European Journal of Chemistry

Synthesis of 3H-imidazo[4,5-b] pyridine with evaluation of their anticancer and antimicrobial activity

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Published: Mar 31, 2017
DOI: https://doi.org/10.5155/eurjchem.8.1.25-32.1522
Keywords:
Anticancer activity, Substituted aldehydes, Antimicrobial activity, Conventional synthesis, Microwave-assisted synthesis, 5-Bromopyridine-2, 3-diamine
Section
Research Article
Issue
Vol. 8 No. 1 (2017): March 2017
Dates
Received 2016-12-20
Accepted 2017-01-15
Published 2017-03-31


Main Article Content

Rohini Narayan Shelke
Department of Chemistry, Deogiri College, Aurangabad, 431005, India
Dattatraya Navnath Pansare
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, India
Chandrakant Dhondiram Pawar
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, India
Arun Khandu Deshmukh
Rao Bahadhur Narayanrao Borawake College Shrirampur, Ahmednagar, 413709, India
Rajendra Pandu Pawar
Department of Chemistry, Deogiri College, Aurangabad, 431005, India
Saroj Ram Bembalkar
Department of Chemistry, Deogiri College, Aurangabad, 431005, India

Abstract

Microwave assisted and conventional synthetic methods of new 6-bromo-2-(substituted)-3H-imidazo[4,5-b]pyridine and its derivatives are described, which were obtained in reduced reaction times, higher yields, cleaner reactions than previously described methods. All the synthesized compounds were characterized, and screened for their anticancer and antimicrobial activity. Among synthesized compounds 3b and 3k shows prominent antibacterial activity and compound 3f shows both antibacterial and antifungal activity. Compounds 3h and 3j shows prominent anticancer activity against the both breast cancer cell lines, MCF-7 and BT-474. These results suggest that the imidazo[4,5-b]pyridine moiety may serve as a new promising template for synthesis of anticancer and antimicrobial agents and further study is required for evaluation of their mechanism of action.


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Shelke, R. N.; Pansare, D. N.; Pawar, C. D.; Deshmukh, A. K.; Pawar, R. P.; Bembalkar, S. R. Synthesis of 3H-imidazo[4,5-B] Pyridine With Evaluation of Their Anticancer and Antimicrobial Activity. Eur. J. Chem. 2017, 8, 25-32.

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References

[1]. Abdel-Wahab, B. F.; Awad, G. E. A.; Badria, F. A. Eur. J. Med. Chem. 2011, 46, 1505-1511.
https://doi.org/10.1016/j.ejmech.2011.01.062

[2]. He, J.; Xie, J. Acta Pharm. Sin. 2011, 8, 674-680.

[3]. Rybak, M. J.; Akins, R. L. Drugs 2001, 61, 1-7.
https://doi.org/10.2165/00003495-200161010-00001

[4]. Liu, J. F.; Wilson, C. J.; Ye, P.; Sprague, K.; Sargent, K.; Si, Y.; Beletski, G.; Yohannes, D.; Ng, S. C. Bioorg. Med. Chem. Lett. 2006, 16, 686-690.
https://doi.org/10.1016/j.bmcl.2005.10.022

[5]. Liu, J. F.; Kaselj, M.; Isome, Y.; Ye, P.; Sargent, K.; Sprague, K.; Cherrak, D.; Wilson, C. J.; Si, Y.; Yohannes, D.; Ng, S. C. J. Comb. Chem. 2006, 8, 7-10.
https://doi.org/10.1021/cc050108g

[6]. Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S. Eur. J. Med. Chem. 2009, 44, 4244-4248.
https://doi.org/10.1016/j.ejmech.2009.05.021

[7]. Liaras, K.; Geronikaki, A.; Glamoclija, J.; Ciric, A.; Sokovic, M. Bioorg. Med. Chem. 2011, 19 (10), 3135-3140.
https://doi.org/10.1016/j.bmc.2011.04.007

[8]. Kim, H. S.; Jadhav, J. R.; Jung, S. J.; Kwak, J. H. Bioorg. Med. Chem. Lett. 2013, 23, 4315-4318.
https://doi.org/10.1016/j.bmcl.2013.05.098

[9]. Mungra, D. C.; Kathrotiya, H. G.; Ladani, N. K.; Patel, M. P.; Patel, R. G. Chin. Chem. Lett. 2012, 12, 1367-1370.
https://doi.org/10.1016/j.cclet.2012.11.007

[10]. Desai, N. C.; Shihory, N. R.; Kotadiya, G. M.; Desai, P. Eur. J. Med. Chem. 2014, 82, 480-489.
https://doi.org/10.1016/j.ejmech.2014.06.004

[11]. Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; De Clercq, E.; Balzarini, J. Eur. J. Med. Chem. 2009, 44, 2347-2353.
https://doi.org/10.1016/j.ejmech.2008.08.010

[12]. Olender, D.; Zwawiak, J.; Lukianchuk, V.; Lesyk, R.; Kropacz, A.; Fojutowski, A.; Zaprutko, L. Eur. J. Med. Chem. 2009, 44, 645-652.
https://doi.org/10.1016/j.ejmech.2008.05.016

[13]. Puratchikody,; Doble, M. Bioorg. Med. Chem. 2007, 15, 1083-1090.

