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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 Anticancer Evaluation of Acetamides Comprising 1,2,3-triazole, 1,3,4-thiadiazole and Isothiazolo[4,3-b]pyridine Rings

Author(s): Shaik Shahinshavali, Nuthalapati Poojith, Venkat Rao Guttikonda, Reddymasu Sreenivasulu and Mandava Venkata Basaveswara Rao*

Volume 17, Issue 11, 2020

Page: [864 - 871] Pages: 8

DOI: 10.2174/1570178617666200225102939

Price: $65

Abstract

We have synthesized a library of new 1,2,3-triazole incorporated 1,3,4-thiadiazoleisothiazolo[ 4,3-b]pyridine derivatives 12a-j and have screened these products for their anticancer activities against four human cancer cell lines such as MCF-7 (breast cancer), A549 (lung cancer), DU-145 (prostate cancer), and MDA MB-231 (breast cancer) using MTT assay with etoposide as a positive control. Among them, compound 12e has shown excellent activities against MCF-7, A549, DU-145, and MDA-MB-231 with IC50 values of 0.53±0.055 μM, 0.18±0.077 μM, 0.10±0.082 μM, and 0.92±0.041 μM, respectively.

Keywords: 1, 2, 3-triazole, 1, 3, 4-thiadiazole, anticancer activity, azetepa, Carboxyamido triazole (CAI), isothiazolo[4, 3- b]pyridine.

