Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Design, Synthesis, Anticancer Activity and Molecular Docking Studies of 2,5-Disubstituted-1,3,4-Oxadiazoles Containing Benzimidazole Moiety

Author(s): Ramamurthy Katikireddy, Ramu Kakkerla *, M.P.S. Murali Krishna, Gandamalla Durgaiah and Y.N. Reddy

Volume 17, Issue 12, 2020

Page: [959 - 968] Pages: 10

DOI: 10.2174/2212797613666200320102503

Price: $65

Abstract

A series of benzimidazolyl-1,3,4-oxadiazoles (7a-k) were synthesized and evaluated for in vitro anticancer activity against HeLa, MCF7, A549, and HEK293 cell lines. The results indicate that compounds 7b, 7j and 7k have shown excellent anticancer activity and while most of the compounds were non toxic to normal HEK293 cell lines. Molecular docking results of the synthesized compounds with the target Pin1 protein were also discussed.

Keywords: 5-Substituted benzimidazoles, benzimidazolyl oxadiazoles, MTT assay, anticancer activity, molecular docking studies.

« Previous Next »
Graphical Abstract

[1]
Ferlay, J.; Shin, H.R.; Bray, F.; Forman, D.; Mathers, C.; Parkin, D.M. Int. J. Cancer, 2010, 127(12), 2893-2917.
[http://dx.doi.org/10.1002/ijc.25516] [PMID: 21351269]
[2]
IARC Cancer Base No 10 2011.
[3]
Harrison, M.R.; Holen, K.D.; Liu, G. Clin. Adv. Hematol. Oncol., 2009, 7(1), 54-64.
[PMID: 19274042]
[4]
Kumar, D.; Patel, G.; Chavers, A.K.; Chang, K.H.; Shah, K. Eur. J. Med. Chem., 2011, 46(7), 3085-3092.
[http://dx.doi.org/10.1016/j.ejmech.2011.03.031] [PMID: 21481985]
[5]
Cragg, G.M.; Grothaus, P.G.; Newman, D. J. Chem. Rev., 2009, 109(7), 3012-3043.
[http://dx.doi.org/10.1021/cr900019j] [PMID: 19422222]
[6]
Gonzales, G.F.; Valerio, L.G., Jr Anticancer. Agents Med. Chem., 2006, 6(5), 429-444.
[http://dx.doi.org/10.2174/187152006778226486] [PMID: 17017852]
[7]
Newman, D.J.; Cragg, G.M. J. Nat. Prod., 2007, 70(3), 461-477.
[http://dx.doi.org/10.1021/np068054v] [PMID: 17309302]
[8]
Lin, C.H.; Li, H.Y.; Lee, Y.C.; Calkins, M.J.; Lee, K.H.; Yang, C.N.; Lu, P. J. Exp. Biol. Med. (Maywood), 2015, 240(3), 403-408.
[http://dx.doi.org/10.1177/1535370215570829] [PMID: 25662955]
[9]
Cheng, C.W.; Tse, E. Front Pharmacol. Frontiers Media SA., 2018, 9(Article- 1367)
[10]
Zhao, S.; Dong, W.B.; Zhang, C.; Li, Q.P.; Kang, L.; Lei, X.P.; Zhai, X.S. Zhongguo Dang Dai Er Ke Za Zhi, 2015, 17(5), 496-501.
[PMID: 26014703]
[11]
Samanta, S.K.; Lee, J.; Hahm, E.R.; Singh, S.V. Mol. Carcinog., 2018, 57(7), 936-946.
[http://dx.doi.org/10.1002/mc.22814] [PMID: 29603395]
[12]
Rustighi, A.; Zannini, A.; Campaner, E.; Ciani, Y.; Piazza, S.; Del Sal, G. Cell Death Differ., 2017, 24(2), 200-211.
[http://dx.doi.org/10.1038/cdd.2016.122] [PMID: 27834957]
[13]
Ansari, K.F.; Lal, C. Eur. J. Med. Chem., 2009, 44(5), 2294-2299.
[http://dx.doi.org/10.1016/j.ejmech.2008.01.022] [PMID: 18316140]
[14]
Ansari, K.F.; Lal, C. Eur. J. Med. Chem., 2009, 44(10), 4028-4033.
