European Journal of Chemistry 2012, 3(2), 214-219 | doi: https://doi.org/10.5155/eurjchem.3.2.214-219.588 | Get rights and content

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Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials


Nagaraja Naik (1,*) , Vishwanath Sharath (2) , Honnaiah Vijay Kumar (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 Organic Chemistry, Indian Institute of Science, Bangalore, 560012, India
(*) Corresponding Author

Received: 14 Jan 2012 | Revised: 20 Feb 2012 | Accepted: 21 Feb 2012 | Published: 30 Jun 2012 | Issue Date: June 2012

Abstract


Two series of novel indole-2-carboxylic acid derivatives is reported. In the first series, N-substituted derivatives (3a-h) were synthesized via acylation of indole-2-carboxylic acid followed by aldol condensation reaction. Whereas, in the second series, indole-2-carboxamides (5a-g) were synthesized through conversion of acid to its acid chloride followed by coupling of substituted anilines. Structures of the newly synthesized compounds were confirmed by elemental analysis and spectral IR, 1H NMR and mass data and were screened for antioxidant activity. Among the first series, compound 3g showed higher antioxidant activity and whereas, in the second series compounds 5b and 5c exhibited potential antioxidant activity. Compounds 3g, 5b and 5c exhibited for its enhanced antioxidant activity.

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Keywords


DPPH; Antioxidant activity; Substituted anilines; Indole-2-carboxylic acid; Indole-2-carboxamide; Butylated hydroxy anisole

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DOI: 10.5155/eurjchem.3.2.214-219.588

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Funding information


Indian Institute of Science, Bangalore, India

Citations

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[2]. Fares Hezam Al-Ostoot, D.V. Geetha, Yasser Hussein Eissa Mohammed, P. Akhileshwari, M.A. Sridhar, Shaukath Ara Khanum
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DOI: 10.1016/j.molstruc.2019.127244
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[3]. Fares Hezam Al-Ostoot, Jigmat Stondus, Sumati Anthal, Geetha Doddenahally Venkatesh, Yasser Hussein Eissa Mohammed, Mandayam Anandalwar Sridhar, Shaukath Ara Khanum, Rajni Kant
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DOI: 10.5155/eurjchem.10.3.234-238.1874
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[4]. Honnaiah Vijay Kumar, Prasanth Kumar, Javarappa Rangaswamy, Kirugunda Udayakumar Sindhu, Nagaraja Naik
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DOI: 10.5155/eurjchem.6.4.394-403.1297
/


References


[1]. Yen, G. C.; Chen, H. Y. J. Agric. Food. Chem. 1995, 43, 27-32.
http://dx.doi.org/10.1021/jf00049a007

[2]. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd edition, Oxford, London, 1999, 246-350.

[3]. Block, G. Nutr. Rev. 1992, 50, 207-213.
http://dx.doi.org/10.1111/j.1753-4887.1992.tb01329.x

[4]. Rice-Evans, A. C.; Miller, N. J.; Paganga, G. Free Radical Biol. Med. 1996, 20, 933-956.
http://dx.doi.org/10.1016/0891-5849(95)02227-9

[5]. Sudha, K.; Rao, A.; Rao, S.; Rao, A. Neurol. India 2003, 51, 60-62.
PMid:12865518

[6]. Halliwell, B. Drugs Aging 2001, 18, 685-716.
http://dx.doi.org/10.2165/00002512-200118090-00004

[7]. Sundberg, R. J. Indoles, Academic Press, San Diego, 1996.

[8]. Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49.
http://dx.doi.org/10.1039/b006897g
PMid:11245399

[9]. Ninomiya, I. J. Nat. Prod. 1992, 55, 541-564.
http://dx.doi.org/10.1021/np50083a001

[10]. Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Gao, Q.; King, H. D.; Kozlowski, E. S.; Meng, Z.; Lapaglia, M. A.; Mattson, G. K.; Molski, T. F.; Taber, M. T.; Lodge, N. J.; Mattson, R. J.; Macor, J. E. Bioorg. Med. Chem. Lett. 2009, 4031-4033.
http://dx.doi.org/10.1016/j.bmcl.2009.06.026

[11]. Bandini, M.; Melloni, A.; Umani-Ronchi. Angew. Chem., Int. Ed. 2004, 43, 550-556.
http://dx.doi.org/10.1002/anie.200301679
PMid:14743405

[12]. Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173.
http://dx.doi.org/10.1021/ja017255c
PMid:11841277

[13]. Jensen, K. B.; Thorhange, J.; Hazel, R. G.; Jorgenson, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
http://dx.doi.org/10.1002/1521-3773(20010105)40:1<160::AID-ANIE160>3.0.CO;2-S

[14]. Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109-2114.
http://dx.doi.org/10.1021/jo026550s
PMid:12636368

[15]. Bartoli, G.; Bartolacci, M.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2003, 68, 4594-4597.
http://dx.doi.org/10.1021/jo034303y
PMid:12762781

[16]. Yoshiaki, N.; Masato, Y.; Youichi, I.; Masnobu, H.; Sakae, U. J. Am. Chem. Soc. 2002, 124, 11846-11847.
http://dx.doi.org/10.1021/ja027023t
PMid:12358517

[17]. Wenkert, E.; Angell, E. C.; Ferreira, V. F.; Michelotti, E. L.; Piettre, S. R.; Sheu, J. H.; Swindell, C. S. J. Org. Chem. 1986, 51, 2343-2351.
http://dx.doi.org/10.1021/jo00362a031

[18]. 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

[19]. 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

[20]. Nagaraja, N.; Vijay, K. H.; Harini, S. T. Eur. J. Chem. 2011, 2(3), 337-341.
http://dx.doi.org/10.5155/eurjchem.2.3.337-341.363

[21]. Blois, M. S. Nature 1958, 26, 1199-1200.
http://dx.doi.org/10.1038/1811199a0

[22]. Re, R.; Pellergini, N.; Proteggenete, A.; Pannala, A.; Yang, M.; Rice Evans, C. Free Radic. Biol. Med. 1999, 26, 1231-1237.
http://dx.doi.org/10.1016/S0891-5849(98)00315-3

[23]. Oyaizu, M. Jpn. J. Nut. 1986, 44, 307-315.
http://dx.doi.org/10.5264/eiyogakuzashi.44.307

[24]. Apak, R.; Guclu, K.; Ozyurek, M.; Celik, S. E. Microchim Acta. 2008, 160, 413-419.
http://dx.doi.org/10.1007/s00604-007-0777-0


How to cite


Naik, N.; Sharath, V.; Kumar, H. Eur. J. Chem. 2012, 3(2), 214-219. doi:10.5155/eurjchem.3.2.214-219.588
Naik, N.; Sharath, V.; Kumar, H. Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials. Eur. J. Chem. 2012, 3(2), 214-219. doi:10.5155/eurjchem.3.2.214-219.588
Naik, N., Sharath, V., & Kumar, H. (2012). Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials. European Journal of Chemistry, 3(2), 214-219. doi:10.5155/eurjchem.3.2.214-219.588
Naik, Nagaraja, 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 [Online], 3.2 (2012): 214-219. Web. 29 May. 2023
Naik, Nagaraja, Sharath, Vishwanath, AND Kumar, Honnaiah. "Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials" European Journal of Chemistry [Online], Volume 3 Number 2 (30 June 2012)

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