Enantio- and diastereocontrolled dopamine D1, D2, D3 and D4 receptor binding of N-(3-pyrrolidinylmethyl)benzamides synthesized from aspartic acid.
Subreceptor selectivity tuning of N-(3-pyrrolidinyl)benzamides leading to the selective dopamine D3 ligand ent1h and the derivatives 1g and 1e/ent1e which preferably recognize human D2 or D4 receptors, respectively, is described. Binding profiles were controlled by both, absolute and relative configuration. The enantiopure target compounds were synthesized from aspartic acid.
Thomas
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C
Institut für Pharmazie und Lebensmittelchemie, Universität Erlangen-Nürnberg, Erlangen, Germany.
Hübner
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Gmeiner
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D000818:Animals; D001224:Aspartic Acid / Q000031:analogs & derivatives*; D001549:Benzamides / Q000138:chemical synthesis / Q000494:pharmacology*; D002417:Cattle; D006801:Humans; D007700:Kinetics; D008956:Models, Chemical; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000494:pharmacology*; D011954:Receptors, Dopamine / Q000378:metabolism*
D001549:Benzamides; D011759:Pyrrolidines; D011954:Receptors, Dopamine; D001224:Aspartic Acid