Antioxidant activity of DL omega-phenyl-amino acid octyl esters with anti-inflammatory activity. Correlation of the structure with lipophilicity

Arzneimittelforschung. 2001;51(6):485-8. doi: 10.1055/s-0031-1300067.

Abstract

The antioxidant activities (in vitro) and the lipophilicity (as RM values) of 12 DL-omega-phenyl-amino acid octyl esters with anti-inflammatory/analgesic activities were studied. The tested compounds were found to interact with 1,1-diphenyl-2-picrylhydrazyl stable free radical (DPPH), whereas most of them were essentially inactive in other tests. DL-2-Amino-4-(4-aminophenyl)butyric acid octyl ester was found to be the most active. The anti-inflammatory activity does not seem to be connected with O2-. or HO. scavenging activity at least under the experimental conditions applied. However, the interaction with DPPH was found to be correlated with their anti-inflammatory activity. Between the lipophilicity and the anti-inflammatory activity only a poor relationship exists. For a subgroup of the derivatives of the phenyl glycine octyl ester (1-8) a significant correlation was found between the RM values and the calculated clog P lipophilicity.

MeSH terms

  • Amino Acids / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Chemical Phenomena
  • Chemistry, Physical
  • Chromatography, Thin Layer
  • Enzyme Inhibitors / pharmacology
  • Esters / chemical synthesis*
  • Esters / pharmacology*
  • Free Radical Scavengers
  • Glucuronidase / antagonists & inhibitors
  • Glucuronidase / metabolism
  • Indicators and Reagents
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antioxidants
  • Enzyme Inhibitors
  • Esters
  • Free Radical Scavengers
  • Indicators and Reagents
  • Glucuronidase