Conjugation of l-NAME to prenyloxycinnamic acids improves its inhibitory effects on nitric oxide production

Bioorg Med Chem Lett. 2013 May 15;23(10):2933-5. doi: 10.1016/j.bmcl.2013.03.050. Epub 2013 Mar 21.

Abstract

A series of 10 compounds resulting from the conjugation of O-prenylated naturally occurring benzoic and cinnamic acids to l-NAME were synthesized and tested together with the corresponding unprenylated parent molecule as anti-inflammatory agents for their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophages. Results indicated that the coupling between O-geranyl and O-isopentenylcinnamic acids and l-NAME led to products with an enhanced activity when compared to the parent compounds.

MeSH terms

  • Animals
  • Cinnamates / chemistry
  • Cinnamates / pharmacology*
  • Dose-Response Relationship, Drug
  • Lipopolysaccharides / pharmacology
  • Macrophages / chemistry
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • NG-Nitroarginine Methyl Ester / chemistry
  • NG-Nitroarginine Methyl Ester / pharmacology*
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Structure-Activity Relationship

Substances

  • Cinnamates
  • Lipopolysaccharides
  • Nitric Oxide
  • NG-Nitroarginine Methyl Ester