European Journal of Chemistry 2011, 2(3), 337-341 | doi: https://doi.org/10.5155/eurjchem.2.3.337-341.363 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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.

2_3_337_341_800


Keywords


Indole-3-acetic acid; Reactive oxygen species (ROS); 2-(1H-indol-3-yl)acetyl chloride; Antioxidant activity; Lipid peroxidation; Butylated hydroxy anisole (BHA)

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.3.337-341.363

Links for Article


| | | | | | |

| | | | | | |

| |

Related Articles




Article Metrics

This Abstract was viewed 1876 times | PDF Article downloaded 592 times


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
Novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters: synthesis and a new insight into their antioxidant and antimicrobial potential
Medicinal Chemistry Research  23(4), 1887, 2014
DOI: 10.1007/s00044-013-0793-z
/


[5]. 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
/


[6]. Salakatte Thammaiah Harini, Honnaiah Vijay Kumar, Javarappa Rangaswamy, Nagaraja Naik
Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core
Bioorganic & Medicinal Chemistry Letters  22(24), 7588, 2012
DOI: 10.1016/j.bmcl.2012.10.019
/


[7]. G. Chitra, D. S. Franklin, S. Sudarsan, M. Sakthivel, S. Guhanathan
Preparation, antimicrobial and antioxidant evaluation of indole-3-acetic acid-based pH-responsive bio-nanocomposites
Polymer Bulletin  74(8), 3379, 2017
DOI: 10.1007/s00289-016-1900-3
/


[8]. 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
SN Applied Sciences  1(12), , 2019
DOI: 10.1007/s42452-019-1339-x
/


[9]. 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
Molecular Biology Reports  46(4), 4333, 2019
DOI: 10.1007/s11033-019-04887-4
/


References

[1]. Babior, B. M. Am. J. Med. 2000, 109, 33-44.
http://dx.doi.org/10.1016/S0002-9343(00)00481-2

[2]. Lander, H. M. FASEB J. 1997, 11, 118-124.
PMid:9039953

[3]. Gibson, G. E. Free Radical Biol. Med. 2002, 32, 1061-1070.
http://dx.doi.org/10.1016/S0891-5849(02)00802-X

[4]. Giasson, B. I.; Ischiropoulos, H.; Lee, V. M. Y.; Trojanowski, J. Q. Free Radical Biol. Med. 2002, 32, 1264-1275.
http://dx.doi.org/10.1016/S0891-5849(02)00804-3

[5]. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Farnsworthm, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218-220.
http://dx.doi.org/10.1126/science.275.5297.218
PMid:8985016

[6]. Heinecke, J. W. Free. Radic. Biol. Med. 2002, 32, 1090-1101.
http://dx.doi.org/10.1016/S0891-5849(02)00792-X

[7]. Hazell, L. J.; Baernthaler, G.; Stocker, R. Free Radical Biol. Med. 2001, 31, 1254-1262.
http://dx.doi.org/10.1016/S0891-5849(01)00717-1

[8]. Cuzzocrea, S.; Riley, D. P.; Caputi, A. P.; Salvemini, D. Pharm. Rev. 2001, 53, 135-159.
PMid:11171943

[9]. Saija, A.; Scalese, M.; Lanza, M.; Marzullo, D.; Bonina, F.; Castelli, F. Free Rad. Biol. Med. 1995, 19, 481-486.
http://dx.doi.org/10.1016/0891-5849(94)00240-K

[10]. Bors, W. H.; Michel, C.; Saran, M. Methods Enzymol. 1990, 186, 343-355.
http://dx.doi.org/10.1016/0076-6879(90)86128-I

[11]. You-Zhi, T.; Zai-Qun, L. Bioorg. Med. Chem. 2007, 15, 1903-1913.
http://dx.doi.org/10.1016/j.bmc.2007.01.007

[12]. Lucarini, M.; Pedrielli, P.; Pedulli, G. F.; Valgimigli, L.; Gigmes, D.; Toroda, P. J. Am. Chem. Soc. 1999, 121, 11546-11533.
http://dx.doi.org/10.1021/ja992904u

[13]. Vinson, J. A.; Dabbagh, Y. A.; Serry, M. M.; Jang, J. J Agric. Food Chem. 1995, 43, 2800-2802.
http://dx.doi.org/10.1021/jf00059a005

[14]. Salopek-sondi, B.; Piljac-Zegarac, J.; Magnus, V.; Kopjar, N. J. Biochem. Mole Toxi. 2010, 24, 165-173.
http://dx.doi.org/10.1002/jbt.20323
PMid:20583293

[15]. Olgen, S.; Kilic, Z.; Ada, A. O.; Coban, T. Arch. Pharm. Chem. Life. Sci. 2007, 340, 140-146.

