Synthesis and antioxidant evaluation of novel indole-3-acetic acid analogues
Open Access
- 30 September 2011
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 2 (3), 337-341
- https://doi.org/10.5155/eurjchem.2.3.337-341.363
Abstract
Indole-3-acetic acid (1) on reaction with thionyl chloride, afforded 2-(1H-indol-3-yl)acetyl chloride (2), which was further treated with aniline and various substituted anilines through base condensation reaction to obtain respected indole-3-acetic acid derivatives (3-9). The structures of all new compounds were elucidated by elemental analysis, Mass, IR, 1H NMR and 13C NMR and spectroscopic techniques. All the compounds were screened for their antioxidant activities by applying in vitro methods like 2,2-diphenyl-1-picryl hydrazyl (DPPH) free radical scavenging assay and inhibition of microsomal lipid peroxidation (LPO) assay. Butylated hydroxy anisole (BHA) was used as a reference antioxidant compound and the comparative study with newly synthesized compounds was also done. Among the analogues, compound 9 bearing electron donating methoxy substituent in addition to the phenolic moiety showed predominant activity. It is conceivable from these studies that the coupling of aniline and substituted anilines is the most important feature for the significant antioxidant activity of indole-3-acetic acid analogues studied.Keywords
This publication has 21 references indexed in Scilit:
- Free-radical-scavenging effect of carbazole derivatives on AAPH-induced hemolysis of human erythrocytesBioorganic & Medicinal Chemistry, 2007
- The relationship between oxidative/nitrative stress and pathological inclusions in Alzheimer’s and Parkinson’s diseases1,2Free Radical Biology & Medicine, 2002
- Interactions of oxidative stress with cellular calcium dynamics and glucose metabolism in Alzheimer’s disease1,2Free Radical Biology & Medicine, 2002
- Oxidized amino acids: culprits in human atherosclerosis and indicators of oxidative stress1,2Free Radical Biology & Medicine, 2002
- Correlation between intima-to-media ratio, apolipoprotein B-100, myeloperoxidase, and hypochlorite-oxidized proteins in human atherosclerosisFree Radical Biology & Medicine, 2001
- Phagocytes and oxidative stressThe American Journal of Medicine, 2000
- Bond Dissociation Energies of the N−H Bond and Rate Constants for the Reaction with Alkyl, Alkoxyl, and Peroxyl Radicals of Phenothiazines and Related CompoundsJournal of the American Chemical Society, 1999
- Cancer Chemopreventive Activity of Resveratrol, a Natural Product Derived from GrapesScience, 1997
- Flavonoids as antioxidant agents: Importance of their interaction with biomembranesFree Radical Biology & Medicine, 1995
- [36] Flavonoids as antioxidants: Determination of radical-scavenging efficienciesMethods in Enzymology, 1990