title: [Selective dopamine D-2 autoreceptor agonists with 8-azaindole substructure: synthesis and theoretical studies].
abstract: Starting from the 1,3-dipolar cycloaddition product 6a the peri-fused beta-ketoester 7 is prepared. 7 is employed as a key intermediate for the synthesis of the D-2 autoreceptor agonist 5. Two alternative approaches are used for installing the amino function: electrophilic amination and Curtius rearrangement. The distribution of charge of the aromatic moiety of 5 has been determined by molecular orbital calculations and compared to the respective values of the ergolines. The results of ab-initio calculations and semi-empirical methods have been compared.
authors.affiliation: Institut für Pharmazie und Lebensmittelchemie, Ludwig-Maximilians-Universität, München.
authors.forename: P
authors.initials: P
authors.lastname: Gmeiner
authors.forename: J
authors.initials: J
authors.lastname: Sommer
mesh_terms: D003198:Computer Simulation; D015259:Dopamine Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D017448:Receptors, Dopamine D2 / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D015259:Dopamine Agents; D007211:Indoles; D017448:Receptors, Dopamine D2
vernacular_title: Selektive Dopamin D-2 Autorezeptor Agonisten mit 8-Azaindol Substruktur: Synthese und theoretische Untersuchungen.