Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as alpha-glucosidase inhibitors

Bioorg Med Chem Lett. 2008 Mar 1;18(5):1659-62. doi: 10.1016/j.bmcl.2008.01.055. Epub 2008 Jan 19.

Abstract

A series of 8-aminomethylated derivatives (1a-1j) were prepared by Mannich reaction of oroxylin A (1) with appropriate primary or secondary amines and para-formaldehyde. All the compounds were tested for their alpha-glucosidase inhibition activity against both yeast and rat intestinal alpha-glucosidase. Some of the compounds demonstrated significantly better alpha-glucosidase inhibitory activity than the parent compound (oroxylin A).

MeSH terms

  • Animals
  • Flavonoids / chemistry*
  • Flavonoids / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Intestines / enzymology
  • Rats
  • Saccharomyces cerevisiae / enzymology
  • Structure-Activity Relationship

Substances

  • Flavonoids
  • Glycoside Hydrolase Inhibitors
  • 5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one