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dc.contributor.authorLucena-Serrano, Cristina
dc.contributor.authorLucena-Serrano, Ana
dc.contributor.authorRivera-Ramírez, Alicia 
dc.contributor.authorLópez-Romero, Juan Manuel 
dc.contributor.authorValpuesta-Fernández, María 
dc.contributor.authorDíaz-Morilla, Amelia 
dc.date.accessioned2024-01-26T12:58:24Z
dc.date.available2024-01-26T12:58:24Z
dc.date.created2024
dc.date.issued2018-07-05
dc.identifier.citationLucena-Serrano, C., Lucena-Serrano, A., Rivera, A., López-Romero, J. M., Valpuesta, M., & Díaz, A. (2018). Synthesis and dopaminergic activity of a series of new 1-aryl tetrahydroisoquinolines and 2-substituted 1-aryl-3-tetrahydrobenzazepines. Bioorganic Chemistry, 80, 480–491es_ES
dc.identifier.urihttps://hdl.handle.net/10630/29331
dc.description.abstractA series of new 1-aryl-6,7-dihydroxy tetrahydroisoquinolines with several substitution patterns in the 1-aryl group at C-1 were prepared in good yields. The influence of each substituent on the affinity and selectivity for D1 and D2 dopaminergic receptors was studied. Moreover, N-alkyl salts of these tetrahydroisoquinolines were used as starting material to synthesize a series of new 1-aryl-7,8-dihydroxy 3-tetrahydrobenzazepines derivatives with electron-withdrawing substituents at C-2 position by the diastereoselective Stevens rearrangement. The structure-activity relationship of these compounds was explored to evaluate the effect of the functional group at C-2 in benzazepines and the modification in the aryl group at the isoquinoline C-1 position towards the affinity and selectivity for the mentioned receptors. The 1-aryl-6,7-dihydroxy tetrahydroisoquinoline 4c shows significant affinity towards D2 receptor, with Ki value of 31 nM. This significant affinity can be attributed to the presence of a thiomethyl group, and it is the most active 1-aryl-6,7-dihydroxy tetrahydroisoquinoline derivative reported to date.es_ES
dc.description.sponsorshipThis research was supported by the Spanish “Ministerio de Economía, Industria y Competividad” Project CTQ 2016-76311-P.es_ES
dc.language.isoenges_ES
dc.publisherElsevieres_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectDopamina - Receptoreses_ES
dc.subjectQuímica biorgánicaes_ES
dc.subject.otherTetrahydroisoquinolineses_ES
dc.subject.other3-tetrahydrobenzazepineses_ES
dc.subject.otherStevens rearrangementes_ES
dc.subject.otherDopamine receptorses_ES
dc.subject.otherBindinges_ES
dc.titleSynthesis and dopaminergic activity of a series of new 1-aryl tetrahydroisoquinolines and 2-substituted 1-aryl-3-tetrahydrobenzazepines.es_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.identifier.doi10.1016/j.bioorg.2018.06.038
dc.rights.ccAttribution-NonCommercial-NoDerivatives 4.0 Internacional
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersiones_ES


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