title: Activity of N-(2-phenylethyl)-N-n-propyl-2-(3-hydroxyphenyl) ethylamine derivatives as dopamine receptor ligands.
abstract: The N-n-propyl-N-(2-phenylethyl)-2-(3-hydroxyphenyl)ethylamine (1, RU 24213) had been previously identified as selective agonist of DA D2 receptor subtype. In this paper we describe the synthesis and in vitro binding affinities of several derivatives of 1 substituted with fluorine, chlorine and methyl or hydroxy groups on the phenyl ring of the N-2-phenylethyl moiety. The results obtained indicate that these substitutions do not improve the D2 binding affinity. The introduction on the phenyl ring of two fluorine or chlorine atoms decreases with D1 affinity, and the dichloro derivatives are highly selective for the D2 receptor. Preliminary behavioural tests confirm that the dichloro derivatives behave as D2 selective agonists.
authors.affiliation: Department of Chemical Sciences, University of Camerino, MC, Italy.
authors.forename: F
authors.initials: F
authors.lastname: Claudi
authors.forename: M
authors.initials: M
authors.lastname: Cardellini
authors.forename: A
authors.initials: A
authors.lastname: Di Stefano
authors.forename: G
authors.initials: G
authors.lastname: Giorgioni
authors.forename: F
authors.initials: F
authors.lastname: Cantalamessa
authors.forename: F
authors.initials: F
authors.lastname: Renò
authors.forename: W
authors.initials: W
authors.lastname: Balduini
mesh_terms: D000818:Animals; D001552:Benzazepines / Q000494:pharmacology; D015259:Dopamine Agents / Q000494:pharmacology; D005021:Ethylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D008024:Ligands; D008787:Metoclopramide / Q000494:pharmacology; D009043:Motor Activity / Q000187:drug effects; D017072:Neostriatum / Q000187:drug effects / Q000378:metabolism; D010627:Phenethylamines / Q000494:pharmacology; D051381:Rats; D011954:Receptors, Dopamine / Q000187:drug effects*; D017447:Receptors, Dopamine D1 / Q000187:drug effects; D017448:Receptors, Dopamine D2 / Q000187:drug effects; D013134:Spiperone / Q000494:pharmacology; D013239:Stereotyped Behavior / Q000187:drug effects
chemical_list: D001552:Benzazepines; D015259:Dopamine Agents; D005021:Ethylamines; D008024:Ligands; D010627:Phenethylamines; D011954:Receptors, Dopamine; D017447:Receptors, Dopamine D1; D017448:Receptors, Dopamine D2; D013134:Spiperone; C016868:N-n-propyl-N-phenylethyl-4(3-hydroxyphenyl)ethylamine hydrochloride; D008787:Metoclopramide