Antioxidant activity of DL omega-phenyl-amino acid octyl esters with anti-inflammatory activity. Correlation of the structure with lipophilicity.
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.
Kontogiorgis
C A
CA
Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotelian University of Thessaloniki, Greece.
Hadjipavlou-Litina
D J
DJ
Schulz
E
E
D000596:Amino Acids / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002855:Chromatography, Thin Layer; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004952:Esters / Q000138:chemical synthesis* / Q000494:pharmacology*; D016166:Free Radical Scavengers; D005966:Glucuronidase / Q000037:antagonists & inhibitors / Q000378:metabolism; D007202:Indicators and Reagents; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000596:Amino Acids; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D004791:Enzyme Inhibitors; D004952:Esters; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D005966:Glucuronidase