Synthesis of N-, S-, and C-glycoside castanospermine analogues with selective neutral alpha-glucosidase inhibitory activity as antitumour agents

Chem Commun (Camb). 2010 Aug 7;46(29):5328-30. doi: 10.1039/c0cc00446d. Epub 2010 Jun 15.

Abstract

sp(2)-Iminosugar-type castanospermine analogues bearing an alpha-configured N-, S-, or C-linked pseudoanomeric group have been designed as selective inhibitors of the neutral alpha-glucosidases involved in N-glycoprotein processing; evaluation in breast cancer cell growth indicated a significant antiproliferative potential that was dependent on the nature of the pseudoanomeric group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolase Inhibitors*
  • Glycosides / chemistry*
  • Humans
  • Indolizines / chemistry*
  • Indolizines / pharmacology
  • Molecular Structure
  • Monosaccharides / chemistry*

Substances

  • Antineoplastic Agents
  • C-glycoside
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Glycosides
  • Indolizines
  • Monosaccharides
  • castanospermine