Synthesis and glycosidase inhibitory activity of novel (2-phenyl-4H-benzopyrimedo[2,1-b]-thiazol-4-yliden)acetonitrile derivatives

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7011-4. doi: 10.1016/j.bmcl.2012.10.025. Epub 2012 Oct 13.

Abstract

A series of (2-phenyl-4H-benzopyrimodo[2,1-b][1,3]thiazol-4-yliden-4-yliden)acetonitrile derivatives have been prepared by ring transformation reaction of 4-(methylthio)-2-oxo-6-aryl-2H-pyrane-3-carbonitriles. The yield of ring transformation product is moderate to good. Furthermore the glycosidase inhibitory activities were tested by using α-amylase and α-glucosidase pancreatic, intestinal and liver enzymes, responsible for hyperglycemia in type II diabetes. The results revealed that all compounds exhibit significant glycosidase inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemical synthesis
  • Acetonitriles / chemistry*
  • Acetonitriles / metabolism
  • Acetonitriles / pharmacology*
  • Amylases / antagonists & inhibitors
  • Amylases / metabolism
  • Animals
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / metabolism
  • Intestines / enzymology
  • Liver / enzymology
  • Mice
  • Pancreas / enzymology
  • Protein Binding
  • Swine
  • alpha-Glucosidases / metabolism

Substances

  • Acetonitriles
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • Amylases
  • alpha-Glucosidases
  • acetonitrile