6533b831fe1ef96bd1298e4f
RESEARCH PRODUCT
Preparation of dopaminergic N-alkyl-benzyltetrahydroisoquinolines using a 'one-pot' procedure in acid medium.
Philippe ProtaisImmaculada AndreuNuria CabedoBruce K. CasselsDiego CortesAbdeslam Chagraouisubject
Bicyclic moleculeStereochemistryReceptors Dopamine D2Receptors Dopamine D1Spectrum AnalysisOrganic ChemistryClinical BiochemistryDopaminergicImineDopamine AgentsPharmaceutical ScienceIsoquinolinesBiochemistryChemical synthesisAcylationchemistry.chemical_compoundchemistryDopamine receptor D2Drug DiscoveryMolecular MedicineStereoselectivitySelectivityMolecular Biologydescription
The preparation of N-methyl-BTHIQ (4) from N-phenylethyl-phenacetamide (1) by cyclization, reduction and N-alkylation in acid medium has been achieved in good yield in a 'one-pot' procedure. Acylation of imine (2) intermediate afforded the Z and E stereoselectivity in the enamide formation. 6-Hydroxy-BTHIQ (7) shows selectivity for D2 dopamine receptors, while its N-methylated homologue (8) displays higher affinities for both D1 and D2 receptor types, with an unexpected increase in D1 dopamine receptor affinity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2000-07-06 |