Conformational study of N-alkyl-benzyltetrahydroisoquinolines alkaloid

被引：8

作者：

Suvire, FD

Andreu, I

Bermejo, A

Zamora, MA

Cortes, D

Enriz, RD

机构：

[1] Univ Nacl San Luis, Dept Quim, RA-5700 San Luis, Argentina

[2] Univ Valencia, Fac Farm, Dept Farmacol Farmacognosia & Farmacodinam, Valencia 46100, Spain

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2003年 / 666卷

关键词：

conformation; ab initio and DFT calculations; benzyltetrahydroisoquinolines; dopamine D-1-receptor;

D O I：

10.1016/j.theochem.2003.08.019

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An exhaustive conformational study on the benzyltetrahydroisoquinolines (BTHIQ) from ab initio (RHF/6-31G(d)) calculations was carried out. The effects of different substituents at chiral C-1 atom were also considered. Our results indicate that different substituents at C-1 in BTHIQ molecules introduce a significant steric hindrance which, in turn, might be responsible for a conformational restriction favouring or disfavouring the spatial orientation of the lone pairs of N atom allowing or not the electronic attachment with the side chain of Asp residue. These results can serve as an aid for designing suitable structures of BTHIQs for better dopamine D-1-receptor inhibitory activity. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：109 / 116

页数：8

共 15 条

[1] NNC-112, NNC-687 AND NNC-756, NEW SELECTIVE AND HIGHLY POTENT DOPAMINE D1 RECEPTOR ANTAGONISTS [J].