title: Design, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases.
abstract: A series of phenylpiperazine-methyl-substituted 1H-pyrrolo[2,3-c]pyridine, imidazo[1,2-c]-, pyrrolo[2,3-d]- and pyrrolo[3,2-d]pyrimidines were prepared as selective dopamine D4-ligands. The pyrrolo[2,3-d]pyrimidine derivatives 12d (K(i)=1,9 nM) and 34 d (K(i)=2,4 nM) as well as the pyrrolo[3,2-d]pyrimidine Mannich base 49f (K(i)=2,8 nM) showed high dopamine D4 receptor activity superior to the atypical antipsychotic agent clozapine.
authors.affiliation: Department Chemie und Pharmazie, Lehrstuhl Pharmazeutische Chemie, Friedrich-Alexander-Universität, Erlangen, Germany.
authors.forename: Sabine
authors.initials: S
authors.lastname: Linz
authors.forename: Jörg
authors.initials: J
authors.lastname: Müller
authors.forename: Harald
authors.initials: H
authors.lastname: Hübner
authors.forename: Peter
authors.initials: P
authors.lastname: Gmeiner
authors.forename: Reinhard
authors.initials: R
authors.lastname: Troschütz
mesh_terms: D000818:Animals; D014150:Antipsychotic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D016466:CHO Cells; D002417:Cattle; D003024:Clozapine / Q000494:pharmacology; D006224:Cricetinae; D003412:Cricetulus; D006801:Humans; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011485:Protein Binding; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011954:Receptors, Dopamine / Q000378:metabolism; D050638:Receptors, Dopamine D4 / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D014150:Antipsychotic Agents; D010879:Piperazines; D011743:Pyrimidines; D011954:Receptors, Dopamine; D050638:Receptors, Dopamine D4; D003024:Clozapine; C031503:phenylpiperazine