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Letters in Organic Chemistry

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

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Research Article

Design, Synthesis and Biological Evaluation of 3-(3,4,5-Trimethoxyphenyl)- 5-(2-(5-arylbenzo[b]thiophen-3-yl)oxazol-5-yl)isoxazole Derivatives as Anticancer Agents

Author(s): Syndla Premalatha, G. Rambabu, Islavathu Hatti and Dittakavi Ramachandran*

Volume 17, Issue 5, 2020

Page: [345 - 351] Pages: 7

DOI: 10.2174/1570178616666191004105445

Price: $65

Abstract

A new series of 3-(3,4,5-trimethoxyphenyl)-5-(2-(5-arylbenzo[b]thiophen-3-yl)oxa zol-5- yl)isoxazole derivatives were designed and synthesized. All these derivatives were evaluated for their anticancer activity against various human cancer cell lines such as MCF-7 (breast cancer), A549 (lung cancer), DU-145 (prostate cancer) and MDA MB-231 (breast cancer)-four human cancer cell lines by using MTT assay. Here, etoposide was used as a standard reference drug and most of the compounds were exhibited good anticancer activity with respect to cell lines. Among all compounds, five compounds 11b, 11c, 11f, 11i and 11j showed more potent activity than standard drug, in which, compound 11f was the most promising compound.

Keywords: Isoxazole, raloxifene, MTT assay, anticancer activity, MCF-7, prostate cancer.

