6533b824fe1ef96bd127ffd8

RESEARCH PRODUCT

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

Almudena BermejoRicardo D. EnrizRicardo D. EnrizSebastian A. AndujarSebastian A. AndujarVanessa RomeroNoureddine El AouadDiego CortesM. Dolores IvorraNuria CabedoFernando D. SuvireAngel SerranoPaloma MarínInmaculada Berenguer

subject

inorganic chemicalsHalogenationStereochemistryChemical synthesisReceptors DopamineStructure-Activity Relationshipchemistry.chemical_compoundStructure–activity relationshipsDopamineTetrahydroisoquinolinesBiogenic amineDrug DiscoverymedicineAnimalsStructure–activity relationshipRats WistarNeurotransmitterDopamine receptorsSTRUCTURE-ACTIVITY RELATIONSHIPSPharmacologychemistry.chemical_classification1-Halogenated benzyl-7-chloro-6-hydroxy-tetrahydroisoquinolinesDopamine uptakReceptors Dopamine D2Receptors Dopamine D1Otras Ciencias QuímicasOrganic ChemistryDopaminergicCiencias QuímicasGeneral MedicineBinding1-Halogenated benzyl-7-chloro-6-hydroxytetrahydroisoquinolinesRatschemistryDopamine receptorDOPAMINE UPTAKECatecholamineFemaleCIENCIAS NATURALES Y EXACTASProtein Bindingmedicine.drug

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 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. (C) 2009 Elsevier Masson SAS. All rights reserved.

yearjournalcountryeditionlanguage
2009-11-01
10.1016/j.ejmech.2009.06.033https://doi.org/10.1016/j.ejmech.2009.06.033