Gmeiner P, Hübner H (2003)
Publication Type: Journal article
Publication year: 2003
Publisher: Elsevier
Book Volume: 14
Pages Range: 3153-3172
DOI: 10.1016/j.tetasy.2003.08.020
Starting from natural 4-hydroxyproline, an ex-chiral pool approach is described giving access to 2-aminoalkylpyrrolidine derivatives that were used as chiral building blocks for the synthesis of bioactive 2-methoxybenzamide derivatives. The 4-hydroxy substituent can be displaced employing organocuprates as useful carbanion equivalents. Dopamine and serotonin binding studies involving the subtypes D1, D2long, D2short, D3 and D4 as well as 5-HT1A and 5-HT2, respectively, provided interesting insights into stereoselective structure activity relationships. The (2S,4R)-2-aminomethylpyrrolidine derivative ent-66 and the (2R,4S)-2- aminoethylpyrrolidine derivative 68 showed remarkable affinity and preference for the dopamine D3 and D4 receptor subtypes, respectively, both being putatively associated to the symptoms of schizophrenia. © 2003 Elsevier Ltd. All rights reserved.
APA:
Gmeiner, P., & Hübner, H. (2003). Enantiospecific synthesis and receptor binding of novel dopamine receptor ligands employing natural 4-hydroxyproline as a practical and flexible building block. Tetrahedron-Asymmetry, 14, 3153-3172. https://doi.org/10.1016/j.tetasy.2003.08.020
MLA:
Gmeiner, Peter, and Harald Hübner. "Enantiospecific synthesis and receptor binding of novel dopamine receptor ligands employing natural 4-hydroxyproline as a practical and flexible building block." Tetrahedron-Asymmetry 14 (2003): 3153-3172.
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