Synthesis, characterization and radical scavenging activity of aromatic amine conjugates of 5-aminosalicylic acid

Abstract

5-Aminosalicylic acid is an anti-inflammatory drug used in the treatment of inflammatory bowel diseases including ulcerative colitis and Crohn’s disease. Due to its rapid and extensive absorption in the upper gastro-intestinal tract, substantial amount of 5-aminosalicylic acid is already lost before reaching the site of action, i.e. the colon. In order to prevent this loss of drug, carrier linked prodrug approach has been used and azo prodrugs have been synthesized with a purpose of colon targeting. The present research describes the synthesis and characterization of azo prodrugs of 5-aminosalicylic acid with aromatic amines. The synthesized prodrugs were tested for antioxidant activity using DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging activity. All the synthesized compounds were found to possess mild to moderate radical scavenging activity.

KEY WORDS: 5-Aminosalicylic acid, Antioxidant, Inflammatory bowel disease, Prodrugs

Bull. Chem. Soc. Ethiop. 2014, 28(3), 475-480.

DOI: http://dx.doi.org/10.4314/bcse.v28i3.17