Esters of some non-steroidal anti-inflammatory drugs with cinnamyl alcohol are potent lipoxygenase inhibitors with enhanced anti-inflammatory activity

Bioorg Med Chem Lett. 2015 Nov 15;25(22):5028-31. doi: 10.1016/j.bmcl.2015.10.036. Epub 2015 Oct 19.

Abstract

Novel esters of non steroidal anti-inflammatory drugs, α-lipoic acid and indol-3-acetic acid with cinnamyl alcohol were synthesised by a straightforward method and at high yields (60-98%). They reduced acute inflammation more than the parent acids and are potent inhibitors of soybean lipoxygenase. Selected structures decreased plasma lipidemic indices in Triton-induced hyperlipidemia to rats. Therefore, the synthesised compounds may add to the current knowledge about agents acting against various inflammatory disorders.

Keywords: Cinnamyl esters; Dyslipidemia; Inflammation; Lipoxygenase inhibition; Non steroidal anti-inflammatory drugs.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use
  • Carrageenan
  • Cinnamates / chemical synthesis
  • Cinnamates / pharmacology*
  • Cinnamates / therapeutic use
  • Edema / chemically induced
  • Edema / drug therapy
  • Esters
  • Glycine max
  • Hyperlipidemias / chemically induced
  • Hyperlipidemias / drug therapy
  • Indoleacetic Acids / chemistry
  • Lipoxygenase Inhibitors / chemical synthesis
  • Lipoxygenase Inhibitors / pharmacology*
  • Lipoxygenase Inhibitors / therapeutic use
  • Polyethylene Glycols
  • Propanols / chemistry*
  • Propionates / chemical synthesis
  • Propionates / pharmacology*
  • Propionates / therapeutic use
  • Rats
  • Thioctic Acid / chemistry

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Cinnamates
  • Esters
  • Indoleacetic Acids
  • Lipoxygenase Inhibitors
  • Propanols
  • Propionates
  • cinnamyl 2-(4-isobutylphenyl)propanoate
  • Polyethylene Glycols
  • indoleacetic acid
  • Thioctic Acid
  • Carrageenan
  • cinnamyl alcohol
  • tyloxapol