In a continuation of our program to develop a new class of antimicrobial and antioxidant agents, 13 novel 3-substituted indole derivatives incorporating biologically active heterocycles were synthesized and evaluated for their in vitro antimicrobial activity. Among the synthesized compounds, 3-(7H-imidazo[2,1-c][1,2,4]triazol-5-yl)-1H-indole showed activity against E. faecalis equal to that of ampicillin and 50% higher activity than ampicillin against S. aureus and B. subtilis. Also, 3-(7H-imidazo[2,1-c][1,2,4]triazol-5-yl)-1H-indole was found to exhibit strong in vitro antifungal activity against Candida albicans, Aspergillus niger, and Penicillium sp. The antioxidant activity of the obtained indole derivatives was also studied using 2,2'-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid).
Similar content being viewed by others
References
Singla, R.; Gupta, K. B.; Upadhyay, S.; Dhiman, M.; Jaitak, V. Eur. J. Med. Chem. 2018, 146, 206.
Sidhu, J. S.; Singla, R.; Jaitak, M.; Jaitak, V. Anti-Cancer Agents Med. Chem. 2015, 16, 160.
Festa, A. A. Chem. Heterocycl. Compd. 2018, 54, 22. [Khim. Geterotsikl. Soedin. 2018, 54, 22.]
Leboho, T. C.; Michael, J. P.; van Otterlo, W. A. L.; van Vuuren, S. F.; de Koning, C. B. Bioorg. Med. Chem. Lett. 2009, 19, 4948.
Kumar, A.; Saxena, K. K.; Gurtu, S.; Sinha, J. N.; Shanker, K. Indian Drugs 1986, 24, 1.
El-Gendy, A. A.; Abdou Naida, A.; Sarhan El-Taher, Z.; El-Banna, H. A. Alexandria J. Pharm. Sci. 1993, 7, 99.
Kuduk, S. D.; Chang, R. K.; Wai, J. M.-C.; Di Marco, C. N.; Cofre, V.; DiPardo, R. M.; Cook, S. P.; Cato, M. J.; Jovanovska, A.; Urban, M. O.; Leitl, M.; Spencer, R. H.; Kane, S. A.; Hartman, G. D.; Bilodeau, M. T. Bioorg. Med. Chem. Lett. 2009, 19, 4059.
Radwan, M. A. A.; Ragab, E. A.; Sabry, N. M.; El-Shenawy, S. M. Bioorg. Med. Chem. 2007, 15, 3832.
Diss, L. B.; Robinson, S. D.; Wu, Y.; Fidalgo, S.; Yeoman, M. S.; Patel, B. A. ACS Chem. Neurosci. 2013, 4, 879.
Xiong, W.-N.; Yang, C.-G.; Jiang, B. Bioorg. Med. Chem. 2001, 9, 1773.
Zhu, S.-L.; Ji, S.-J.; Su, X.-M.; Sun, C.; Liu, Y. Tetrahedron Lett. 2008, 49, 1777.
Zhu, S.-L.; Ji, S.-J.; Zhao, K.; Liu, Y. Tetrahedron Lett. 2008, 49, 2578.
Thirumurugan, P.; Nandakumar, A.; Muralidharan, D.; Perumal, P. T. J. Comb. Chem. 2010, 12, 161.
Behbehani, H.; Ibrahim, H. M.; Makhseed, S.; Mahmoud, H. Eur. J. Med. Chem. 2011, 46, 1813.
Mohamed, M. S.; Youns, M. M.; Ahmed, N. M. Med. Chem. Res. 2014, 23, 3374.
El-Mekabaty, A. Synth. Commun. 2015, 45, 2271.
Fadda, A. A.; El-Mekabaty, A.; Mousa, I. A.; Elattar, K. M. Synth. Commun. 2014, 44, 1579.
El-Mekabaty, A.; Etman, H. A.; Mosbah, A. J. Heterocycl. Chem. 2016, 53, 894.
