Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis

Chembiochem. 2006 Jan;7(1):165-73. doi: 10.1002/cbic.200500321.

Abstract

A novel 5-membered iminocyclitol derivative was found to be a potent and selective inhibitor of the glycoprotein-processing alpha-glucosidase with a Ki value of 53 nM. This compound was further derivatized to antiviral agents against Japanese encephalitis virus, dengue virus serotype 2 (DEN-2), human SARS coronavirus, and human beta-hexosaminidase (Ki = 2.6 nM), a new target for the development of osteoarthritis therapeutics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Combinatorial Chemistry Techniques
  • Dengue Virus / drug effects
  • Encephalitis Virus, Japanese / drug effects
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Heterocyclic Compounds, 1-Ring / chemical synthesis
  • Heterocyclic Compounds, 1-Ring / chemistry
  • Heterocyclic Compounds, 1-Ring / pharmacology*
  • Humans
  • Imino Pyranoses* / chemical synthesis
  • Imino Pyranoses* / chemistry
  • Imino Pyranoses* / pharmacology
  • Microbial Sensitivity Tests
  • Models, Biological
  • Models, Molecular
  • Osteoarthritis / enzymology*
  • Severe acute respiratory syndrome-related coronavirus / drug effects
  • Structure-Activity Relationship
  • Substrate Specificity
  • beta-N-Acetylhexosaminidases / antagonists & inhibitors

Substances

  • Antiviral Agents
  • Enzyme Inhibitors
  • Heterocyclic Compounds, 1-Ring
  • Imino Pyranoses
  • Glycoside Hydrolases
  • beta-N-Acetylhexosaminidases