Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives

Two series of halogenated 1-benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines were prepared to explore the influence of each series on the affinity for dopamine receptors. All the compounds displayed a high affinity for D1-like and/or D2-like dopamine receptors in striatal membranes, although they w...

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Detalles Bibliográficos
Autores: El Aouad, Noureddine, Berenguer, Inmaculada, Romero, Vanessa, Marín, Paloma, Serrano, Ángel, Andujar, Sebastian Antonio, Suvire, Fernando Daniel, Bermejo, Almudena, Ivorra, M. Dolores, Enriz, Ricardo Daniel, Cabedo, Nuria, Cortes, Diego
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2009
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/113647
Acceso en línea:http://hdl.handle.net/11336/113647
Access Level:acceso abierto
Palabra clave:1-Halogenated benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines
BINDING
DOPAMINE RECEPTORS
DOPAMINE UPTAKE
STRUCTURE-ACTIVITY RELATIONSHIPS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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oai_identifier_str oai:ri.conicet.gov.ar:11336/113647
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spelling Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivativesEl Aouad, NoureddineBerenguer, InmaculadaRomero, VanessaMarín, PalomaSerrano, ÁngelAndujar, Sebastian AntonioSuvire, Fernando DanielBermejo, AlmudenaIvorra, M. DoloresEnriz, Ricardo DanielCabedo, NuriaCortes, Diego1-Halogenated benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolinesBINDINGDOPAMINE RECEPTORSDOPAMINE UPTAKESTRUCTURE-ACTIVITY RELATIONSHIPShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two series of halogenated 1-benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines were prepared to explore the influence of each series on the affinity for dopamine receptors. All the compounds displayed a high affinity for D1-like and/or D2-like dopamine receptors in striatal membranes, although they were unable to inhibit [3H]-dopamine uptake in striatal synaptosomes. The halogen placed on the benzylic ring in 1-benzyl-THIQs, compounds of the series 1, 2′-bromobenzyl derivatives with Ki values into the nanomolar range, and the series 2, 2′,4′-dichlorobenzyl-THIQ homologues, proves to be an important factor to modulate affinity at dopamine receptor.Fil: El Aouad, Noureddine. Universidad de Valencia; EspañaFil: Berenguer, Inmaculada. Universidad de Valencia; EspañaFil: Romero, Vanessa. Universidad de Valencia; EspañaFil: Marín, Paloma. Universidad de Valencia; EspañaFil: Serrano, Ángel. Universidad de Valencia; EspañaFil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Bermejo, Almudena. Universidad Politécnica de Valencia; España. Universidad de Valencia; EspañaFil: Ivorra, M. Dolores. Universidad de Valencia; EspañaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Cabedo, Nuria. Universidad de Valencia; España. Universidad Politécnica de Valencia; EspañaFil: Cortes, Diego. Universidad de Valencia; EspañaElsevier France-editions Scientifiques Medicales Elsevier2009-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/113647El Aouad, Noureddine; Berenguer, Inmaculada; Romero, Vanessa; Marín, Paloma; Serrano, Ángel; et al.; Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 44; 11; 11-2009; 4616-46210223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0223523409003572info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2009.06.033info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:42:12Zoai:ri.conicet.gov.ar:11336/113647instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982024-05-08 13:42:13.117CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
title Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
spellingShingle Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
El Aouad, Noureddine
1-Halogenated benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines
BINDING
DOPAMINE RECEPTORS
DOPAMINE UPTAKE
STRUCTURE-ACTIVITY RELATIONSHIPS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
title_full Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
title_fullStr Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
title_full_unstemmed Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
title_sort Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives
dc.creator.none.fl_str_mv El Aouad, Noureddine
Berenguer, Inmaculada
Romero, Vanessa
Marín, Paloma
Serrano, Ángel
Andujar, Sebastian Antonio
Suvire, Fernando Daniel
Bermejo, Almudena
Ivorra, M. Dolores
Enriz, Ricardo Daniel
Cabedo, Nuria
Cortes, Diego
author El Aouad, Noureddine
author_facet El Aouad, Noureddine
Berenguer, Inmaculada
Romero, Vanessa
Marín, Paloma
Serrano, Ángel
Andujar, Sebastian Antonio
Suvire, Fernando Daniel
Bermejo, Almudena
Ivorra, M. Dolores
Enriz, Ricardo Daniel
Cabedo, Nuria
Cortes, Diego
author_role author
author2 Berenguer, Inmaculada
Romero, Vanessa
Marín, Paloma
Serrano, Ángel
Andujar, Sebastian Antonio
Suvire, Fernando Daniel
Bermejo, Almudena
Ivorra, M. Dolores
Enriz, Ricardo Daniel
Cabedo, Nuria
Cortes, Diego
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 1-Halogenated benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines
BINDING
DOPAMINE RECEPTORS
DOPAMINE UPTAKE
STRUCTURE-ACTIVITY RELATIONSHIPS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic 1-Halogenated benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines
BINDING
DOPAMINE RECEPTORS
DOPAMINE UPTAKE
STRUCTURE-ACTIVITY RELATIONSHIPS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description Two series of halogenated 1-benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolines were prepared to explore the influence of each series on the affinity for dopamine receptors. All the compounds displayed a high affinity for D1-like and/or D2-like dopamine receptors in striatal membranes, although they were unable to inhibit [3H]-dopamine uptake in striatal synaptosomes. The halogen placed on the benzylic ring in 1-benzyl-THIQs, compounds of the series 1, 2′-bromobenzyl derivatives with Ki values into the nanomolar range, and the series 2, 2′,4′-dichlorobenzyl-THIQ homologues, proves to be an important factor to modulate affinity at dopamine receptor.
publishDate 2009
dc.date.none.fl_str_mv 2009-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/113647
El Aouad, Noureddine; Berenguer, Inmaculada; Romero, Vanessa; Marín, Paloma; Serrano, Ángel; et al.; Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 44; 11; 11-2009; 4616-4621
0223-5234
CONICET Digital
CONICET
url http://hdl.handle.net/11336/113647
identifier_str_mv El Aouad, Noureddine; Berenguer, Inmaculada; Romero, Vanessa; Marín, Paloma; Serrano, Ángel; et al.; Structure–activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 44; 11; 11-2009; 4616-4621
0223-5234
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0223523409003572
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2009.06.033
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier France-editions Scientifiques Medicales Elsevier
publisher.none.fl_str_mv Elsevier France-editions Scientifiques Medicales Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 15,812455

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