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 50 条
  • [31] Synthesis and glycosidase inhibitory activity of noeurostegine-a new and potent inhibitor of β-glucoside hydrolases
    Rasmussen, Tina Secher
    Jensen, Henrik Helligso
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (02) : 433 - 441
  • [32] Synthesis and protein tyrosine phosphatase inhibitory activity of dephostatin analogs
    Watanabe, T
    Takeuchi, T
    Otsuka, M
    Tanaka, S
    Umezawa, K
    JOURNAL OF ANTIBIOTICS, 1995, 48 (12): : 1460 - 1466
  • [33] Synthesis and creatine kinase inhibitory activity of nonhydrolyzable analogs of phosphocreatine
    Bergnes, G
    KaddurahDaouk, R
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (08) : 1021 - 1026
  • [34] Synthesis of polyhydroxylated cyclohexenyl sulfides and sulfoxides.: Evaluation of their inhibitory activity on α- and β-D-glucosidases
    Lubineau, A
    Billault, I
    CARBOHYDRATE RESEARCH, 1999, 320 (1-2) : 49 - 60
  • [35] SYNTHESIS OF PSEUDO-OLIGOSACCHARIDIC GLYCOSIDASE INHIBITORS .11. SYNTHESIS AND ENZYME-INHIBITORY ACTIVITY OF METHYL ACARVIOSIN ANALOGS HAVING THE ALPHA-MANNO CONFIGURATION
    OGAWA, S
    NAKAMURA, Y
    CARBOHYDRATE RESEARCH, 1992, 226 (01) : 79 - 89
  • [36] Synthesis and glycosidase inhibitory activity of new hexa-substituted C8-glycomimetics
    Andriuzzi, Olivia
    Gravier-Pelletier, Christine
    Bertho, Gildas
    Prange, Thierry
    Le Merrer, Yves
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2005, 1
  • [37] Synthesis of novel pyrimidine nucleoside analogues owning multiple bases/sugars and their glycosidase inhibitory activity
    Thakur, Ravi Kumar
    Mishra, Akansha
    Ramakrishna, K. K. G.
    Mahar, Rohit
    Shukla, Sanjeev K.
    Srivastava, A. K.
    Tripathi, Rama P.
    TETRAHEDRON, 2014, 70 (45) : 8462 - 8473
  • [38] Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics
    Andriuzzi, O
    Gravier-Pelletier, C
    Vogel, P
    Le Merrer, Y
    TETRAHEDRON, 2005, 61 (30) : 7094 - 7104
  • [39] Synthesis and glycosidase inhibitory activity of aminocyclitols with a C6-or a C7-ring
    Gravier-Pelletier, C
    Maton, W
    Dintinger, T
    Tellier, C
    Le Merrer, Y
    TETRAHEDRON, 2003, 59 (44) : 8705 - 8720
  • [40] SYNTHESIS AND ACETYLCHOLINESTERASE INHIBITORY ACTIVITY OF SEVERAL PYRIMIDONE ANALOGS OF HUPERZINE-A
    KOZIKOWSKI, AP
    CAMPIANI, G
    SAXENA, A
    DOCTOR, BP
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) : 283 - 285