Gem-diamine 1-N-iminosugars, a new family of glycosidase inhibitors:: Synthesis and biological activity

被引:8
|
作者
Nishimura, Y [1 ]
机构
[1] Microbial Chem Res Ctr, Shinagawa Ku, Tokyo 1410021, Japan
关键词
D O I
10.3987/REV-05-SR(T)3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Specific inhibitors of glycosidases are useful for unraveling how glycoconjugates regulate biological functions, and also for developing the new drugs for the serious diseases associated with both the biosynthesis and the degradation of glycoconjugate such as cancer, tumor metastasis, inflammatory disorders, viral and bacterial infections and so forth. This article describes the synthesis and biological activity of gem-diamine 1-N-iminosugars, a new class of glycosidase inhibitors, with a nitrogen atom in place of the anomeric carbon. New inhibitors that may mimic the glycopyranosyl cation, the putative intermediate of enzymatic glycosidic hydrolysis, have shown strong and specific inhibition against glycosidases. The inhibitors also illustrate a promising candidate of new drugs for tumor metastasis.
引用
收藏
页码:461 / 488
页数:28
相关论文
共 50 条
  • [21] Synthesis of novel 1-N-iminosugars from chiral nonracemic bicyclic lactams
    Xie, J
    Güveli, T
    Hebbe, S
    Dechoux, L
    TETRAHEDRON LETTERS, 2004, 45 (25) : 4903 - 4906
  • [22] Synthesis and biological evaluation of glycosidase inhibitors:: gem-difluoromethylenated nojirimycin analogues
    Wang, Ruo-Wen
    Qiu, Xiao-Long
    Bols, Mikael
    Ortega-Caballero, Fernando
    Qing, Feng-Ling
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (10) : 2989 - 2997
  • [23] 1-N-iminosugars:: Potent and selective inhibitors of β-glycosidases (vol 120, pg 3007, 1998)
    Ichikawa, Y
    Igarashi, Y
    Ichikawa, M
    Suhara, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) : 5854 - 5854
  • [24] Highly selective synthesis of 1-N-iminosugars of the D-glucose and -glucuronic acid types
    Kim, YJ
    Ichikawa, M
    Ichikawa, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08): : 2599 - 2602
  • [25] Flexible enantiodivergent synthesis and biological activity of mannostatin analogues, new cyclitol glycosidase inhibitors
    Nishimura, Y
    Umezawa, Y
    Adachi, H
    Kondo, S
    Takeuchi, T
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02): : 480 - 488
  • [26] Flexible Enantiodivergent Synthesis and Biological Activity of Mannostatin Analogues, New Cyclitol Glycosidase Inhibitors
    Nishimura, Y.
    Umezawa, Y.
    Adachi, H.
    Kondo, S.
    Journal of Organic Chemistry, 61 (02):
  • [27] Azetidine- and N-carboxylic azetidine-iminosugars as amyloglucosidase inhibitors: synthesis, glycosidase inhibitory activity and molecular docking studies
    Gavale, Kishor S.
    Chavan, Shrawan R.
    Khan, Ayesha
    Joshi, Rakesh
    Dhavale, Dilip D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (23) : 6634 - 6646
  • [28] Proline-catalyzed aldol approach to the synthesis of 1-N-iminosugars of the D-glucuronic acid type
    Chen, Chen
    Yu, Biao
    TETRAHEDRON LETTERS, 2008, 49 (04) : 672 - 674
  • [29] Synthesis of Multibranched Australine Derivatives from Reducing Castanospermine Analogues through the Amadori Rearrangement of gem-Diamine Intermediates: Selective Inhibitors of β-Glucosidase
    Sanchez-Fernandez, Elena M.
    Alvarez, Eleuterio
    Ortiz Mellet, Carmen
    Garcia Fernandez, Jose M.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11722 - 11728
  • [30] The first L-iduronic acid-type 1-N-iminosugars having inhibitory activity of experimental metastasis
    Nishimura, Y
    Satoh, T
    Adachi, H
    Kondo, S
    Takeuchi, T
    Azetaka, M
    Fukuyasu, H
    Iizuka, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) : 3051 - 3052