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[1]
Garcia, M.; Jemal, A.; Ward, E.M.; Center, M.M.; Hao, Y.; Siegel, R.L.; Thun, M.J. Global cancer facts & figures; American Cancer Society: Atlanta, 2007.
[2]
Anand, P.; Kunnumakkara, A.B.; Sundaram, C.; Harikumar, K.B.; Tharakan, S.T.; Lai, O.S.; Sung, B.; Aggarwal, B.B. Pharm. Res., 2008, 25(9), 2097-2116.
[http://dx.doi.org/10.1007/s11095-008-9661-9] [PMID: 18626751]
[3]
Kenneth, W.; Bert, V. The genetic basis of human cancer, McGraw-Hill, Medical Pub; Division, 2005.
[4]
Reddy, N.B.; Burra, V.R.; Ravindranath, L.K.; Sreenivasulu, R.; Kumar, V.N. Monatsh. Chem., 2016, 147, 593-598.
[http://dx.doi.org/10.1007/s00706-016-1685-y]
[5]
Reddy, N.B.; Burra, V.R.; Ravindranath, L.K.; Kumar, V.N.; Sreenivasulu, R.; Sadanandam, P. Monatsh. Chem., 2016, 147, 599-604.
[http://dx.doi.org/10.1007/s00706-016-1684-z]
[6]
Hatti, I.; Sreenivasulu, R.; Jadav, S.S.; Jayaprakash, V.; Kumar, C.G.; Raju, R.R. Med. Chem. Res., 2015, 24, 3305-3313.
[http://dx.doi.org/10.1007/s00044-015-1375-z]
[7]
Sreenivasulu, R.; Reddy, K.T.; Sujitha, P.; Kumar, C.G.; Raju, R.R. Bioorg. Med. Chem., 2019, 27(6), 1043-1055.
[http://dx.doi.org/10.1016/j.bmc.2019.02.002] [PMID: 30773423]
[8]
Agarwal, M.; Singh, V.; Sharma, S.C.; Sharma, P.; Ansari, Md. Y.; Jadav, S.S.; Yasmin, S.; Sreenivasulu, R.; Hassan, Md.H. Med. Chem. Res., 2016, 25, 2289-2303.
[http://dx.doi.org/10.1007/s00044-016-1672-1]
[9]
Spandana, Z.; Sreenivasulu, R.; Rekha, T.M.; Rao, M.V.B. Lett. Drug Des. Discov., 2019, 16, 656-662.
[http://dx.doi.org/10.2174/1570180816666181031125946]
[10]
Madhavi, S.; Sreenivasulu, R.; Raju, R.R. Monatsh. Chem., 2017, 148, 933-938.
[http://dx.doi.org/10.1007/s00706-016-1790-y]
[11]
Sreenivasulu, R.; Durgesh, R.; Jadav, S.S.; Sujitha, P.; Kumar, C.G.; Raju, R.R. Chem. Pap., 2018, 72, 1369-1378.
[http://dx.doi.org/10.1007/s11696-017-0372-8]
[12]
Subramanyam, M.; Sreenivasulu, R.; Rambabu, G.; Rao, M.V.B.; Rao, K.P. Lett. Drug Des. Discov., 2018, 15, 1299-1307.
[http://dx.doi.org/10.2174/1570180815666180219165119]
[13]
Ahsan, M.J.; Choudhary, K.; Jadav, S.S.; Yasmin, S.; Ansari, M.Y.; Sreenivasulu, R. Med. Chem. Res., 2015, 24, 4166-4180.
[http://dx.doi.org/10.1007/s00044-015-1457-y]
[14]
Madhavi, S.; Sreenivasulu, R.; Yazala, J.P.; Raju, R.R. Saudi Pharm. J., 2017, 25(2), 275-279.
[http://dx.doi.org/10.1016/j.jsps.2016.06.005] [PMID: 28344479]
[15]
Hatti, I.; Sreenivasulu, R.; Jadav, S.S.; Ahsan, M.J.; Raju, R.R. Monatsh. Chem., 2015, 146, 1699-1705.
[http://dx.doi.org/10.1007/s00706-015-1448-1]
[16]
Durgesh, R.; Sreenivasulu, R.; Pinapati, S.R.; Raju, R.R. J. Indian Chem. Soc., 2018, 95, 433-438.
[17]
Spandana, Z.; Sreenivasulu, R.; Rao, M.V.B. Lett. Org. Chem., 2019, 16, 662-667.
[http://dx.doi.org/10.2174/1570178616666181211094526]
[18]
Madhavi, S.; Sreenivasulu, R.; Ansari, Md. Y.; Ahsan, M.J.; Raju, R.R. Lett. Org. Chem., 2016, 13, 682-692.
[http://dx.doi.org/10.2174/1570178613666161021105317]
[19]
Sreenivasulu, R.; Sujitha, P.; Jadav, S.S.; Ahsan, M.J.; Kumar, C.G.; Raju, R.R. Monatsh. Chem., 2017, 148, 305-314.
