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Synthesis and antioxidant evaluation of novel indole-3-acetic acid analogues
Nagaraja Naik (1,*)
, Honnaiah Vijay Kumar (2) , Salakatte Thammaiah Harini (3) (1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(2) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(*) Corresponding Author
Received: 05 Dec 2010 | Accepted: 14 Mar 2011 | Published: 30 Sep 2011 | Issue Date: September 2011
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.
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DOI: 10.5155/eurjchem.2.3.337-341.363
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Citations
[1]. Javarappa Rangaswamy, Honnaiah Vijay Kumar, Salakatte Thammaiah Harini, Nagaraja Naik
Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds: A new class of antimicrobials and antioxidants
Arabian Journal of Chemistry 10, S2685, 2017
DOI: 10.1016/j.arabjc.2013.10.012
[2]. G. Chitra, D. S. Franklin, S. Guhanathan
Indole-3-acetic acid based tunable hydrogels for antibacterial, antifungal and antioxidant applications
Journal of Macromolecular Science, Part A 54(3), 151, 2017
DOI: 10.1080/10601325.2017.1265401
[3]. Nagaraja Naik, Vishwanath Sharath, Honnaiah Vijay Kumar
Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials
European Journal of Chemistry 3(2), 214, 2012
DOI: 10.5155/eurjchem.3.2.214-219.588
[4]. Salakatte Thammaiah Harini, Honnaiah Vijay Kumar, Sannenahalli Krishnegowda Peethambar, Javarappa Rangaswamy, Nagaraja Naik
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DOI: 10.1007/s00044-013-0793-z
[5]. Honnaiah Vijay Kumar, Prasanth Kumar, Javarappa Rangaswamy, Kirugunda Udayakumar Sindhu, Nagaraja Naik
5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties
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[6]. Chitra G., Franklin D.S., Sudarsan S., Sakthivel M., Guhanathan S.
Indole-3-acetic acid/diol based pH-sensitive biological macromolecule for antibacterial, antifungal and antioxidant applications
International Journal of Biological Macromolecules 95, 363, 2017
DOI: 10.1016/j.ijbiomac.2016.11.068
[7]. Salakatte Thammaiah Harini, Honnaiah Vijay Kumar, Javarappa Rangaswamy, Nagaraja Naik
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[8]. G. Chitra, D. S. Franklin, S. Sudarsan, M. Sakthivel, S. Guhanathan
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Polymer Bulletin 74(8), 3379, 2017
DOI: 10.1007/s00289-016-1900-3
[9]. G. Chitra, M. S. Selvi, D. S. Franklin, S. Sudarsan, M. Sakthivel, S. Guhanathan
pH-sensitive biopolymeric hydrogel-based on indole-3-acetic acid for wound healing and anti-cancer applications
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[10]. P. Thyriyalakshmi, K. V. Radha
Fabrication of chitosan-bis (4-formyl-2 methoxy phenyl carbonate) Schiff base nanoparticles and evaluation of their antioxidant and anticancer properties
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DOI Link: https://doi.org/10.5155/eurjchem.2.3.337-341.363
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