New 2-thioether-substituted apomorphines as potent and selective dopamine D2 receptor agonists

Reet Reinart, Zsuzsanna Gyulai, Sándor Berényi, S. Antus, Argo Vonk, Ago Rinken, Attila Sipos

Research output: Article

5 Citations (Scopus)

Abstract

A set of novel apomorphine derivatives were synthesized with diversely functionalized side chains in the proximity of position 2 of the aporphine skeleton. Amino and/or carboxylic functions were introduced to this region of the backbone to test their pharmacological effects. During the synthesis of 2-(S-3-mercaptopropionic acid)-derivative a heteroring-fused congener was also isolated. The structural elucidation confirmed that the formation of this product was in accordance with our previous observations on the reaction of thebaine (2) with thiosalycilic acid. All the novel apomorphine congeners 4a-g were neuropharmacologically characterized to discover their dopaminergic profiles. Two derivatives were identified as D2 full agonists equipotent with apomorphine (1) having significantly increased D 2/D1 selectivity ratios.

Original languageEnglish
Pages (from-to)2992-2999
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume46
Issue number7
DOIs
Publication statusPublished - júl. 2011

Fingerprint

Dopamine D2 Receptors
Apomorphine
Dopamine Agonists
Sulfides
Derivatives
Thebaine
3-Mercaptopropionic Acid
Skeleton
Pharmacology
Acids

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology
  • Medicine(all)

Cite this

New 2-thioether-substituted apomorphines as potent and selective dopamine D2 receptor agonists. / Reinart, Reet; Gyulai, Zsuzsanna; Berényi, Sándor; Antus, S.; Vonk, Argo; Rinken, Ago; Sipos, Attila.

In: European Journal of Medicinal Chemistry, Vol. 46, No. 7, 07.2011, p. 2992-2999.

Research output: Article

Reinart, Reet ; Gyulai, Zsuzsanna ; Berényi, Sándor ; Antus, S. ; Vonk, Argo ; Rinken, Ago ; Sipos, Attila. / New 2-thioether-substituted apomorphines as potent and selective dopamine D2 receptor agonists. In: European Journal of Medicinal Chemistry. 2011 ; Vol. 46, No. 7. pp. 2992-2999.
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