[http://dx.doi.org/10.1007/s00706-016-1750-6]
[20]
Campaigne, E.; Knapp, D.R.; Neiss, E.S.; Bosin, T.R. Biologically active benzo (b)thiophene derivatives. Adv. Drug Res., 1970, 5, 1-54.
[PMID: 4395355]
[21]
Bosin, T.R.; Campaigne, E.E. Biologically active benzo [b]thiophene derivatives. II. Adv. Drug Res., 1977, 11, 191-232.
[PMID: 343525]
[22]
Sweidan, K.; Engelmann, J.; Rayyan, W.A.; Sabbah, D.; Zarga, M.A.; Sabbah, D.; Al-Qirim, T.; Al-Hiari, Y.; Sheikha, G.A.; Shattat, G. Lett. Drug Des. Discov., 2015, 12, 417-429.
[http://dx.doi.org/10.2174/1570180812666141201222527]
[23]
Martorana, A.; Gentile, C.; Perricone, U.; Piccionello, A.P.; Bartolotta, R.; Terenzi, A.; Pace, A.; Mingoia, F.; Almerico, A.M.; Lauria, A. Eur. J. Med. Chem., 2015, 90, 537-546.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.002] [PMID: 25486425]
[24]
Romagnoli, R.; Baraldi, P.G.; Carrion, M.D.; Lopez Cara, C.; Preti, D.; Fruttarolo, F.; Pavani, M.G.; Tabrizi, M.A.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Balzarini, J.; Hadfield, J.A.; Brancale, A.; Hamel, E. J. Med. Chem., 2007, 50(9), 2273-2277.
[http://dx.doi.org/10.1021/jm070050f] [PMID: 17419607]
[25]
Loidreau, Y.; Deau, E.; Marchand, P.; Nourrisson, M.R.; Logé, C.; Coadou, G.; Loaëc, N.; Meijer, L.; Besson, T. Eur. J. Med. Chem., 2015, 92, 124-134.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.038] [PMID: 25549552]
[26]
Wardakhan, W.W.; Abdel-Salam, O.M.; Elmegeed, G.A. Acta Pharm., 2008, 58(1), 1-14.
[http://dx.doi.org/10.2478/v10007-007-0041-5] [PMID: 18337204]
[27]
Radwan, M.A.A.; Shehab, M.A.; El-Shenawy, S.M. Monatsh. Chem., 2009, 140, 445-450.
[http://dx.doi.org/10.1007/s00706-008-0067-5]
[28]
Connor, D.T.; Cetenko, W.A.; Mullican, M.D.; Sorenson, R.J.; Unangst, P.C.; Weikert, R.J.; Adolphson, R.L.; Kennedy, J.A.; Thueson, D.O.; Wright, C.D.; Conroy, M.C. J. Med. Chem., 1992, 35(5), 958-965.
[http://dx.doi.org/10.1021/jm00083a023] [PMID: 1372359]
[29]
Moinet, G.; Leriche, C.; Kergoat, K. Antidiabetic compounds comprising benzofuran and benzothiophene derivatives EP1685121 A1.PCT/EP2004/012075,,
[30]
Zaher, A.F.; Khalil, N.A.; Ahmed, E.M. Orient. J. Chem., 2010, 26, 1241-1248.
[31]
Meyers, M.J.; Mnich, S.J.; Pierce, B.S.; Saabye, M.J.; Schindler, J.F.; South, S.A. Meyers, M.J.; Mnich, S.J.; Pierce, B.S.; Saabye, M.J.; Schindler, J.F.; South, S.A.; Webb, E.G.; Zhang, J.; Anderson, D.R. J. Pharmacol. Exp. Ther., 2010, 333(3), 797-807.
[http://dx.doi.org/10.1124/jpet.110.166173] [PMID: 20237073]
[32]
Kennedy, D.A.; Summers, L.A. J. Heterocycl. Chem., 1981, 18, 409-410.
[http://dx.doi.org/10.1002/jhet.5570180236]
[33]
Malamas, M.S.; Sredy, J.; Moxham, C.; Katz, A.; Xu, W.; McDevitt, R.; Adebayo, F.O.; Sawicki, D.R.; Seestaller, L.; Sullivan, D.; Taylor, J.R. J. Med. Chem., 2000, 43(7), 1293-1310.
[http://dx.doi.org/10.1021/jm990560c] [PMID: 10753467]
[34]
Niculescu-Duvaz, D.; Niculescu-Duvaz, I.; Suijkerbuijk, B.M.; Ménard, D.; Zambon, A.; Davies, L.; Pons, J.F.; Whittaker, S.; Marais, R.; Springer, C.J. Bioorg. Med. Chem., 2013, 21(5), 1284-1304.