[16]. Gerard, A. P.; Maria A. P.; Mario, S.; Giuseppe, P. Il Farmaco 1998, 53, 161-168.
http://dx.doi.org/10.1016/S0014-827X(97)00016-5

[17]. Andrey, E. S.; Alexander, A. S.; Yuri, N. L.; Tatyana, V. B.; Vladimir, N. B.; Maria, N. P. Bioorg. Med. Chem. 2005, 13, 2285-2291.
http://dx.doi.org/10.1016/j.bmc.2004.12.044

[18]. Alicia, J.; Nestor E.; Massa; Leonor, L.T.; Nora B. O. Vibr. Spect. 2000, 537, 161-178.

[19]. Keith, J. C.; Malcolm, H.T. R. Euro. J. Pharm. 1974, 29, 154-160.
http://dx.doi.org/10.1016/0014-2999(74)90182-4

[20]. Ali, S.; Veena, U.; Edward, G. C.; Mirlinda, B.; Dalian, Z.; Jean-Francois, M.; Kevin, R. C.; Michel, J.; Anthony, O. K.; Rob, D. L.; Edward. J. J. G.; Ralph, P. V.; Richard, D. T. Tetrahedron Asym. 2005, 16, 3094-3098.

[21]. Vijay, K. H.; Gnanendra, C. R.; Channe, G. D.; Naik, N. E. J. Chem. 2008, 5), 1123-1132.

[22]. Vijay, K. H.; Kishor, K. C.; Naik, N. Med. Chem. Res. 2011, 20, 101-108.
http://dx.doi.org/10.1007/s00044-009-9292-7

[23]. Vijay, K. H.; Nagaraja, N. Eur. J. Med. Chem. 2010, 45(1), 2-10.
http://dx.doi.org/10.1016/j.ejmech.2009.09.016
PMid:19846240

[24]. Blois, M. S. Nature 1958, 181, 1199-1199.
http://dx.doi.org/10.1038/1811199a0

[25]. Kamath, S. A.; Ryubin, E. Biochem. Biophys. Res. Comm. 1972, 49, 52-59.
http://dx.doi.org/10.1016/0006-291X(72)90008-3

[26]. Buege, J. A.; Aust, S. T. Methods Enzymol. 1978, 52, 302-310.
http://dx.doi.org/10.1016/S0076-6879(78)52032-6

[27]. Herbert, J. E.; Donald, G. C. Org. Synth. Coll. 1973, 5, 654-654.

[28]. Kappus, H. Lipid peroxidation-Mechnism and biological relevance. Taylor & Francis, 1991.

[29]. Jadhav, S. J.; Nimbalkar, S. S.; Kulkarani, A. D.; Madhavi, D. L. Lipid oxidation in biological and food systems. In: Madhavi, D. L.; Deshpande, S. S.; D. K. Salunke (Eds), Food antioxidants. New York: Marcel Dekker, 1996.

[30]. Janero, D. Free Rad. Bio. Med. 1990, 9, 515-540.
http://dx.doi.org/10.1016/0891-5849(90)90131-2

How to cite


Naik, N.; Kumar, H.; Harini, S. Eur. J. Chem. 2011, 2(3), 337-341. doi:10.5155/eurjchem.2.3.337-341.363
Naik, N.; Kumar, H.; Harini, S. Synthesis and antioxidant evaluation of novel indole-3-acetic acid analogues. Eur. J. Chem. 2011, 2(3), 337-341. doi:10.5155/eurjchem.2.3.337-341.363
Naik, N., Kumar, H., & Harini, S. (2011). Synthesis and antioxidant evaluation of novel indole-3-acetic acid analogues. European Journal of Chemistry, 2(3), 337-341. doi:10.5155/eurjchem.2.3.337-341.363
Naik, Nagaraja, Honnaiah Vijay Kumar, & Salakatte Thammaiah Harini. "Synthesis and antioxidant evaluation of novel indole-3-acetic acid analogues." European Journal of Chemistry [Online], 2.3 (2011): 337-341. Web. 30 Nov. 2020
Naik, Nagaraja, Kumar, Honnaiah, AND Harini, Salakatte. "Synthesis and antioxidant evaluation of novel indole-3-acetic acid analogues" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.2.3.337-341.363

| | | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2011, 2(3), 337-341 | doi: https://doi.org/10.5155/eurjchem.2.3.337-341.363 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.