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dc.contributor.authorRagusa, Giulioes_ES
dc.contributor.authorGómez-Cañas, Maríaes_ES
dc.contributor.authorMorales, Paulaes_ES
dc.contributor.authorHurst, D. P.es_ES
dc.contributor.authorDeligia, F.es_ES
dc.contributor.authorPazos, Ruthes_ES
dc.contributor.authorPinna, Gerard A.es_ES
dc.contributor.authorFernández-Ruiz, Javieres_ES
dc.contributor.authorGoya, Pilares_ES
dc.contributor.authorReggio, Patriciaes_ES
dc.contributor.authorJagerovic, Nadinees_ES
dc.contributor.authorGarcía-Arencibia, Moiséses_ES
dc.contributor.authorMurineddu, Gabrielees_ES
dc.date.issued2015-
dc.identifierdoi: 10.1016/j.ejmech.2015.06.057-
dc.identifierissn: 1768-3254-
dc.identifiere-issn: 1768-3254-
dc.identifier.citationEuropean Journal of Medicinal Chemistry 101: 651-667 (2015)es_ES
dc.identifier.urihttp://hdl.handle.net/10261/126319-
dc.description.abstractDuring 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.sponsorshipGM 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.publisherElsevieres_ES
dc.relationS2010/BMD-2308/CANNABes_ES
dc.relation.isversionofPostprintes_ES
dc.rightsopenAccesses_ES
dc.titleSynthesis, pharmacological evaluation and docking studies of pyrrole structure-based CB<inf>2</inf> receptor antagonistses_ES
dc.typeartículoes_ES
dc.identifier.doi10.1016/j.ejmech.2015.06.057-
dc.description.peerreviewedPeer reviewedes_ES
dc.relation.publisherversionhttp://dx.doi.org/10.1016/j.ejmech.2015.06.057es_ES
dc.date.updated2015-12-02T09:26:41Z-
dc.description.versionPeer Reviewed-
dc.language.rfc3066eng-
dc.contributor.funderRegione Autonoma della Sardegnaes_ES
dc.contributor.funderMinisterio de Economía y Competitividad (España)es_ES
dc.contributor.funderComunidad de Madrides_ES
dc.relation.csices_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100003329es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/100012818es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100009873es_ES
dc.type.coarhttp://purl.org/coar/resource_type/c_6501es_ES
item.openairetypeartículo-
item.cerifentitytypePublications-
item.grantfulltextopen-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.fulltextWith Fulltext-
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