Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production

Bioorg Med Chem Lett. 2012 Apr 1;22(7):2534-5. doi: 10.1016/j.bmcl.2012.01.135. Epub 2012 Feb 8.

Abstract

A number of oroxylin A analogs were prepared and evaluated for their inhibitory activities against iNOS-mediated nitric oxide (NO) production from LPS-stimulated BV2 cells. The analogs were synthesized from purchased 2'-hydroxy-4,5,6-trimethoxyacetophenone and aldehydes in 3 steps. Among the tested compounds, several analogs (3b, 3c, 3d, 3f) exhibited strong inhibitory activities. Especially, the analog with 4-nitrophenyl group (3b) showed stronger inhibitory activity (IC(50)=4.73 μM) than that of wogonin (IC(50)=7.80 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry
  • Aldehydes / chemistry
  • Animals
  • Anti-Anxiety Agents / chemical synthesis*
  • Anti-Anxiety Agents / pharmacology
  • Cell Line, Transformed
  • Flavanones / pharmacology
  • Flavonoids / chemical synthesis*
  • Flavonoids / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages / cytology
  • Macrophages / drug effects
  • Mice
  • Microglia / cytology
  • Microglia / drug effects
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / antagonists & inhibitors*
  • Nitric Oxide Synthase Type II / metabolism
  • Nitrophenols / chemistry

Substances

  • 2-hydroxyl-4,5,6-trimethoxyacetophenone
  • Acetophenones
  • Aldehydes
  • Anti-Anxiety Agents
  • Flavanones
  • Flavonoids
  • Lipopolysaccharides
  • Nitrophenols
  • 4-nitrophenyl
  • Nitric Oxide
  • 5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one
  • Nitric Oxide Synthase Type II
  • wogonin