title: Structure-activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives.
abstract: 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 D(1)-like and/or D(2)-like dopamine receptors in striatal membranes, although they were unable to inhibit [(3)H]-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 K(i) 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.
authors.affiliation: Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot, Valencia, Spain.
authors.forename: Noureddine
authors.initials: N
authors.lastname: El Aouad
authors.forename: Inmaculada
authors.initials: I
authors.lastname: Berenguer
authors.forename: Vanessa
authors.initials: V
authors.lastname: Romero
authors.forename: Paloma
authors.initials: P
authors.lastname: Marín
authors.forename: Angel
authors.initials: A
authors.lastname: Serrano
authors.forename: Sebastián
authors.initials: S
authors.lastname: Andujar
authors.forename: Fernando
authors.initials: F
authors.lastname: Suvire
authors.forename: Almudena
authors.initials: A
authors.lastname: Bermejo
authors.forename: M Dolores
authors.initials: MD
authors.lastname: Ivorra
authors.forename: Ricardo D
authors.initials: RD
authors.lastname: Enriz
authors.forename: Nuria
authors.initials: N
authors.lastname: Cabedo
authors.forename: Diego
authors.initials: D
authors.lastname: Cortes
mesh_terms: D000818:Animals; D005260:Female; D054879:Halogenation; D011485:Protein Binding; D051381:Rats; D017208:Rats, Wistar; D011954:Receptors, Dopamine / Q000378:metabolism*; D017447:Receptors, Dopamine D1 / Q000378:metabolism; D017448:Receptors, Dopamine D2 / Q000378:metabolism; D013329:Structure-Activity Relationship; D044005:Tetrahydroisoquinolines / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D011954:Receptors, Dopamine; D017447:Receptors, Dopamine D1; D017448:Receptors, Dopamine D2; D044005:Tetrahydroisoquinolines