European Journal of Chemistry 2015, 6(4), 482-487 | doi: https://doi.org/10.5155/eurjchem.6.4.482-487.1325 | Get rights and content

Issue cover





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

One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities


Suresh Seeka (1) , Sirassu Narsimha (2) , Kumaraswamy Battula (3) , Althaf Hussain Shaikh (4) , Savitha Jyostna Tangeda (5) , Vasudeva Reddy Nagavelli (6,*)

(1) Department of Chemistry, KakatiyaUniversity, Warangal, TS, 506009, India
(2) Department of Chemistry, KakatiyaUniversity, Warangal, TS, 506009, India
(3) Department of Chemistry, KakatiyaUniversity, Warangal, TS, 506009, India
(4) Department of Biotechnology, Kakatiya University, Warangal, TS, 506009, India
(5) Department of Chemistry, KakatiyaUniversity, Warangal, TS, 506009, India
(6) Department of Chemistry, KakatiyaUniversity, Warangal, TS, 506009, India
(*) Corresponding Author

Received: 18 Sep 2015 | Revised: 09 Oct 2015 | Accepted: 18 Oct 2015 | Published: 31 Dec 2015 | Issue Date: December 2015

Abstract


In view of pharmacological importance of benzimidazole and 1,2,3-triazole nuclei, we made an effort to synthesize the bi-functional mimic 1,2,3-triazolyl-benzimidazoles through the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction in ionic liquids. The synthesized compounds were characterized by NMR, IR and Mass spectral analysis. The synthesized compounds were screened for antimicrobial and antioxidant activities. A good number of the compounds found to possess potent antioxidant and antimicrobial activities.


Keywords


Ionic liquid; Benzimidazole; 1,2,3-Triazoles; One pot synthesis; Antioxidant activity; Antimicrobial activity

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.6.4.482-487.1325

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1427 times | icon graph PDF Article downloaded 508 times

Funding information


University Grants Commission-Major Research Project, New Delhi, India

Citations

/


[1]. Kumara Swamy Battula, Sirassu Narsimha, Ranjith Kumar Thatipamula, Yellu Narsimha Reddy, Vasudeva Reddy Nagavelli
Synthesis and Biological Evaluation of (N-(3-methoxyphenyl)-4-((aryl-1H -1,2,3-triazol-4-yl)methyl)thiomorpholine-2-carboxamide 1,1-Dioxide Hybrids as Antiproliferative Agents
ChemistrySelect  2(29), 9595, 2017
DOI: 10.1002/slct.201701902
/


[2]. C. P. Kaushik, Manisha Chahal
Synthesis, antimalarial and antioxidant activity of coumarin appended 1,4-disubstituted 1,2,3-triazoles
Monatshefte für Chemie - Chemical Monthly  152(8), 1001, 2021
DOI: 10.1007/s00706-021-02821-8
/


[3]. Chander Prakash Kaushik, Raj Luxmi
Synthesis, antibacterial, and antioxidant activities of naphthyl‐linked disubstituted 1,2,3‐triazoles
Journal of Heterocyclic Chemistry  57(6), 2400, 2020
DOI: 10.1002/jhet.3956
/


[4]. E. Venkatesh, S. Narsimha, N. S. Kumar, N. V. Reddy
One Pot Synthesis and Antitumor Activity of Isoxazole-Pyrimido[4,5-c]isoquinolines
Russian Journal of General Chemistry  90(12), 2444, 2020
DOI: 10.1134/S1070363220120361
/


[5]. Kumara Swamy Battula, Sirassu Narsimha, Ranjith Kumar Thatipamula, Yellu Narsimha Reddy, Vasudeva Reddy Nagavelli
Synthesis and Biological Evaluation of Novel Thiomorpholine 1,1-Dioxide Derived 1,2,3-Triazole Hybrids as Potential Anticancer Agents
ChemistrySelect  2(14), 4001, 2017
DOI: 10.1002/slct.201700524
/


