title: Dopaminergic 7-aminotetrahydroindolizines: ex-chiral pool synthesis and preferential D3 receptor binding.
abstract: Starting from both isomers of enantiopure asparagine, heterocyclic bioisosteres of the preferential dopamine D3 receptor agonist (R)-7-OH-DPAT were investigated when SAR studies led to the 3-formyl substituted aminoindolizine (S)-1e (FAUC 54) displaying a K(i) value of 6.0 nM for the high affinity D3 binding site. In contrast, D3 affinity of the enantiomer (R)-1e was 300 fold lower.
authors.affiliation: Department of Medicinal Chemistry, Emil Fischer Center, Friedrich-Alexander University, Schuhstrasse 19, D-91052 Erlangen, Germany.
authors.forename: T
authors.initials: T
authors.lastname: Lehmann
authors.forename: H
authors.initials: H
authors.lastname: Hübner
authors.forename: P
authors.initials: P
authors.lastname: Gmeiner
mesh_terms: D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D007212:Indolizines / Q000138:chemical synthesis* / Q000378:metabolism*; D017448:Receptors, Dopamine D2 / Q000378:metabolism*; D050637:Receptors, Dopamine D3
chemical_list: D007212:Indolizines; D017448:Receptors, Dopamine D2; D050637:Receptors, Dopamine D3; C035094:indolizine