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dc.contributor.author | Ragusa, Giulio | es_ES |
dc.contributor.author | Gómez-Cañas, María | es_ES |
dc.contributor.author | Morales, Paula | es_ES |
dc.contributor.author | Hurst, D. P. | es_ES |
dc.contributor.author | Deligia, F. | es_ES |
dc.contributor.author | Pazos, Ruth | es_ES |
dc.contributor.author | Pinna, Gerard A. | es_ES |
dc.contributor.author | Fernández-Ruiz, Javier | es_ES |
dc.contributor.author | Goya, Pilar | es_ES |
dc.contributor.author | Reggio, Patricia | es_ES |
dc.contributor.author | Jagerovic, Nadine | es_ES |
dc.contributor.author | García-Arencibia, Moisés | es_ES |
dc.contributor.author | Murineddu, Gabriele | es_ES |
dc.date.issued | 2015 | - |
dc.identifier | doi: 10.1016/j.ejmech.2015.06.057 | - |
dc.identifier | issn: 1768-3254 | - |
dc.identifier | e-issn: 1768-3254 | - |
dc.identifier.citation | European Journal of Medicinal Chemistry 101: 651-667 (2015) | es_ES |
dc.identifier.uri | http://hdl.handle.net/10261/126319 | - |
dc.description.abstract | During the last years, there has been a continuous interest in the development of cannabinoid receptor ligands that may serve as therapeutic agents and/or as experimental tools. This prompted us to design and synthesize analogues of the CB<inf>2</inf> receptor antagonist N-fenchyl-5-(4-chloro-3-methyl-phenyl)-1-(4-methyl-benzyl)-1H-pyrazole-3-carboxamide (SR144528). The structural modifications involved the bioisosteric replacement of the pyrazole ring by a pyrrole ring and variations on the amine carbamoyl substituents. Two of these compounds, the fenchyl pyrrole analogue 6 and the myrtanyl derivative 10, showed high affinity (K<inf>i</inf> in the low nM range) and selectivity for the CB<inf>2</inf> receptor and both resulted to be antagonists/inverse agonists in [<sup>35</sup>S]-GTPγS binding analysis and in an in vitro CB<inf>2</inf> receptor bioassay. Cannabinoid receptor binding data of the series allowed identifying steric constraints within the CB<inf>2</inf> binding pocket using a study of Van der Waals' volume maps. Glide docking studies revealed that all docked compounds bind in the same region of the CB<inf>2</inf> receptor inactive state model. | es_ES |
dc.description.sponsorship | GM acknowledges Regione Autonoma della Sardegna for economic support (grant n. CRP-26417, LR n. 7/2007 and INNOVA.REPOR FESR 2007-2013). PM is recipient of a CSIC fellowship JAEPre- 2010-01119 from Junta para la Ampliacion de Estudios cofinanced by FSE. MGA was recipient of a postdoctoral fellowship from the PICATA Program, CEI-Moncloa. NJ thanks the Spanish Ministry of Economy and Competitivity for the grant SAF2012- 40075, and with JFR the “Programa de Biomedicina, Comunidad de Madrid” (S2011/BMD-2308). | es_ES |
dc.publisher | Elsevier | es_ES |
dc.relation | S2010/BMD-2308/CANNAB | es_ES |
dc.relation.isversionof | Postprint | es_ES |
dc.rights | openAccess | es_ES |
dc.title | Synthesis, pharmacological evaluation and docking studies of pyrrole structure-based CB<inf>2</inf> receptor antagonists | es_ES |
dc.type | artículo | es_ES |
dc.identifier.doi | 10.1016/j.ejmech.2015.06.057 | - |
dc.description.peerreviewed | Peer reviewed | es_ES |
dc.relation.publisherversion | http://dx.doi.org/10.1016/j.ejmech.2015.06.057 | es_ES |
dc.date.updated | 2015-12-02T09:26:41Z | - |
dc.description.version | Peer Reviewed | - |
dc.language.rfc3066 | eng | - |
dc.contributor.funder | Regione Autonoma della Sardegna | es_ES |
dc.contributor.funder | Ministerio de Economía y Competitividad (España) | es_ES |
dc.contributor.funder | Comunidad de Madrid | es_ES |
dc.relation.csic | Sí | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100003329 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/100012818 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100009873 | es_ES |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.openairetype | artículo | - |
item.cerifentitytype | Publications | - |
item.grantfulltext | open | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | With Fulltext | - |
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126319_postprint.pdf | Artículo principal | 1,65 MB | Adobe PDF | Visualizar/Abrir |
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