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
  • [31] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues
    Berecibar, A
    Grandjean, C
    Siriwardena, A
    CHEMICAL REVIEWS, 1999, 99 (03) : 779 - 844
  • [32] Fluorinated piperidine iminosugars and their N-alkylated derivatives: Synthesis, conformational analysis, immunosuppressive and glycosidase inhibitory activity studies
    Bhuma, Naresh
    Burade, Sachin S.
    Louat, Thierry
    Herman, Jean
    Kawade, Sonali
    Doshi, Pooja J.
    Dhavale, Dilip D.
    TETRAHEDRON, 2018, 74 (08) : 852 - 858
  • [33] Skeletal rearrangement of seven-membered iminosugars: Synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors
    Mondon, Martine
    Lecornue, Frederic
    Guillard, Jerome
    Nakagawa, Shinpei
    Kato, Atsushi
    Bleriot, Yves
    BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (16) : 4803 - 4812
  • [34] Quaternary Indolizidine and Indolizidone Iminosugars as Potential Immunostimulating and Glycosidase Inhibitory Agents: Synthesis, Conformational Analysis, Biological Activity, and Molecular Docking Study
    Pawar, Nitin J.
    Parihar, Vijay Singh
    Khan, Ayesha
    Joshi, Rakesh
    Dhavale, Dilip D.
    JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (19) : 7820 - 7832
  • [35] A general strategy towards the synthesis of 1-N-iminosugar type glycosidase inhibitors:: demonstration by the synthesis of D- as well as L-glucose type iminosugars (isofagomines)
    Pandey, G
    Kapur, M
    TETRAHEDRON LETTERS, 2000, 41 (45) : 8821 - 8824
  • [36] DIAMINE AND TRIAMINE ANALOGS AND DERIVATIVES AS INHIBITORS OF DEOXYHYPUSINE SYNTHASE - SYNTHESIS AND BIOLOGICAL-ACTIVITY
    LEE, YB
    PARK, MH
    FOLK, JE
    JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (16) : 3053 - 3061
  • [37] New oligomers of conduritol-F and muco-inositol.: Synthesis and biological evaluation as glycosidase inhibitors
    Freeman, S
    Hudlicky, T
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) : 1209 - 1212
  • [38] Synthesis and biological activity of some new N-1-substituted quinolones
    Deshmukh, MB
    Shinde, BS
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 5 (03) : 235 - 236
  • [39] Design, Synthesis and Biological Activity of New Carbamate Cholinesterase Inhibitors
    Malucka, Lucia Ungvarska
    Csollei, Jozef
    CHEMICKE LISTY, 2022, 116 (06): : 372 - 380
  • [40] New N,N-dimethylcarbamate inhibitors of acetylcholinesterase: design synthesis and biological evaluation
    De Vita, Daniela
    Pandolfi, Fabiana
    Ornano, Luigi
    Feroci, Marta
    Chiarotto, Isabella
    Sileno, Ilaria
    Pepi, Federico
    Costi, Roberta
    Di Santo, Roberto
    Scipione, Luigi
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2016, 31 : 106 - 113