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Synthesis and dopamine receptor binding of sulfur-containing aporphines.

Abstract：

:We investigated acid-catalyzed rearrangement of thebaine 14 and its N-propyl analog 15 with methanesulfonic acid in the presence of the nucleophiles methanethiol and hydrogen sulfide. R(-)-2-methylthioapocodeine 16, R(-)-2-methylthioapomorphine 18, and their N-n-propyl analogs 17, 19 were obtained by rearrangement in the presence of methanethiol. However, with hydrogen sulfide, rearrangement of thebaine 14 and its N-n-propyl analog 15 produced sulfide-linked bis-aporphines 21-24 instead of expected R(-)-2-mercaptoapocodeines 12, 13 and R(-)-2-mercaptoapomorphines 10, 11. R(-)-2-Methylthio-N-n-propylnorapomorphine 19 had higher affinity (Ki = 3.7 nM) at D2 receptors in rat forebrain tissue than other novel 2-substituted sulfur-containing aporphines (Ki > or = 50 nM). Behavioral testing of the novel agents in rat indicated moderate locomotor arousal after systemic injection, and none after intragastric administration, indicating poor oral bioavailability.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tóth M,Berényi S,Csutorás C,Kula NS,Zhang K,Baldessarini RJ,Neumeyer JL

doi

10.1016/j.bmc.2005.10.049

subject

Has Abstract

pub_date

2006-03-15 00:00:00

pages

1918-23

issue

6

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)01027-8

journal_volume

14

pub_type

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