Piperidinylpyrroles: design, synthesis and binding properties of novel and selective dopamine D4 receptor ligands.
Piperidinylpyrroles of type 3 were synthesized through a modified Paal-Knorr reaction. For the introduction of pyrrole-substituents high yielding transformations including Sonogashira cross-coupling reactions were utilized. Employment of the reagent TosMIC gave access to the regioisomeric oxazolyl derivatives 7 and 11 which showed the highest dopamine D4 receptor binding of the series investigated.
Haubmann
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Department of Medicinal Chemistry, Emil Fischer Center, Friedrich-Alexander University, Erlangen, Germany.
Hübner
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Gmeiner
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D000818:Animals; D001667:Binding, Competitive; D002417:Cattle; D018492:Dopamine Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology; D015195:Drug Design; D006801:Humans; D008024:Ligands; D015394:Molecular Structure; D011485:Protein Binding; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D017448:Receptors, Dopamine D2 / Q000378:metabolism*; D050638:Receptors, Dopamine D4; D013134:Spiperone / Q000378:metabolism
C493599:DRD4 protein, human; D018492:Dopamine Antagonists; D008024:Ligands; D011758:Pyrroles; D017448:Receptors, Dopamine D2; D050638:Receptors, Dopamine D4; D013134:Spiperone