Amplification of the inhibitory activity of miglitol by monofluorination

Bioorg Med Chem Lett. 2009 Oct 1;19(19):5673-4. doi: 10.1016/j.bmcl.2009.08.012. Epub 2009 Aug 7.

Abstract

Selective monofluorination of the alpha-glycosidase inhibitor and antidiabetic agent Miglitol at position C2 creates an competitive inhibitor of five times higher activity than the parent compound. Its screening against a panel of human cell lines showed a low cytotoxicity therefore making this compound an interesting candidate for further clinical investigations.

MeSH terms

  • 1-Deoxynojirimycin / analogs & derivatives*
  • 1-Deoxynojirimycin / chemical synthesis
  • 1-Deoxynojirimycin / chemistry
  • 1-Deoxynojirimycin / toxicity
  • Cell Line
  • Glycoside Hydrolase Inhibitors*
  • Halogenation
  • Humans
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry*
  • Hypoglycemic Agents / toxicity
  • alpha-Glucosidases / metabolism

Substances

  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • miglitol
  • 1-Deoxynojirimycin
  • alpha-Glucosidases