title: Synthesis and pharmacology of isoquinuclidine derivatives as 5-HT(3) ligands.
abstract: A series of 4-amino-5-chloro-2-methoxybenzoates and benzamides containing the 5- and 6-isoquinuclidinyl system was synthesised and evaluated for binding to 5-HT(3), 5-HT(4) and D(2) receptors. In general, the isoquinuclidine derivatives at the 5-position have shown to be more potent as 5-HT(3) ligands but they also possess 5-HT(4) and D(2) properties. However, the results show that the derivatives at the 6-position afforded the most promising compounds in terms of both receptor affinity and selectivity.
authors.affiliation: Departamento de Química Orgánica, Universidad de Alcalá, Ctra. Madrid-Barcelona Km. 33,600, 28871 Alcalá de Henares, Madrid, Spain. isabel.iriepa@uah.es
authors.forename: Isabel
authors.initials: I
authors.lastname: Iriepa
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Villasante
authors.forename: Enrique
authors.initials: E
authors.lastname: Gálvez
authors.forename: Luis
authors.initials: L
authors.lastname: Labeaga
authors.forename: Ana
authors.initials: A
authors.lastname: Innerarity
authors.forename: Aurelio
authors.initials: A
authors.lastname: Orjales
mesh_terms: D008024:Ligands; D011812:Quinuclidines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D011985:Receptors, Serotonin / Q000378:metabolism*; D044406:Receptors, Serotonin, 5-HT3; D013237:Stereoisomerism
chemical_list: D008024:Ligands; D011812:Quinuclidines; D011985:Receptors, Serotonin; D044406:Receptors, Serotonin, 5-HT3