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
  • [41] Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine
    Pearson, WH
    Guo, LY
    TETRAHEDRON LETTERS, 2001, 42 (47) : 8267 - 8271
  • [42] SYNTHESIS AND INHIBITORY ACTIVITY OF NEW ETHYLENEDIOXYQUINONES AS ANALOGS OF COENZYME-Q
    BOWMAN, CM
    WIKHOLM, RJ
    BOLER, J
    BOGENTOFT, CB
    FOLKERS, K
    JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (09) : 988 - 991
  • [43] Synthesis and Matrix Metalloproteinase-12 Inhibitory Activity of Ageladine A Analogs
    Ando, Naoki
    Terashima, Shiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (05) : 579 - 596
  • [44] Synthesis and biological evaluation of phloroglucinol derivatives possessing -glycosidase, acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase inhibitory activity
    Burmaoglu, Serdar
    Yilmaz, Ali O.
    Taslimi, Parham
    Algul, Oztekin
    Kilic, Deryanur
    Gulcin, Ilhami
    ARCHIV DER PHARMAZIE, 2018, 351 (02)
  • [45] Pseudosugars, 41 -: Synthesis and glycosidase inhibitory activity of 5a-carba-α-DL-fucopyranosylamine and -galactopyranosylamine
    Ogawa, S
    Sekura, R
    Maruyama, A
    Yuasa, H
    Hashimoto, H
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (11) : 2089 - 2093
  • [46] SYNTHESIS AND DNA GYRASE INHIBITORY ACTIVITY OF NOVEL AZA-ANALOGS OF FLAVONES
    SUI, ZH
    OHEMENG, K
    VANNGUYEN
    ALTOM, J
    WEIDNERWELLS, M
    FRAGA, S
    KANOJIA, R
    FERNANDEZ, J
    HILLIARD, J
    KRAUSE, H
    BARRETT, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 177 - MEDI
  • [47] Synthesis of Novel Nitroxoline Analogs with Potent Cathepsin B Exopeptidase Inhibitory Activity
    Van de Walle, Tim
    Briand, Marina
    Mitrovic, Ana
    Sosic, Izidor
    Gobec, Stanislav
    Kos, Janko
    Persoons, Leentje
    Daelemans, Dirk
    De Jonghe, Steven
    Ubiparip, Zorica
    Desmet, Tom
    Van Hecke, Kristof
    Mangelinckx, Sven
    D'hooghe, Matthias
    CHEMMEDCHEM, 2020, 15 (24) : 2477 - 2490
  • [48] Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs
    Ando, Naoki
    Terashima, Shiro
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (16) : 4495 - 4499
  • [49] Synthesis and inhibitory activity against phosphatidylinositol 4-kinase of echiguanine analogs
    Saito, Y
    Kato, K
    Umezawa, K
    NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (4-5): : 713 - 714
  • [50] SYNTHESIS AND INHIBITORY ACTIVITY OF DIFLUOROKETONE SUBSTRATE-ANALOGS OF N-MYRISTOYLTRANSFERASE
    NEDER, KM
    FRENCH, SA
    MILLER, SPF
    TETRAHEDRON, 1994, 50 (33) : 9847 - 9864