Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors.
The asymmetric synthesis of chiral piperazinylpropylisoxazoline analogues, (R)-(+)-1, 2 and (S)-(-)-1, 2 was accomplished through a seven-step sequence of reactions, which involved asymmetric 1,3-dipolar cycloaddition, alkyl chain extension, and reductive amination as key reactions. Chiral ligands (R)-(+)-1, 2 exhibited the higher binding affinity and selectivity for the D(3) receptor over the D(4) receptor than (S)-(-)-1, 2 ligands.
Jung
Ji Young
JY
Department of Chemistry and Institute of Basic Science, Sungshin Women's University, Seoul 136-742, South Korea.
Jung
Sun Ho
SH
Koh
Hun Yeong
HY
D018492:Dopamine Antagonists / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D008958:Models, Molecular; D011485:Protein Binding; D011954:Receptors, Dopamine / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship
D018492:Dopamine Antagonists; D007555:Isoxazoles; D011954:Receptors, Dopamine