[6]. D. Gouthami, B. Srinivas, M Ravinder
Synthesis of Quinoxlines Containing 1,2,3-Triazoles and Their Anti-Bacterial and Anti-Cancer Activity
Russian Journal of Bioorganic Chemistry  47(4), 882, 2021
DOI: 10.1134/S1068162021040105
/


[7]. Nagavelli Vasudeva Reddy, Sirassu Narsimha, Lavudya Sudhakar, Kumara Swamy Battula, S K Althaf Hussain
N,N′-(hexane-1,6-diyl)bis(N-((1-aryl/alkyl-1H-1,2,3-triazol-4-yl)methyl)-4-methyl benzenesulfonamide): Synthesis, antibacterial, antioxidant, and DNA-cleavage activities
Phosphorus, Sulfur, and Silicon and the Related Elements  191(8), 1118, 2016
DOI: 10.1080/10426507.2016.1146273
/


[8]. Vasudeva Reddy Nagavelli, Satheesh Kumar Nukala, Sirassu Narsimha, Kumara Swamy Battula, Savitha Jyostna Tangeda, Yellu Narasimha Reddy
Synthesis, characterization and biological evaluation of 7-substituted- 4-((1-aryl-1H-1,2,3-triazol-4-yl) methyl)-2H-benzo[b][1,4]oxazin- 3(4H)-ones as anticancer agents
Medicinal Chemistry Research  25(9), 1781, 2016
DOI: 10.1007/s00044-016-1616-9
/


References


[1]. Kamal, S.; Sumit, C.; Sushant K. S.; Pradeep, M. Med. Chem. Res. 2013, 22, 5077-5104.
http://dx.doi.org/10.1007/s00044-013-0476-9

[2]. Balasubramanian, N.; Deepika, S.; Pradeep, K. Med. Chem. Res. 2012, 21, 269-283.
http://dx.doi.org/10.1007/s00044-010-9533-9

[3]. Shivakumar, R.; Pradeepchandran, R. V.; Narasimha, J. K. Eur. J. Chem. 2011, 2, 558-560.
http://dx.doi.org/10.5155/eurjchem.2.4.558-560.275

[4]. Love Kumar, S.; Narsinghani, T.; Anand, S. Med. Chem. Res. 2012, 21, 4330-4334.
http://dx.doi.org/10.1007/s00044-012-9976-2

[5]. Tuncbilek, M.; Kiper, T.; Altanlar, N. Eur. J. Med. Chem. 2009, 44, 1024-1033.
http://dx.doi.org/10.1016/j.ejmech.2008.06.026

[6]. Desai, N. C.; Pandya, D. D.; Joshi, V. V.; Rajpara, K. M.; Vaghani, H. V.; Satodiya, H. M. Med. Chem. Res. 2012, 21, 4463-4472.
http://dx.doi.org/10.1007/s00044-012-9990-4

[7]. Deepkumar, J.; Kalpesh, P. Med. Chem. Res. 2014, 23, 1290-1299.
http://dx.doi.org/10.1007/s00044-013-0732-z

[8]. Afaf, H. E. M.; Fahmy, H. H.; Ali Abdelwahed, S. H. Molecules 2000, 5, 1429-1438.
http://dx.doi.org/10.3390/51201429

[9]. Ravishankara, D. K.; Chandrashekara, P. G. Eur. J. Chem. 2012, 3, 363-366.
http://dx.doi.org/10.5155/eurjchem.3.3.363-366.616

[10]. Guruswamy, B.; Arul, R. K.; Chaitanya, M. V. S. R. K.; Darsi, S. S. P. K. Eur. J. Chem. 2013, 4, 329-335.
http://dx.doi.org/10.5155/eurjchem.4.4.329-335.792

[11]. Tonelli, M.; Matteo, S.; Bruno, T.; Federica, N.; Giuseppina, S.; Fabio, S.; Giuseppe, P.; Sabrina, P.; Vito, B.; Gabriele, G.; Sylvain, B.; Cristina, I.; Roberta, L.; Paolo, L. C. Bioorg. Med. Chem. 2010, 18, 2937-2953.
http://dx.doi.org/10.1016/j.bmc.2010.02.037

[12]. Angela, R.; Alba, C.; Erik, D. C.; Anna, M. M.; Pietro, M.; Christophe, P.; Maria, Z. Il Farmaco 2002, 57, 819-823.
http://dx.doi.org/10.1016/S0014-827X(02)01300-9

[13]. Ruiming, Z.; Kevin, R.; Ayres, J. C.; Drach, L. B.; Townsend. J. Med. Chem. 1996, 39, 3477-3482.

