Z
dc.date.issued 2011-12-23
dc.identifier.issn 0947-6539
dc.identifier.uri http://hdl.handle.net/10251/33420
dc.description.abstract The preparation of novel fluorinated allylamines and their use as key fragments for the stereoselective synthesis of hydroxyethyl secondary amine (HEA)-type peptidomimetics is described. Our strategy employs chiral sulfinyl imines as synthesis intermediates, by treatment of hemiaminal precursors with two equivalents of vinylmagnesium bromide. The subsequent oxidation of the allylic amines to the corresponding epoxides was achieved by treatment with methyl(trifluoromethyl)dioxirane. Finally, epoxide ring opening with a range of nitrogen nucleophiles provided a library of HEA-derived peptidomimetics with a phenyldifluoromethylene moiety. The biological evaluation of these derivatives revealed compounds with remarkable BACE1 inhibitory activity. Docking studies revealed the influence of the fluorine atoms in the binding mode of the synthesized ligands. Furthermore, the biological evaluation of our final products and synthesis intermediates led to the discovery of compounds with antimicrobial activity against Mycobacterium and Nocardia species. es_ES
dc.format.extent 13 es_ES
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Antimicrobials es_ES
dc.subject BACE1 es_ES
dc.subject Ethanolamines es_ES
dc.subject Fluorine es_ES
dc.subject Peptidomimetics es_ES
dc.title Design, Synthesis, and Biological Evaluation of Novel Fluorinated Ethanolamines es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1002/chem.201102078
dc.rights.accessRights Cerrado es_ES
dc.description.bibliographicCitation Fustero, S.; Cuñat, AC.; Flores, S.; Baez, C.; Oliver, J.; Cynamon, M.; Gütschow, M.... (2011). Design, Synthesis, and Biological Evaluation of Novel Fluorinated Ethanolamines. Chemistry - A European Journal. 17:14772-14784. doi:10.1002/chem.201102078 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1002/chem.201102078 es_ES
dc.description.upvformatpinicio 14772 es_ES
dc.description.upvformatpfin 14784 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 17 es_ES
dc.relation.senia 241513
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