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Synthesis and dopamine receptor binding affinity of 4H-thiochromenoapomorphines |
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| Authors: | Attila Sipos Miklós Tóth Franziska K U Mueller Jochen Lehmann Sándor Berényi | ||
| Institution: | 1. Department of Organic Chemistry, University of Debrecen, P.O. Box 20, 4010, Debrecen, Hungary 2. Institut für Pharmazie, Lehrstuhl für Pharmazeutische/Medizinische Chemie, Friedrich-Schiller-Universit?t Jena, Philosophenweg 14, 07743, Jena, Germany |
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| Abstract: | Abstract The synthesis of 4H-thiochromene derivatives of apomorphines, a novel class of isoquinoline alkaloid-related compounds, has been achieved by
different O-dealkylation methods applied on previously published heteroring-fused aporphinoids. Detailed DFT study has been presented
regarding the mechanism of the L-selectride-mediated multiple O-dealkylation of a seven-ring aporphine analogue. Dopamine-binding tests confirmed the essential function of 11-hydroxy moiety
of the aporphine skeleton and revealed a remarkable D1 over D2 specificity for the derivative having the 4H-thiochromene ring system attached to positions 2 and 3 of the aporphine backbone.
Graphical Abstract
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| Keywords: | Alkaloids Heterocycles Density functional calculations Molecular modeling Structure-activity relationships | ||
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