Synthesis of (-)-5,8-dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene:: An inhibitor of β-amyloid1-42 aggregation

被引：24

作者：

Parker, MH ^{[1
]}

Chen, R ^{[1
]}

Conway, KA ^{[1
]}

Lee, DHS ^{[1
]}

Luo, C ^{[1
]}

Boyd, RE ^{[1
]}

Nortey, SO ^{[1
]}

Ross, TM ^{[1
]}

Scott, MK ^{[1
]}

Reitz, AB ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev, Drug Discovery Div, Spring House, PA 19477 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2002年 / 10卷 / 11期

关键词：

D O I：

10.1016/S0968-0896(02)00251-1

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：

A concise synthesis of the beta-amyloid(1-42) aggregation inhibitor (-)-5,8-dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene [(-)-2] has been developed. The key step is a regio- and diastereoselective hydroboration-amination sequence to convert alkene 6 into amine 9. Enantiomeric resolution was achieved by recrystallization of amine 9 as the dibenzoyl-D-tartaric acid salt. Hydroquinone 2 is a potent inhibitor of the fibrillar aggregation of beta-amyloid as determined in two different assay systems. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3565 / 3569

页数：5

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