[14]. Garuti, L.; Roberti, M.; G. Gentilomi, G. II Farmaco 2000, 55, 35-39.
http://dx.doi.org/10.1016/S0014-827X(99)00117-2

[15]. Ravishankara, D. K.; Chandrashekara, P. G. Eur. J. Chem. 2012, 3, 359‐362.
http://dx.doi.org/10.5155/eurjchem.3.3.359-362.607

[16]. Ravishankara, D. K.; Chandrashekara, P. G. Eur. J. Chem. 2012, 3, 359-362.
http://dx.doi.org/10.5155/eurjchem.3.3.359-362.607

[17]. Kavitha, C. S. A.; Kallappa M. H.; Harisha R. S. E. J. Med. Chem. 2010, 45, 2048-2054.
http://dx.doi.org/10.1016/j.ejmech.2010.01.029

[18]. Kaushik, D.; Ahmed Khan, S.; Gita C. Med. Chem. Res. 2012, 21, 459-467.
http://dx.doi.org/10.1007/s00044-011-9552-1

[19]. Galal, S. A.; Abdelsamie, A. S.; Rodriguez, M. L.; Kerwin, S. M. El Diwani, H. I. Eur. J. Chem. 2010, 1, 67-72.
http://dx.doi.org/10.5155/eurjchem.1.2.67-72.1

[20]. Nofal. Z. M.; Soliman, E. A.; Abd El-Karim, S. S.; Elzahar, M. I.; Srour, A. M.; Dhavan, S. S.; Maher, T. J. Acta P. Pharm. Drug Res. 2011, 68, 519-534.

[21]. Ahmed A. E. R.; Hassan, Y. A. E. Mini-Rev. Med. Chem. 2013, 13, 399- 407.

[22]. Ali, E. S.; Omer, O. A.; Sama, A. A. Eur. J. Chem. 2012, 3, 356-358.
http://dx.doi.org/10.5155/eurjchem.3.3.356-358.621

[23]. Meldal, M.; Christian, W. T.; Christensen, C. J. Org. Chem. 2002, 67, 3057-3064.
http://dx.doi.org/10.1021/jo011148j

[24]. Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Org. Chem. 2004, 69, 2386-2393.
http://dx.doi.org/10.1021/jo035292b

[25]. Cristina, G. O.; Jagerovic, N.; Goya, P.; Alkorta, I.; Elguero, J.; Cuberes, R.; Dordal, A. Arkivoc 2010, 2, 127-147.

[26]. Akhtar, T.; Hameed, S.; Khan, K. M.; Khan, A.; Choudhary, M. I. J. Enzym Inhib. Med. Ch. 2010, 25, 572-576.
http://dx.doi.org/10.3109/14756360903389864

[27]. Alvarez, S.; San, F.; Aquaro, S. D. C.; Perno, C, F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185- 4194.
http://dx.doi.org/10.1021/jm00050a015

[28]. Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K. M. J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953-970.
http://dx.doi.org/10.1021/jm990373e

[29]. Narsimha, S.; Ranjith, K. T.; Satheesh, K. N.; Yakoob, S.; Vasudeva, R. N. Med. Chem. Res. 2014, 23, 5321-5327.
http://dx.doi.org/10.1007/s00044-014-1076-z

[30]. Huisgen. R. Angew. Chem. 1963, 75, 604-637.