[14]. Achar, K. C. S.; Hosamani, K. M.; Seetharama reddy, H. R. Eur. J. Med. Chem. 2010, 45, 2048-2054.
https://doi.org/10.1016/j.ejmech.2010.01.029

[15]. Gupta, P.; Hameed, S.; Jain, R. Eur. J. Med. Chem. 2004, 39, 805-814.
https://doi.org/10.1016/j.ejmech.2004.05.005

[16]. Hranjec, M.; Starcevic, K.; Piantanida, I.; Kralj, M.; Marjanovic, M.; Hasani, M.; Westman, G.; Karminski-Zamola, G. Eur. J. Med. Chem. 2008, 43, 2877-2890.
https://doi.org/10.1016/j.ejmech.2008.02.010

[17]. Martinez, V.; Burgos, V.; Alvarez-Builla, J.; Fernandez, G.; Domingo, A.; Garcia-Nieto, R.; Gago, F.; Manzanares, I.; Cuevas, C.; Vaquero, J. J. J. Med. Chem. 2004, 47, 1136-1148.
https://doi.org/10.1021/jm0310434

[18]. Aleksandrova, E. V.; Kravchenko, A. N.; Kochergin, P. M. Chem. Heterocycl. Compd. 2011, 47, 261-289.
https://doi.org/10.1007/s10593-011-0754-8

[19]. Kim, H. S.; Jadhav, J. R.; Jung, S. J.; Kwak, J. H. Bioorg. Med. Chem. Lett. 2013, 23, 4315-4318.
https://doi.org/10.1016/j.bmcl.2013.05.098

[20]. Fortuna, G. C.; Barresi, V.; Berellini, G.; Musumarra, G. Bioorg. Med. Chem. 2008, 16, 4150-4169.
https://doi.org/10.1016/j.bmc.2007.12.042

[21]. Nicolaou, K. C.; Scarpelli, R.; Bollbuck, B.; Werschkun, B.; Pereira, M. M. M.; Wartmann, M.; Altmann, K. H.; Zaharevitz, D.; Gussio, R.; Giannakakou, P. Chem. Biol. 2000, 7, 593-599.
https://doi.org/10.1016/S1074-5521(00)00006-5

[22]. Temple, C. J.; Rose, J. D.; Comber, R. N.; Rener, G. A. J. Med. Chem. 1987, 30, 1746-1751.
https://doi.org/10.1021/jm00393a011

[23]. Cristalli, G.; Vittori, S.; Eleuteri, A.; Grifantini, M.; Volpini, R.; Lupidi, G.; Capolongo, L.; Pesenti, E. J. Med. Chem. 1991, 34, 2226-2230.
https://doi.org/10.1021/jm00111a044

[24]. Banie, H.; Sinha, A.; Thomas, R. J.; Sircar, J. C.; Richards, M. L. J. Med. Chem. 2007, 50, 5984-5993.
https://doi.org/10.1021/jm0704907

[25]. Mader, M.; de Dios, A.; Shih, C.; Bonjouklian, R.; Li, T.; White, W.; de Uralde, B. L.; Sanchez-Martinez, C.; del Prado, M.; Jaramillo, C.; de Diego, E.; Martin Cabrejas, L. M.; Dominguez, C.; Montero, C.; Shepherd, T.; Dally, R.; Toth, J. E.; Chatterjee, A.; Pleite, S.; Blanco-Urgoiti, J.; Perez, L.; Barberis, M.; Lorite, M. J.; Jambrina, E.; Nevill Jr., C. R.; Lee, P. A.; Schultz, R. C.; Wolos, J. A.; Li, L. C.; Campbell, R. M.; Anderson, B. D. Bioorg. Med. Chem. Lett. 2008, 18, 179-183.
https://doi.org/10.1016/j.bmcl.2007.10.106

[26]. Feng, D. M.; Wai, J. M.; Kuduk, S. D.; Ng, C.; Murphy, K. L.; Ransom, R. W.; Reiss, D.; Chang, R. S. L.; Harrell, C. M.; MacNeil, T.; Tang, C.; Prueksaritanont, T.; Freidinger, R. M.; Pettiboneb, D. J.; Bocka, M. Bioorg. Med. Chem. Lett. 2005, 15, 2385-2388.
https://doi.org/10.1016/j.bmcl.2005.02.077