[http://dx.doi.org/10.1016/j.bmc.2012.12.035] [PMID: 23376011]
[35]
Santillan, A.; McClure, K.J.; Allison, B.D.; Lord, B.; Boggs, J.D.; Morton, K.L.; Everson, A.M.; Nepomuceno, D.; Letavic, M.A.; Lee-Dutra, A.; Lovenberg, T.W.; Carruthers, N.I.; Grice, C.A. Bioorg. Med. Chem. Lett., 2010, 20(21), 6226-6230.
[http://dx.doi.org/10.1016/j.bmcl.2010.08.103] [PMID: 20843691]
[36]
Jones, C.D.; Jevnikar, M.G.; Pike, A.J.; Peters, M.K.; Black, L.J.; Thompson, A.R.; Falcone, J.F.; Clemens, J.A. J. Med. Chem., 1984, 27, 1057-1066.
[http://dx.doi.org/10.1021/jm00374a021] [PMID: 6431104]
[37]
Jordan, V.C. J. Med. Chem., 2003, 46(7), 1081-1111.
[http://dx.doi.org/10.1021/jm020450x] [PMID: 12646017]
[38]
Teresa, M.V.D.; Pinho, E.M. Curr. Org. Chem., 2005, 9, 925-958.
[http://dx.doi.org/10.2174/1385272054368420]
[39]
Li, W.T.; Hwang, D.R.; Chen, C.P.; Shen, C.W.; Huang, C.L.; Chen, T.W.; Lin, C.H.; Chang, Y.L.; Chang, Y.Y.; Lo, Y.K.; Tseng, H.Y.; Lin, C.C.; Song, J.S.; Chen, H.C.; Chen, S.J.; Wu, S.H.; Chen, C.T. J. Med. Chem., 2003, 46(9), 1706-1715.
[http://dx.doi.org/10.1021/jm020471r] [PMID: 12699388]
[40]
Frølund, B.; Jørgensen, A.T.; Tagmose, L.; Stensbøl, T.B.; Vestergaard, H.T.; Engblom, C.; Kristiansen, U.; Sanchez, C.; Krogsgaard-Larsen, P.; Liljefors, T. J. Med. Chem., 2002, 45(12), 2454-2468.
[http://dx.doi.org/10.1021/jm020027o] [PMID: 12036354]
[41]
Giovannoni, M.P.; Vergelli, C.; Ghelardini, C.; Galeotti, N.; Bartolini, A.; Dal Piaz, V. J. Med. Chem., 2003, 46(6), 1055-1059.
[http://dx.doi.org/10.1021/jm021057u] [PMID: 12620082]
[42]
Bhatt, A.H.; Parekh, H.H.; Pankh, A.R. Heterocycl. Commun., 1998, 4, 361-366.
[http://dx.doi.org/10.1515/HC.1998.4.4.361]
[43]
Talley, J.J.; Bertenshaw, S.R.; Brown, D.L.; Carter, J.S.; Graneto, M.J.; Kellogg, M.S.; Koboldt, C.M.; Yuan, J.; Zhang, Y.Y.; Seibert, K. J. Med. Chem., 2000, 43(9), 1661-1663.
[http://dx.doi.org/10.1021/jm000069h] [PMID: 10794682]
[44]
Ryng, S.; Sonnenberg, Z.; Zimecki, M. Arch. Immunol. Ther. Exp. (Warsz.), 2000, 48(2), 127-131.
[PMID: 10807054]
[45]
Zimecki, M.; Ryng, S.; Maczyński, M.; Chodaczek, G.; Kocieba, M.; Kuryszko, J.; Kaleta, K. Pharmacol. Rep., 2006, 58(2), 236-241.
[PMID: 16702626]
[46]
Mao, J.; Yuan, H.; Wang, Y.; Wan, B.; Pak, D.; He, R.; Franzblau, S.G. Bioorg. Med. Chem. Lett., 2010, 20(3), 1263-1268.
[http://dx.doi.org/10.1016/j.bmcl.2009.11.105] [PMID: 20022500]
[47]
Eccles, S.A.; Massey, A.; Raynaud, F.I.; Sharp, S.Y.; Box, G.; Valenti, M.; Patterson, L.; de Haven Brandon, A.; Gowan, S.; Boxall, F.; Aherne, W.; Rowlands, M.; Hayes, A.; Martins, V.; Urban, F.; Boxall, K.; Prodromou, C.; Pearl, L.; James, K.; Matthews, T.P.; Cheung, K.M.; Kalusa, A.; Jones, K.; McDonald, E.; Barril, X.; Brough, P.A.; Cansfield, J.E.; Dymock, B.; Drysdale, M.J.; Finch, H.; Howes, R.; Hubbard, R.E.; Surgenor, A.; Webb, P.; Wood, M.; Wright, L.; Workman, P. Cancer Res., 2008, 68(8), 2850-2860.
[http://dx.doi.org/10.1158/0008-5472.CAN-07-5256] [PMID: 18413753]

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