ChemInform Abstract: New 2‐Thioether‐Substituted Apomorphines as Potent and Selective Dopamine D₂ Receptor Agonists.

Abstract

New 2-Thioether-Substituted Apomorphines as Potent and Selective Dopamine D 2 Receptor Agonists. -The introduction of substituents at position 2 of the aporphine backbone is suitable for the preparation of 2-O-and 2-S-substituted aporphines with the methanesulfonic acid-mediated rearrangement of thebaine (I). A set of apomorphine derivatives is synthesized with diversely functionalized side chains in the proximity of position 2 of the aporphine skeleton. During the synthesis of mercaptopropionic acid derivative (VIII) the heteroring-fused congener (IX) is formed as well. Two apomorphine congeners, (IVb) and (VI), are identified as D2 full agonists, equipotent to apomorphine, but exhibiting significantly increased D2/D1 selectivity ratios. -(REINART, R.; GYULAI, Z.; BERENYI, S.; ANTUS, S.; VONK, A.; RINKEN, A.; SIPOS*, A.; Eur.