Synthesis of diastereomieric 13-amido-substituted huprines as potential high affinity acetylcholinesterase inhibitors

被引：19
作者：
Camps, P
Gómez, E
Muñoz-Torrero, D
Font-Bardia, M
Solans, X
机构：
[1] Univ Barcelona, Fac Farm, CSIC, Unitat Associada Lab Quim Farmacuet, E-08028 Barcelona, Spain
[2] Univ Barcelona, Fac Geol, Dept Cristal Iografia & Diposits Minerals, E-08028 Barcelona, Spain
来源：
TETRAHEDRON | 2003年 / 59卷 / 23期
关键词：
acetylcholinesterase inhibitors; methanesulfonamido derivatives; huprines;
D O I：
10.1016/S0040-4020(03)00577-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two diastereomeric huprines additionally functionalized at position 13 with a methanesulfonamido group have been synthesized in seven steps from the known 9,9-ethylenedioxybicyclo[3.3.1]nonane-3,7-dione (5). In a key-step, nickel boride non-stereoselective reduction of an oxime gave a mixture of amines which was separated as methanesulfonamido derivatives. The substitution pattern of these huprines could lead to an extended binding near the active site of acetylcholinesterase (AChE), and consequently to improved AChE inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.
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收藏
页码：4143 / 4151
页数：9
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