Synthesis and glycosidase inhibitory activity of enantiopure polyhydroxylated octahydroindoles and decahydroquinolines, analogs to castanospermine

被引:22
作者
Gravier-Pelletier, C [1 ]
Maton, W [1 ]
Bertho, G [1 ]
Le Merrer, Y [1 ]
机构
[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, CNRS, UMR 8601, F-75270 Paris 06, France
关键词
alkaloid; azasaccharide; bicyclic compounds; castanospermine; glycosidase; octahydroindole; decahydroquinoline; reductive amination;
D O I
10.1016/j.tet.2003.09.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of new enantiopure polyhydroxylated octahydroindoles and decahydroquinolines, analogs to castanospermine, via a double reductive amination of enantiopure cyclic ketoaldehyde, and their inhibitory activity against alpha- or beta-D-glucosidases, alpha-D-mannosidase and alpha-L-fucosidase are described. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8721 / 8730
页数:10
相关论文
共 27 条
[1]   Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems. Part III: Novel 2-alkly substituents containing cationic heteroaromatics linked via a C-N bond [J].
Azami, H ;
Barrett, D ;
Matsuda, K ;
Tsutsumi, H ;
Washizuka, K ;
Sakurai, M ;
Kuroda, S ;
Shirai, F ;
Chiba, T ;
Kamimura, T ;
Murata, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) :1665-1682
[2]   EXPEDITIOUS SYNTHESIS OF AZASUGARS BY THE DOUBLE REDUCTIVE AMINATION OF DICARBONYL SUGARS [J].
BAXTER, EW ;
REITZ, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3175-3185
[3]   Application of the tandem Stryker reduction-aldol cyclization strategy to the asymmetric synthesis of lucinone [J].
Chiu, P ;
Szeto, CP ;
Geng, Z ;
Cheng, KF .
TETRAHEDRON LETTERS, 2001, 42 (24) :4091-4093
[4]   OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].
COREY, EJ ;
ERICKSON, BW .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&
[5]   An ascending synthesis of adrenalcorticosteroids. The total synthesis of (+)-adrenosterone [J].
Dzierba, CD ;
Zandi, KS ;
Mollers, T ;
Shea, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (19) :4711-4712
[6]   An efficient stereoselective synthesis of 1 alpha,24(R)-dihydroxyvitamin D-3 by the dienyne route. [J].
Fall, Y ;
Torneiro, M ;
Castedo, L ;
Mourino, A .
TETRAHEDRON, 1997, 53 (13) :4703-4714
[7]  
Gravier-Pelletier C, 2003, SYNLETT, P333
[8]   Synthesis and glycosidase inhibitory activity of aminocyclitols with a C6-or a C7-ring [J].
Gravier-Pelletier, C ;
Maton, W ;
Dintinger, T ;
Tellier, C ;
Le Merrer, Y .
TETRAHEDRON, 2003, 59 (44) :8705-8720
[9]   New azadisaccharide analogs as potential antidiabetics [J].
Gravier-Pelletier, C ;
Maton, W ;
Le Merrer, Y .
TETRAHEDRON LETTERS, 2002, 43 (46) :8285-8288
[10]  
GROSS PE, 1995, CLIN CANCER RES, V1, P935