SYNTHESIS AND NEUROPHARMACOLOGICAL EVALUATION OF NEW (R)-(-)-2-(ALKYLTHIO)APORPHINE AND (S)-(-2-(ALKYLTHIO)APORPHINE DERIVATIVES())

Authors
BERENYI S CSUTORAS C MAKLEIT S AUTH F LASZLOVSZKY I KISS B KARPATI E LOW M
Citation
S. Berenyi et al., SYNTHESIS AND NEUROPHARMACOLOGICAL EVALUATION OF NEW (R)-(-)-2-(ALKYLTHIO)APORPHINE AND (S)-(-2-(ALKYLTHIO)APORPHINE DERIVATIVES()), Medicinal chemistry research, 7(9), 1997, pp. 509-518
Citations number
22
Journal title
Medicinal chemistry research → ACNP
ISSN journal
10542523
Volume
7
Issue
9
Year of publication
1997
Pages
509 - 518
Database
ISI
SICI code
1054-2523(1997)7:9<509:SANEON>2.0.ZU;2-L
Abstract
In the presence of thiols, the methanesulfonic acid-catalyzed rearrang ement of thebaine (7), or N-(n-propyl)northebaine (8) is accompanied b y nucleophilic substitution and O-demethylation to furnish the corresp onding 2-(alkylthio)aporphines (9, 1O, 11, 12). Actions of these deriv atives on the dopaminergic system are similar to apomorphine and N-(n- propyl)-norapomorphine, except the S-enantiomer ((S)-9) which was much less active.