[http://dx.doi.org/10.1016/j.ejmech.2009.04.037] [PMID: 19482384]
[15]
Kagthara, P.R.; Shah, N.S.; Doshi, R.K.; Parekh, H.H. Indian J. Chem. B, 1999, 38B(5), 572-576.
[16]
Xue, C.B.; Rafalski, M.; Roderick, J.; Eyermann, C.J.; Mousa, S.; Olson, R.E.; DeGrado, W.F. Bioorg. Med. Chem. Lett., 1996, 6(3), 339-344.
[http://dx.doi.org/10.1016/0960-894X(95)00590-P]
[17]
Thimmegowda, N.R.; Nanjunda Swamy, S.; Kumar, C.S.; Kumar, Y.C.; Chandrappa, S.; Yip, G.W.; Rangappa, K.S. Bioorg. Med. Chem. Lett., 2008, 18(1), 432-435.
[http://dx.doi.org/10.1016/j.bmcl.2007.08.078] [PMID: 17981032]
[18]
Refaat, H.M. Eur. J. Med. Chem., 2010, 45(7), 2949-2956.
[http://dx.doi.org/10.1016/j.ejmech.2010.03.022] [PMID: 20399544]
[19]
Gaba, M.; Singh, D.; Singh, S.; Sharma, V.; Gaba, P. Eur. J. Med. Chem., 2010, 45(6), 2245-2249.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.067] [PMID: 20172630]
[20]
Melchor-Doncel de la Torre, S.; Vázquez, C.; González-Chávez, Z.; Yépez-Mulia, L.; Nieto-Meneses, R.; Jasso-Chávez, R.; Saavedra, E.; Hernández-Luis, F. Bioorg. Med. Chem. Lett., 2017, 27(15), 3403-3407.
[http://dx.doi.org/10.1016/j.bmcl.2017.06.013] [PMID: 28648464]
[21]
Zawawi, N.K.N.A.; Taha, M.; Ahmat, N.; Wadood, A.; Ismail, N.H.; Rahim, F.; Ali, M.; Abdullah, N.; Khan, K.M. Bioorg. Med. Chem., 2015, 23(13), 3119-3125.
[http://dx.doi.org/10.1016/j.bmc.2015.04.081] [PMID: 26001340]
[22]
Rashid, M.; Husain, A.; Mishra, R. Eur. J. Med. Chem., 2012, 54, 855-866.
[http://dx.doi.org/10.1016/j.ejmech.2012.04.027 ] [PMID: 22608854]
[23]
Akhtar, M.J.; Siddiqui, A.A.; Khan, A.A.; Ali, Z.; Dewangan, R.P.; Pasha, S.; Yar, M.S. Eur. J. Med. Chem., 2017, 126, 853-869.
[http://dx.doi.org/10.1016/j.ejmech.2016.12.014] [PMID: 27987485]
[24]
Salahuddin, Shaharyar M.; Mazumder, A.; Abdullah, M. M. Arab. J. Chem., 2017, 10, S503-S508.
[http://dx.doi.org/10.1016/j.arabjc.2012.10.010..]
[25]
Guimarães, C.R.W.; Boger, D.L.; Jorgensen, W.L. J. Am. Chem. Soc., 2005, 127(49), 17377-17384.
[http://dx.doi.org/10.1021/ja055438j] [PMID: 16332087]
[26]
Zarghi, A.; Faizi, M.; Shafaghi, B.; Ahadian, A.; Khojastehpoor, H.R.; Zanganeh, V.; Tabatabai, S.A.; Shafiee, A. Bioorg. Med. Chem. Lett., 2005, 15(12), 3126-3129.
[http://dx.doi.org/10.1016/j.bmcl.2005.04.018] [PMID: 15876530]
[27]
Banerjee, A.G.; Das, N.; Shengule, S.A.; Srivastava, R.S.; Shrivastava, S.K. Eur. J. Med. Chem., 2015, 101, 81-95.
[http://dx.doi.org/10.1016/j.ejmech.2015.06.020] [PMID: 26117820]
[28]
Rapolu, S.; Alla, M.; Bommena, V.R.; Murthy, R.; Jain, N.; Bommareddy, V.R.; Bommineni, M.R. Eur. J. Med. Chem., 2013, 66, 91-100.
[http://dx.doi.org/10.1016/j.ejmech.2013.05.024] [PMID: 23792319]
[29]
Wani, M.Y.; Ahmad, A.; Shiekh, R.A.; Al-Ghamdi, K.J.; Sobral, A.J.F.N. Bioorg. Med. Chem., 2015, 23(15), 4172-4180.
[http://dx.doi.org/10.1016/j.bmc.2015.06.053] [PMID: 26164624]