[27]. Wang, Li.; Wang, Y.; Tian, H.; Yao, Y.; Shao, J.; Liu, B. J. Fluorine Chem. 2006, 127, 1570-1573.
https://doi.org/10.1016/j.jfluchem.2006.08.005

[28]. Sangshetti, J. N.; Kokare, N. D.; Kotharkar, S. A.; Shinde, D. B. Chin. Chem. Lett. 2008, 19, 762-766.
https://doi.org/10.1016/j.cclet.2008.05.007

[29]. Kathrotiya, H. G.; Patel, N. A.; Patel, R. G.; Patel, M. P. Chin. Chem. Lett. 2012, 23, 273-276.
https://doi.org/10.1016/j.cclet.2011.11.022

[30]. Karimi-Jaberi, Z.; Barekat, M. Chin. Chem. Lett. 2010, 21, 1183-1186.
https://doi.org/10.1016/j.cclet.2010.06.012

[31]. Wang, X. B.; He, L.; Jian, T. Y.; Ye, S. Chin. Chem. Lett. 2012, 23, 13-16.
https://doi.org/10.1016/j.cclet.2011.09.018

[32]. Mekheimer, R. A.; Hameed, A. M. A.; Mansour, S. A. A.; Sadek, K. U. Chin. Chem. Lett. 2009, 20, 812-814.
https://doi.org/10.1016/j.cclet.2009.02.017

[33]. Varma, R. S. Green Chem. 1999, 1, 43-55.
https://doi.org/10.1039/a808223e

[34]. Larhed, M.; Hallberg, A. Drug Disc. Today 2001, 6(8), 406-416.
https://doi.org/10.1016/S1359-6446(01)01735-4

[35]. Hanel, H.; Raether, W. Mycoses 1988, 31, 148.
https://doi.org/10.1111/j.1439-0507.1988.tb03718.x

[36]. Daouk, K. D.; Dagher, M. S.; Sattout, J. E. J. Food Protect. 1995, 58, 1147.
https://doi.org/10.4315/0362-028X-58.10.1147

[37]. Booth, C.; Fungal Culture Media, In Methods in Microbiology, J. R. Norris, D. W. Ribbons, Eds.; Academic Press: London and New York, 1971; pp 49-94.

[38]. Espinel-Ingroff, A. J. Clin. Microbiol. 2001, 39, 1360.
https://doi.org/10.1128/JCM.39.4.1360-1367.2001

[39]. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Jonathan, T. W.; Heidi, B.; Susan, K.; Michael, R. B.; J. Natl. Cancer Inst. 1990, 82, 1107-1112.
https://doi.org/10.1093/jnci/82.13.1107

[40]. Vichai, V.; Kirtikara, K. Nat. Proto. 2006, 1, 1112-1116.
https://doi.org/10.1038/nprot.2006.179

[41]. Pansare, D. N.; Mulla, N. A.; Pawar, C. D.; Shende, V. R.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2014, 24, 3569-3573.
https://doi.org/10.1016/j.bmcl.2014.05.051

[42]. Darandale, S. N.; Pansare, D. N.; Mulla, N. A.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2013, 23, 2632-2635.
https://doi.org/10.1016/j.bmcl.2013.02.099

[43]. Darandale, S. N.; Mulla, N. A.; Pansare, D. N.; Sangshetti, J. N.; Shinde, D. B. Eur. J. Med. Chem. 2013, 65, 527-532.
https://doi.org/10.1016/j.ejmech.2013.04.045

[44]. Pansare, D. N.; Shinde, D. B. Tetrahedron Lett. 2014, 55, 1107-1110.
https://doi.org/10.1016/j.tetlet.2013.12.113

[45]. Pansare, D. N.; Shinde, D. B. Open Chem. J. 2015, 2, 40-46;
https://doi.org/10.2174/1874842201502010040

[46]. Pawar, C. D.; Sarkate, A. P.; Karnik, K. S.; Bahekar, S. S.; Pansare, D. N.; Shelke, R. N.; Jawale, C. S.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2016, 26, 3525-3528.
https://doi.org/10.1016/j.bmcl.2016.06.030

[47]. Pansare, D. N.; Shinde, D. B. Res. Rev. J. Chem. 2015, 4 (1), 8-14.

[48]. Shelke, R. N.; Pansare, D. N.; Pawar, C. D.; Shinde, D. B.; Thore, S. N.; Pawar, R. P; Bembalkar, S. R. Res. Rev. J. Chem. 2016, 5(2), 29-36.

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Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, India
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