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http://hdl.handle.net/2445/108047
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DC Field | Value | Language |
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dc.contributor.author | Pereira, Nuno A. L. | - |
dc.contributor.author | Sureda, Francesc X. | - |
dc.contributor.author | Pérez Bosch, Maria | - |
dc.contributor.author | Amat Tusón, Mercedes | - |
dc.contributor.author | Santos, Maria M. M. | - |
dc.date.accessioned | 2017-03-07T15:27:28Z | - |
dc.date.available | 2017-03-07T15:27:28Z | - |
dc.date.issued | 2016-08-06 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/2445/108047 | - |
dc.description.abstract | Enantiopure tryptophanol is easily obtained from the reduction of its parent natural amino acid trypthophan (available from the chiral pool), and can be used as chiral auxiliary/inductor to control the stereochemical course of a diastereoselective reaction. Furthermore, enantiopure tryptophanol is useful for the syntheses of natural products or biological active molecules containing the aminoalcohol functionality. In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity as N-Methyl D-Aspartate (NMDA) receptor antagonists. The indolo[2,3-a]quinolizidine scaffold was obtained using the following key steps: (i) a stereoselective cyclocondensation of (S)- or (R)-tryptophanol with appropriate racemic -oxoesters; (ii) a stereocontrolled cyclization on the indole nucleus. The synthesized enantiopure indolo[2,3-a]quinolizidines were evaluated as NMDA receptor antagonists and one compound was identified to be 2.9-fold more potent as NMDA receptor blocker than amantadine (used in the clinic for Parkinson's disease). This compound represents a hit compound for the development of novel NMDA receptor antagonists with potential applications in neurodegenerative disorders associated with overactivation of NMDA receptors. | - |
dc.format.extent | 13 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | MDPI | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.3390/molecules21081027 | - |
dc.relation.ispartof | Molecules, 2016, vol. 21, num. 8, p. 1027-1039 | - |
dc.relation.uri | https://doi.org/10.3390/molecules21081027 | - |
dc.rights | cc-by (c) Pereira, Nuno A. L. et al., 2016 | - |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es | - |
dc.source | Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) | - |
dc.subject.classification | Malalties neurodegeneratives | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.other | Neurodegenerative Diseases | - |
dc.subject.other | Organic synthesis | - |
dc.title | Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 664810 | - |
dc.date.updated | 2017-03-07T15:27:28Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 27509489 | - |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) |
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File | Description | Size | Format | |
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664810.pdf | 1.88 MB | Adobe PDF | View/Open |
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