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Title:
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Preparation of Dopaminergic N-Alkyl-benzyltetrahydro-isoquinolines Using a `One-Pot' Procedure in Acid Medium |
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Author:
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Andreu, Inmaculada; Cortes, Diego; Protais, Philippe; Cassels, Bruce K.; Chagraoui, Abdeslam; Cabedo, Nuria
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Abstract:
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AbstractÐThe preparation of N-methyl-BTHIQ (4) from N-phenylethyl-phenacetamide (1) by cyclization, reduction and N-alkyl-
ation in acid medium has been achieved in good yield in a `one-pot' procedure. Acylation of imine (2) intermediate a orded 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 a nities for both D1 and D2 receptor types, with an unexpected increase in D1
dopamine receptor a nity. |
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URI:
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http://www.captura.uchile.cl/handle/2250/16452
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Date:
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1999-11-15 |
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dc.identifier.citation:
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Bioorganic & Medicinal Chemistry 8: 889-895, 2000. |