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

共 50 条

[41] AZIRIDINES FROM BETA-IODOCARBAMATES - 1,2,3,4-TETRAHYDRONAPHTHALENE(1,2)IMINE
HEATHCOCK, CH
HASSNER, A
ORGANIC SYNTHESES, 1988, 50-9 : 967 - 968
[42] SYNTHESIS AND ISOMERIZATION OF 1,4-EPOXY-2,3-DIBROMOMETHYLENE-1,2,3,4-TETRAHYDRONAPHTHALENE
WITTIG, G
REUTHER, W
ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1972, 765 (NOV): : 47 - 54
[43] THERMAL REACTIONS OF 1,4-BRIDGED-1,2,3,4-TETRAHYDRONAPHTHALENE DERIVATIVES
HEANEY, H
PRICE, AP
SHARMA, RP
LEY, SV
TETRAHEDRON LETTERS, 1972, (30) : 3067 - &
[44] MOLECULAR-STRUCTURE OF ANTI-3,4-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE 1,2-OXIDE
KLEIN, CL
STEVENS, ED
CANCER RESEARCH, 1984, 44 (04) : 1523 - 1526
[45] REACTION OF DIMETHYLOXOSULFONIUM METHYLIDE WITH AROMATIC METHOXYLATED 1,2,3,4-TETRAHYDRONAPHTHALENE 1-ONES
CROOKS, PA
SOMMERVILLE, R
CHEMISTRY & INDUSTRY, 1984, (09) : 350 - 351
[46] ASYMMETRIC-SYNTHESIS OF R-(-)-2-ACETYL-2-HYDROXY-5-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALENE - A KEY SYNTHON FOR SYNTHESIS OF 11-DEOXYANTHRACYCLINONES
RAO, AVR
CHANDA, B
BORATE, HB
GUPTA, M
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (01): : 9 - 11
[47] Synthesis and biological activities of 1-keto-3-carboxy-6,7-methylenedioxy-1,2,3,4-tetrahydronaphthalene derivatives
Prabhu, PJ
Bhise, NB
Dave, MA
ASIAN JOURNAL OF CHEMISTRY, 2003, 15 (02) : 639 - 644
[48] Investigation of Fickian diffusion in the ternary mixture of 1,2,3,4-tetrahydronaphthalene, isobutylbenzene, and dodecane
Mialdun, A.
Sechenyh, V.
Legros, J. C.
Ortiz de Zarate, J. M.
Shevtsova, V.
JOURNAL OF CHEMICAL PHYSICS, 2013, 139 (10):
[49] MASS SPECTRA OF SOME LIGNANS OF 1-PHENYL-1,2,3,4-TETRAHYDRONAPHTHALENE SERIES
PELTER, A
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (01): : 74 - &
[50] CRYSTAL AND MOLECULAR-STRUCTURE OF TRANS-1-BENZYLIDENE-1,2,3,4-TETRAHYDRONAPHTHALENE
BUKOWSKASTRZYZEWSKA, M
SKOWERANDA, J
JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1987, 17 (05): : 625 - 631

← 1 2 3 4 5 →