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[1]
Eckhardt, S. Curr. Med. Chem. Anticancer Agents, 2002, 2(3), 419-439.
[http://dx.doi.org/10.2174/1568011024606389] [PMID: 12678741]
[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]
Vogelstein, B.; Kinzler, K.W. The Genetic Basis of Human Cancer; McGraw-Hill Education / Medical, 2005.
[4]
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]
[5]
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]
[6]
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]
[7]
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]
[8]
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]
[9]
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]
[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]
Agarwal, M.; Singh, V.; Sharma, S.K.; Sharma, P.; Ansari, M.Y.; Jadav, S.S.; Yasmin, S.; Sreenivasulu, R.; Hassan, M.Z.; Saini, V.; Ahsan, M. J. Med. Chem. Res., 2016, 25, 2289-2303.
[http://dx.doi.org/10.1007/s00044-016-1672-1]
[12]
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]
[13]
Madhavi, S.; Sreenivasulu, R. Ansari, Md. Lett. Org. Chem., 2016, 13, 682-692.
[http://dx.doi.org/10.2174/1570178613666161021105317]
[14]
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]
[15]
Subramanyam, M.; Sreenivasulu, R. Lett. Drug Des. Discov., 2018, 15, 1299-1307.
[http://dx.doi.org/10.2174/1570180815666180219165119]
[16]
Rudavath, D.; Sreenivasulu, R.; Pinapati, S.R.; Raju, R.R. J. Indian Chem. Soc., 2018, 95, 433-438.
[17]
Suma, V.R.; Sreenivasulu, R.; Subramanyam, M.; Rao, K.R.M. Russ. J. Gen. Chem., 2019, 89, 499-504.
[http://dx.doi.org/10.1134/S1070363219030228]
[18]
Shahinshavali, S.; Sreenivasulu, R.; Guttikonda, V.R.; Kolli, D.; Rao, M.V.B. Russ. J. Gen. Chem., 2019, 89, 324-329.
[http://dx.doi.org/10.1134/S1070363219020257]
[19]
Spandana, Z.; Sreenivasulu, R.; Rao, M.V.B. Lett. Org. Chem., 2019, 16, 662-667.
[http://dx.doi.org/10.2174/1570178616666181211094526]
[20]
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]
[21]
Devi, E.R.; Sreenivasulu, R.; Rao, K.P.; Nadh, R.V.; Sireesha, M. Lett. Org. Chem., 2020, 17, 54-60.
[http://dx.doi.org/10.2174/1570178616666190528095548]
[22]
Reddy, K.T.; Sreenivasulu, R.; Raju, R.R. J. Indian Chem. Soc., 2019, 96, 1085-1090.
[23]
Murthy, I.S.; Sreenivasulu, R.; Alluraiah, G.; Raju, R.R. Russ. J. Gen. Chem., 2019, 89, 1718-1723.
[http://dx.doi.org/10.1134/S1070363219080279]
[24]
Rao, B.V.D.; Sreenivasulu, R.; Rao, M.V.B. Russ. J. Gen. Chem., 2019, 89, 2115-2120.
[http://dx.doi.org/10.1134/S1070363219100207]
[25]
Yakantham, T.; Sreenivasluu, R.; Raju, R.R. Russ. J. Gen. Chem., 2019, 89, 1485-1490.
[http://dx.doi.org/10.1134/S1070363219070181]
[26]
Sayed, A.R. Tetrahedron, 2012, 68, 2784-2789.
[http://dx.doi.org/10.1016/j.tet.2012.02.011]
[27]
Shahcheragh, S.M.; Habibi, A.; Khosravi, S. Tetrahedron Lett., 2017, 58, 855-859.
[http://dx.doi.org/10.1016/j.tetlet.2017.01.057]
[28]
Luo, Z.; Chen, B.; He, S.; Shi, Y.; Liu, Y.; Li, C. Bioorg. Med. Chem. Lett., 2012, 22(9), 3191-3193.
[http://dx.doi.org/10.1016/j.bmcl.2012.03.043] [PMID: 22483583]
[29]
Aliabadi, A.; Eghbalian, E.; Kiani, A. Iran. J. Basic Med. Sci., 2013, 16(11), 1133-1138.
[PMID: 24494064]
[30]
Poorrajab, F.; Ardestani, S.K.; Emami, S.; Behrouzi-Fardmoghadam, M.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem., 2009, 44, 1758-1762.
[http://dx.doi.org/10.1016/j.ejmech.2008.03.039] [PMID: 18485538 ]
[31]
Gupta, J.K.; Yadav, R.K.; Dudhe, R.; Sharma, P.K. Int. J. Pharm. Tech. Res., 2010, 2, 1493-1507.
[32]
Li, P.; Shi, L.; Gao, M-N.; Yang, X.; Xue, W.; Jin, L-H.; Hu, D.Y.; Song, B.A. Bioorg. Med. Chem. Lett., 2015, 25(3), 481-484.
[http://dx.doi.org/10.1016/j.bmcl.2014.12.038] [PMID: 25563889 ]
[33]
Gür, M.; Muglu, H.; Çavus, M.S.; Güder, A.; Sayiner, H.S.; Kandemirli, F. J. Mol. Struct., 2017, 1134, 40-50.
[http://dx.doi.org/10.1016/j.molstruc.2016.12.041]
[34]
Chen, Z.; Xu, W.; Liu, K.; Yang, S.; Fan, H. Molecules, 2010, 15, 9046-9056.
[http://dx.doi.org/10.3390/molecules15129046] [PMID: 21150824]
[35]
