Preparation of dopaminergic N-alkyl-benzyltetrahydroisoquinolines using a 'one-pot' procedure in acid medium

被引：23

作者：

Andreu, I

Cortes, D ^{[1
]}

Protais, P

Cassels, BK

Chagraoui, A

Cabedo, N

机构：

[1] Univ Valencia, Fac Farm, Dept Farmacol Farmacognosia & Farmacodinamia, Valencia 46100, Spain

[2] Univ Rouen, Fac Med Pharm, Physiol Lab, F-76183 Rouen, France

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 05期

关键词：

D O I：

10.1016/S0968-0896(00)00027-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 D-2 dopamine receptors, while its N-methylated homologue (8) displays higher affinities for both D-1 and D-2 receptor types, with an unexpected increase in D1 dopamine receptor affinity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：889 / 895

页数：7

共 14 条

[1]

BERMEJO A, 1995, NAT PROD LETT, V6, P57, DOI DOI 10.1080/10575639508044088.

[2] Synthesis and dopamine receptor selectivity of the benzyltetrahydroisoquinoline, (R)-(+)-nor-roefractine [J].