title: Novel selective kappa-opioid ligands.
abstract: The single-crystal X-ray structures of (-)-dimethyl[(2S)-1-(5,6,7,8- tetrahydro-5-oxonaphthalene-2-acetyl)piperidin-2-ylmethyl ]ammonium chloride, C20H29N2O2+.Cl-(BRL-53001A), and (-)-ethylmethyl[(2S)-1-(5,6,7,8-tetrahydro-5-oxonaphthalene- 2- acetyl)piperidin-2-ylmethyl]-ammonium chloride dihydrate, C21H31N2O2+.Cl-.2H2O (BRL-53188A), have been determined. The two molecules have different conformations in the 1-tetralon-6-ylacetyl residue but the same conformation in the 1-acetyl-2-(dialkylaminomethyl)piperidine moiety. The conformations found are in agreement with the required chemical features for kappa affinity and antinociceptive potency.
authors.affiliation: Laboratorium voor Analytische Chemie en Medicinale Fysicochemie, Faculteit Farmaceutische Wetenschappen, Katholieke Universiteit Leuven, Belgium. maurice.peeters@farm.kuleuven.ac.be
authors.forename: O M
authors.initials: OM
authors.lastname: Peeters
authors.forename: D
authors.initials: D
authors.lastname: Jamroz
authors.forename: N M
authors.initials: NM
authors.lastname: Blaton
authors.forename: C J
authors.initials: CJ
authors.lastname: De Ranter
mesh_terms: D018360:Crystallography, X-Ray; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D010880:Piperidines / Q000737:chemistry*; D017473:Receptors, Opioid, kappa / Q000819:agonists*; D013764:Tetrahydronaphthalenes / Q000737:chemistry*
chemical_list: C119045:BRL 53001A; C119046:BRL 53188A; D008024:Ligands; D010880:Piperidines; D017473:Receptors, Opioid, kappa; D013764:Tetrahydronaphthalenes