[31]. David, A.; Francesco, F.; Oriana, P.; Ferdinando, P.; Ennio, Z.; Luigi, V. J. Org. Chem. 2005, 70, 6526-6529.
http://dx.doi.org/10.1021/jo0500378

[32]. Sharpless, K. B.; Vsevolod, V. R.; Luke, G. G.; Valery, V. F. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
http://dx.doi.org/10.1002/1521-3773(20020617)41:12<2024::AID-ANIE2024>3.0.CO;2-O

[33]. Firouzeh, N.; Ali, E. J. Appl. Chem. 2012, 7, 29-33.

[34]. Jorapur, Y. R.; Jeong, J. M.; C. hi, D. Y. Tetrahedron Lett. 2006, 47, 2435-2438.
http://dx.doi.org/10.1016/j.tetlet.2006.01.129

[35]. Cinzia, C.;, Daniela, P. Green Chem. 2003, 5, 193-197

[36]. Cinzia, C.; Paolo, P.; Daniela, P. Green Chem. 2006, 8, 277-281.
http://dx.doi.org/10.1039/B509851C

[37]. Alberto, M.; Alessandra, V.; Cinzia, C.; Bernardo, M.; Alessandro, D. J. Org. Chem. 2008, 73, 2458-2461.
http://dx.doi.org/10.1021/jo7026454

[38]. Ya-Bin, Z.; Ze-Yi, Y.; Yong-Min, Liang. Tetrahedron Lett. 2006, 47, 1545-1549.

[39]. Barral, K.; Moorhouse, A. D.; Moses, J. E. Org. Lett. 2007, 9, 1809-1811.
http://dx.doi.org/10.1021/ol070527h

[40]. Moorhouse, A. D.; Moses, J. E. Synlett. 2008, 14, 2089-2092.

[41]. Parekh, J.; Chanda, S. V. Turk. J. Biol. 2007, 31, 53-58.

[42]. Cosentino, S.; Tuberoso, C. I. G.; Pisano, B.; Satta, M.; Mascia, V.; Arzedi, E.; Palmas, F. Lett. Appl. Microbiol. 1999, 29, 130-135.
http://dx.doi.org/10.1046/j.1472-765X.1999.00605.x

[43]. Gul, M. Z.; Farhan, A.; Anand, K. K.; Insaf, A. Q.; Irfan, A. G. BMC Complem. Altern. Med. 2013, 13, 53, 1-12.

[44]. Ramesh, G.; Janardhan, B.; Ranjith Kumar, T.; Althaf Hussain, S. K.; Rajitha, B. RSC Adv. 2015, 5, 33562-33569.
http://dx.doi.org/10.1039/C5RA07726E


How to cite


Seeka, S.; Narsimha, S.; Battula, K.; Shaikh, A.; Tangeda, S.; Nagavelli, V. Eur. J. Chem. 2015, 6(4), 482-487. doi:10.5155/eurjchem.6.4.482-487.1325
Seeka, S.; Narsimha, S.; Battula, K.; Shaikh, A.; Tangeda, S.; Nagavelli, V. One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities. Eur. J. Chem. 2015, 6(4), 482-487. doi:10.5155/eurjchem.6.4.482-487.1325
Seeka, S., Narsimha, S., Battula, K., Shaikh, A., Tangeda, S., & Nagavelli, V. (2015). One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities. European Journal of Chemistry, 6(4), 482-487. doi:10.5155/eurjchem.6.4.482-487.1325
Seeka, Suresh, Sirassu Narsimha, Kumaraswamy Battula, Althaf Hussain Shaikh, Savitha Jyostna Tangeda, & Vasudeva Reddy Nagavelli. "One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities." European Journal of Chemistry [Online], 6.4 (2015): 482-487. Web. 4 Dec. 2021
Seeka, Suresh, Narsimha, Sirassu, Battula, Kumaraswamy, Shaikh, Althaf, Tangeda, Savitha, AND Nagavelli, Vasudeva. "One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

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.6.4.482-487.1325

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2015, 6(4), 482-487 | doi: https://doi.org/10.5155/eurjchem.6.4.482-487.1325 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2021  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 2010-2021 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.