Synthesis, antioxidative and antiviral activity of hydroxycinnamic acid amides of thiazole containing amino acid

Amino Acids. 2009 Jul;37(2):383-8. doi: 10.1007/s00726-008-0165-z. Epub 2008 Oct 14.

Abstract

The synthesis and the biological (antioxidant and antiviral) activities of novel hydroxycinnamic acid amides of a thiazole containing TFA.valine-4-carboxylic acid ethyl ester are reported. The amides have been synthesized from p-coumaric, ferulic and sinapic acids with the corresponding TFA.valine-thiazole-4-carboxylic acid ethyl ester using the coupling reagent N-ethyl-N'-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) and 4-(dimethylamino) pyridine (DMAP) as a catalyst. The antioxidant properties of the newly synthesized amides have been studied for then antioxidative activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH)* test. The newly synthesized compounds have been tested against the replication in vitro of influenza virus A (H3N2) and human herpes virus 1 and 2 (HSV-1 and HSV-2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Animals
  • Antioxidants* / chemical synthesis
  • Antioxidants* / chemistry
  • Antioxidants* / metabolism
  • Antiviral Agents* / chemical synthesis
  • Antiviral Agents* / chemistry
  • Antiviral Agents* / metabolism
  • Biphenyl Compounds / metabolism
  • Cell Line
  • Coumaric Acids* / chemical synthesis
  • Coumaric Acids* / chemistry
  • Coumaric Acids* / metabolism
  • Free Radical Scavengers / metabolism
  • Free Radicals / metabolism
  • Herpesvirus 1, Human / physiology
  • Herpesvirus 2, Human / physiology
  • Humans
  • Mice
  • Molecular Structure
  • Picrates / metabolism
  • Thiazoles / chemistry*
  • Virus Replication

Substances

  • Amino Acids
  • Antioxidants
  • Antiviral Agents
  • Biphenyl Compounds
  • Coumaric Acids
  • Free Radical Scavengers
  • Free Radicals
  • Picrates
  • Thiazoles
  • 1,1-diphenyl-2-picrylhydrazyl