[30]
Iyer, V.B.; Inturi, G.B.M.B.; Sairam, K.V.; Pujar, G.V. RSC Advances, 2016, 6(29), 24797-24807.
[http://dx.doi.org/10.1039/C6RA01158F]
[31]
Valente, S.; Trisciuoglio, D.; De Luca, T.; Nebbioso, A.; Labella, D.; Lenoci, A.; Bigogno, C. J. Med. Chem., 2014, 57(14), 6259-6265.
[http://dx.doi.org/10.1021/jm500303u] [PMID: 24972008]
[32]
Kaya, B.; Hussin, W.; Yurttaş, L.; Turan-Zitouni, G.; Gençer, H.K.; Baysal, M.; Karaduman, A.B.; Kaplancıklı, Z.A. Drug Res. (Stuttg.), 2017, 67(5), 275-282.
[http://dx.doi.org/10.1055/s-0042-119070] [PMID: 28561221]
[33]
Shaikh, A.; Meshram, J. J. Heterocycl. Chem., 2015, 539(4), 1176-1182.
[http://dx.doi.org/10.1002/jhet.2377]
[34]
Wang, S.; Guan, L.; Zang, J.; Xing, K.; Zhang, J.; Liu, D.; Zhao, L. Molecules 2019, 24((7), E1198), 1-14.
[http://dx.doi.org/10.3390/molecules24071198]
[35]
Ma, T. Bioorg. Med. Chem. Lett., 2019, 29(14), 1859-1863.
[http://dx.doi.org/10.1016/j.bmcl.2018.11.045] [PMID: 31103446]
[36]
Kakkerla, R.; Marri, S.; Krishna, M.P.S.M.; Molgara, P.; Reddy, Y.N. Lett. Org. Chem., 2018, 15(2), 124-132.
[http://dx.doi.org/10.2174/1570178614666170623121207]
[37]
Marri, S.; Kakkerla, R.; Murali Krishna, M.P.S.; Venkat Rajam, M. Heterocycl. Commun., 2018, 24(5), 285-292.
[http://dx.doi.org/10.1515/hc-2018-0137]
[38]
Kakkerla, R.; Marri, S.; Murali Krishna, M.P.S.; Rajam, M.V. Indian J. Chem. B, 2018, 57B(6), 823-829.
[39]
Marri, S.; Kakkerla, R.; Krishna, M.P.S.M.; Lingabathula, H.; Yellu, N.R.; Merugu, R. Indian J. Chem. B, 2019, 58B(1), 109-119.
[40]
Marri, S.; Kakkerla, R.; Krishna, M.P.S.M. Indian J. Chem. B, 2019, 58B(3), 381-386.
[41]
Reddy, K.S.; Srinivasam, N.; Reddy, C.R.; Naveenkumar, K.; Anjaneyulu, Y.; Venkatraman, S.; Battacharya, A.; Mathad, V.T. Org. Process Res. Dev., 2007, 11(1), 81-85.
[http://dx.doi.org/10.1021/op060200g]
[42]
Kurumbail, R.G.; Stevens, A.M.; Gierse, J.K.; McDonald, J.J.; Stegeman, R.A.; Pak, J.Y.; Gildehaus, D.; Miyashiro, J.M.; Penning, T.D.; Seibert, K.; Isakson, P.C.; Stallings, W.C. Nature, 1996, 384(6610), 644-648.
[http://dx.doi.org/10.1038/384644a0] [PMID: 8967954]
[43]
Katikireddy, R.; Kakkerla, R.; Krishna, M.P.S.M.; Durgaiah, G.; Reddy, Y.N.; Satyanarayana, M. Heterocycl. Commun., 2019, 25(1), 27-38.
[http://dx.doi.org/10.1515/hc-2019-0009]
[44]
Botta, M.; Armaroli, S.; Castagnolo, D.; Fontana, G.; Pera, P.; Bombardelli, E. Bioorg. Med. Chem. Lett., 2007, 17(6), 1579-1583.
[http://dx.doi.org/10.1016/j.bmcl.2006.12.101] [PMID: 17254787]
[45]
Trott, O.; Olson, A.J. J. Comput. Chem., 2010, 31(2), 455-461.
[PMID: 19499576]
[46]
Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belew, R.K.; Goodsell, D.S.; Olson, A.J. J. Comput. Chem., 2009, 30(16), 2785-2791.
[http://dx.doi.org/10.1002/jcc.21256] [PMID: 19399780]

Rights & Permissions Print Cite
Article Metrics
41
© 2024 Bentham Science Publishers | Privacy Policy