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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页码：5953 / 5963
页数：11
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