Synthesis of simple analogues of methyllycaconitine -: an efficient method for the preparation of the N-substituted anthranilate pharmacophore

被引：21

作者：

Barker, D

Brimble, MA

McLeod, MD

机构：

[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand

[2] Univ Sydney, Sch Chem, Camperdown, NSW 2006, Australia

来源：

TETRAHEDRON | 2004年 / 60卷 / 28期

关键词：

methyllycaconitine; anthranilate esters; nicotinic acetylcholine receptors; alkaloids;

D O I：

10.1016/j.tet.2004.05.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several A and AE ring analogues of the alkaloid methyllycaconitine is reported. The key 2-(2"-methylsuccinimido)benzoate ester pharmacophore is introduced using an efficient two step procedure. Esterification of the alcohol precursors with N-(trifluoroacetyl)anthranilic acid under Steglich conditions followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate esters. Subsequent fusion with methylsuccinic anhydride affords the N-substituted anthranilate derivatives containing the key pharmacophore present in a range of commonly occurring Delphinium and Aconitum alkaloids. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：5953 / 5963

页数：11

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