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http://hdl.handle.net/10261/186804
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Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Amata, Emanuele | es_ES |
dc.contributor.author | Rescifina, Antonio | es_ES |
dc.contributor.author | Prezzavento, Orazio | es_ES |
dc.contributor.author | Arena, Emanuela | es_ES |
dc.contributor.author | Dichiara, Maria | es_ES |
dc.contributor.author | Pittalà, Valeria | es_ES |
dc.contributor.author | Montilla-García, Ángeles | es_ES |
dc.contributor.author | Punzo, Francesco | es_ES |
dc.contributor.author | Merino, Pedro | es_ES |
dc.contributor.author | Cobos, Enrique J. | es_ES |
dc.contributor.author | Marrazzo, Agostino | es_ES |
dc.date.accessioned | 2019-07-25T07:05:45Z | - |
dc.date.available | 2019-07-25T07:05:45Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | Journal of Medicinal Chemistry 61(1): 372-384 (2018) | es_ES |
dc.identifier.issn | 0022-2623 | - |
dc.identifier.uri | http://hdl.handle.net/10261/186804 | - |
dc.description.abstract | Methoxycarbonyl-1-phenyl-2-cyclopropylmethyl based derivatives cis-(+)-1a [cis-(+)-MR200], cis-(-)-1a [cis-(-)-MR201], and trans-(±)-1a [trans-(±)-MR204], have been identified as new potent sigma (σ) receptor ligands. In the present paper, novel enantiomerically pure analogues were synthesized and optimized for their σ receptor affinity and selectivity. Docking studies rationalized the results obtained in the radioligand binding assay. Absolute stereochemistry was unequivocally established by X-ray analysis of precursor trans-(+)-5a as camphorsulfonyl derivative 9. The most promising compound, trans-(+)-1d, showed remarkable selectivity over a panel of more than 15 receptors as well as good chemical and enzymatic stability in human plasma. An in vivo evaluation evidenced that trans-(+)-1d, in contrast to trans-(-)-1d, cis-(+)-1d, or cis-(-)-1d, which behave as σ1 antagonists, exhibited a σ1 agonist profile. These data clearly demonstrated that compound trans-(+)-1d, due to its σ1 agonist activity and favorable receptor selectivity and stability, provided an useful tool for the study of σ1 receptors. | es_ES |
dc.description.sponsorship | This work was supported by Research Funding for University (FIR) 2014 project code 108D20.This study was partially supported by the Spanish Ministry of Economy and Competitiveness (grant SAF2016-80540-R), the Junta de Andalucia (grant CTS109) and FEDER funds. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-80540-R | es_ES |
dc.rights | closedAccess | es_ES |
dc.title | (+)-Methyl (1R,2S)-2-{[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]methyl}-1-phenylcyclopropanecarboxylate [(+)-MR200] derivatives as potent and selective sigma receptor ligands: Stereochemistry and pharmacological gands: Stereochemistry and Pharmacological propertiesProperties | es_ES |
dc.type | artículo | es_ES |
dc.identifier.doi | 10.1021/acs.jmedchem.7b01584 | - |
dc.description.peerreviewed | Peer reviewed | es_ES |
dc.relation.publisherversion | https://doi.org/10.1021/acs.jmedchem.7b01584 | es_ES |
dc.identifier.e-issn | 1520-4804 | - |
dc.contributor.funder | Junta de Andalucía | es_ES |
dc.contributor.funder | Ministerio de Economía y Competitividad (España) | es_ES |
dc.relation.csic | Sí | es_ES |
oprm.item.hasRevision | no ko 0 false | * |
dc.identifier.funder | http://dx.doi.org/10.13039/501100003329 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100011011 | es_ES |
dc.contributor.orcid | Merino, Pedro [0000-0002-2202-3460] | es_ES |
dc.identifier.pmid | 29220177 | - |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.openairetype | artículo | - |
item.cerifentitytype | Publications | - |
item.grantfulltext | none | - |
item.fulltext | No Fulltext | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.languageiso639-1 | en | - |
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