El-Mekabaty, A.; Mesbah, A.; Fadda, A. A. J. Heterocycl. Chem. 2017, 54, 916.
Bergman, J.; Bäckvall, J.-Erling; Lindström, J.-Olov Tetrahedron 1973, 29, 971.
Chavez, D. E.; Parrish, D. A. J. Heterocycl. Chem. 2009, 46, 88.
Marathe, S.; Karnik, A. V. Chem. Heterocycl. Compd. 2017, 53, 604. [Khim. Geterotsikl. Soedin. 2017, 53, 604.]
Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627.
Lopez, S. N.; Sortino, M.; Escalante, A.; Campos, F.; Correa, R.; Cechinel-Filho, V.; Nunes, R. J.; Zacchino, S. A. Arzneim. Forsch. 2003, 53, 280.
Wang, J. J.; Liu, T. Y.; Yin, P. H.; Wu, C. W.; Chern, Y. T.; Chi, C. W. Anticancer Res. 2000, 20, 3067.
Bansode, T. N.; Shelke, J. V.; Dongre, V. G. Eur. J. Med. Chem. 2009, 44, 5094.
Abdel-Aziz, H. A.; Mekawey, A. A. I. Eur. J. Med. Chem. 2009, 44, 4985.
Manna, K.; Agrawal, Y. K. Bioorg. Med. Chem. Lett. 2009, 19, 2688.
Hall, A.; Billinton, A.; Brown, S. H.; Clayton, N. M.; Chowdhury, A.; Giblin, G. M. P.; Goldsmith, P.; Hayhow, T. G.; Hurst, D. N.; Kilford, I. R.; Naylor, A.; Passingham, B.; Winyard, L. Bioorg. Med. Chem. Lett. 2008, 18, 3392.
Sharipova, S. M.; Kalinin, A. A. Chem. Heterocycl. Compd. 2017, 53, 36. [Khim. Geterotsikl. Soedin. 2017, 53, 36.]
Abdel-Aziz, H. A.; Mekawey, A. A. I.; Dawood, K. M. Eur. J. Med. Chem. 2009, 44, 3637.
Khalaj, A.; Nakhjiri, M.; Negahbani, A. S.; Samadizadeh, M.; Firoozpour, L.; Rajabalian, S.; Samadi, N.; Faramarzi, M. A.; Adibpour, N.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem. 2011, 46, 65.
Owoseni, A. A.; Ajayi, A. J. Med. Appl. Biosci. 2010, 2, 64.
Solomakos, N.; Govaris, A.; Koidis, P.; Botsoglou, N. Meat Sci. 2008, 80, 159.
Pandey, A.; Singh, P. Asian J. Plant Sci. Res. 2011, 1, 69.
Abu-Shanab, B.; Adwan, G.; Abu-Safiya, D.; Jarrar, N.; Adwan, K. Turk. J. Biol. 2004, 28, 99.
Akinjogunla, O. J.; Eghafona, N. O.; Enabulele, I. O.; Mboto, C. I.; Ogbemudia, F. O. Afr. J. Pharm. Pharmacol. 2010, 4, 402.
Shimada, K.; Fujikawa, K.; Yahara, K.; Nakamura, T. J. Agric. Food Chem. 1992, 40, 945.
Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radical Biol. Med. 1999, 26, 1231.
All of the tested microorganisms were selected based on their clinical and pharmacological importance and were kindly provided by Dr. Metwally, Prof. of Microbiology, Botany Department, Tanta University, Egypt.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(6), 618–624
Rights and permissions
About this article
Cite this article
El-Mekabaty, A., El-Shora, H.M. Synthesis and evaluation of some novel 3-hetarylindole derivatives as antimicrobial and antioxidant agents. Chem Heterocycl Comp 54, 618–624 (2018). https://doi.org/10.1007/s10593-018-2317-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-018-2317-8