Synthesis and neuropharmacological evaluation of new (R)-(-) and (S)-(+)-2-(alkylthio)aporphine derivatives

Sándor Berényi, Csaba Csutorás, Sándor Makleit, Ferenc Auth, István Laszlovszky, Béla Kiss, Egon Kárpáti, Miklós Löw

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14 Citations (Scopus)

Abstract

In the presence of thiols, the methanesulfonic acid-catalyzed rearrangement of thebaine (7), or N-(n-propyl)northebaine (8) is accompanied by nucleophilic substitution and O-demethylation to furnish the corresponding 2-(alkylthio)aporphines (9, 10, 11, 12). Actions of these derivatives on the dopaminergic system are similar to apomorphine and N-(n-propyl)-norapomorphine, except the S-enantiomer ((S)-9) which was much less active.

Original languageEnglish
Pages (from-to)509-518
Number of pages10
JournalMedicinal Chemistry Research
Volume7
Issue number9
Publication statusPublished - Dec 1 1997

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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    Berényi, S., Csutorás, C., Makleit, S., Auth, F., Laszlovszky, I., Kiss, B., Kárpáti, E., & Löw, M. (1997). Synthesis and neuropharmacological evaluation of new (R)-(-) and (S)-(+)-2-(alkylthio)aporphine derivatives. Medicinal Chemistry Research, 7(9), 509-518.