Kaur, H.; Kumar, S.; Vishwakarma, P.; Sharma, M.; Saxena, K.K.; Kumar, A. Eur. J. Med. Chem., 2010, 45(7), 2777-2783.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.060] [PMID: 20392546 ]
[36]
Hafez, H.N.; Hegab, M.I.; Ahmed-Farag, I.S.; El-Gazzar, A.B.A. Bioorg. Med. Chem., 2008, 18, 4538-4543.
[http://dx.doi.org/10.1016/j.bmcl.2008.07.042]
[37]
Turner, S.; Myers, M.; Gadie, B.; Nelson, A.J.; Pape, R.; Saville, J.F.; Doxey, J.C.; Berridge, T.L. J. Med. Chem., 1988, 31, 902-906.
[http://dx.doi.org/10.1021/jm00400a003] [PMID: 3361578]
[38]
Ragab, F.A.; Heiba, H.I.; El-Gazzar, M.G.; Abou-Seri, S.M.; El-Sabbagh, W.A.; El-Hazek, R.M. J. Photochem. Photobiol. B, 2017, 166, 285-300.
[http://dx.doi.org/10.1016/j.jphotobiol.2016.12.007] [PMID: 28013183]
[39]
El-Gohary, N.S.; Shaaban, M.I. Eur. J. Med. Chem., 2013, 63, 185-195.
[http://dx.doi.org/10.1016/j.ejmech.2013.02.010] [PMID: 23474904]
[40]
Balaji, K.; Bhatt, P.; Mallika, D.; Jha, A. Int. J. Pharm. Pharm. Sci., 2015, 7, 145-149.
[41]
Pattan, S.R.; Kekare, P.; Dighe, N.S.; Nirmal, S.A.; Musmade, D.S.; Parjane, S.K.; Daithankar, A.V. J. Chem. Pharm. Res., 2009, 1, 191-198.
[42]
Choy, D.S.; Arandia, J.; Rosenbaum, I. Int. J. Cancer, 1967, 2(2), 189-193.
[http://dx.doi.org/10.1002/ijc.2910020213] [PMID: 6039768]
[43]
Dalvie, D.K.; Kalgutkar, A.S.; Khojasteh-Bakht, S.C.; Obach, R.S.; O’Donnell, J.P. Chem. Res. Toxicol., 2002, 15(3), 269-299.
[http://dx.doi.org/10.1021/tx015574b] [PMID: 11896674]
[44]
Horne, W.S.; Yadav, M.K.; Stout, C.D.; Ghadiri, M.R. J. Am. Chem. Soc., 2004, 126(47), 15366-15367.
[http://dx.doi.org/10.1021/ja0450408] [PMID: 15563148]
[45]
Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem. Int. Ed., 2001, 40, 2004-2021.
[http://dx.doi.org/10.1002/1521-3773(20010601)40:11<2004:AID-ANIE2004>3.0.CO;2-5]
[46]
Kolb, H.C.; Sharpless, K.B. Drug Discov. Today, 2003, 8(24), 1128-1137.
[http://dx.doi.org/10.1016/S1359-6446(03)02933-7] [PMID: 14678739]
[47]
Cho, S.; Oh, S.; Um, Y.; Jung, J-H.; Ham, J.; Shin, W-S.; Lee, S. Bioorg. Med. Chem. Lett., 2009, 19(2), 382-385.
[http://dx.doi.org/10.1016/j.bmcl.2008.11.067] [PMID: 19081249]
[48]
Al-Masoudi, N.A.; Al-Soud, Y.A. Tetrahedron Lett., 2002, 43, 4021-4022.
[http://dx.doi.org/10.1016/S0040-4039(02)00733-5]
[49]
Kumar, K.K.; Seenivasan, S.P.; Kumar, V.; Das, T.M. Carbohydr. Res., 2011, 346, 2084-2090.
[http://dx.doi.org/10.1016/j.carres.2011.06.028] [PMID: 21767828]
[50]
Lal, K.; Kaushik, C.P.; Kumar, A. Med. Chem. Res., 2015, 24, 3258-3271.
[http://dx.doi.org/10.1007/s00044-015-1378-9]
[51]
da Silva, F.C.; de Souza, M.C.B.V.; Frugulhetti, I.I.P.; Castro, H.C.; Souza, S.L.O.; de Souza, T.M.L.; Rodrigues, D.Q.; Souza, A.M.T.; Abreu, P.A.; Passamani, F.; Rodrigues, C.R.; Ferreira, V.F. Eur. J. Med. Chem., 2009, 44, 373-383.
[http://dx.doi.org/10.1016/j.ejmech.2008.02.047] [PMID: 18486994 ]
[52]
Costa, M.S.; Boechat, N.; Rangel, E.A. da Silva, Fde.C.; de Souza, A.M.T.; Rodrigues, C.R.; Castro, H.C.; Junior, I.N.; Lourenço, M.C.S.; Wardell, S.M.S.V.; Ferreira, V.F. Bioorg. Med. Chem., 2006, 14(24), 8644-8653.
[http://dx.doi.org/10.1016/j.bmc.2006.08.019] [PMID: 16949290]
[53]
Kumar, K.; Pradines, B.; Madamet, M.; Amalvict, R.; Kumar, V. Eur. J. Med. Chem., 2014, 86, 113-121.
[http://dx.doi.org/10.1016/j.ejmech.2014.08.053] [PMID: 25147153]
[54]
Bokor, E.; Docsa, T.; Gergely, P.; Somsák, L. Bioorg. Med. Chem., 2010, 18(3), 1171-1180.
[http://dx.doi.org/10.1016/j.bmc.2009.12.043] [PMID: 20080412]
[55]
Biagi, G.; Dell’Omodarme, G.; Ferretti, M.; Giorgi, I.; Livi, O.; Scartoni, V.; Tiscione, E. Farmaco, 1990, 45(11), 1181-1192.
[PMID: 2128450]
[56]
Ferreira, S.B.; Sodero, A.C.R.; Cardoso, M.F.C.; Lima, E.S.; Kaiser, C.R.; Silva, F.P., Jr; Ferreira, V.F. J. Med. Chem., 2010, 53(6), 2364-2375.
[http://dx.doi.org/10.1021/jm901265h] [PMID: 20170190]
[57]
Cunha, A.C.; Figueiredo, J.M.; Tributino, J.L.M.; Miranda, A.L.P.; Castro, H.C.; Zingali, R.B.; Fraga, C.A.M.; de Souza, M.C.B.V.; Ferreira, V.F.; Barreiro, E.J. Bioorg. Med. Chem, 2003, 11, 2051-2059.
[http://dx.doi.org/10.1016/S0968-0896(03)00055-5] [PMID: 12670656]
[58]
Felder, C.C.; Ma, A.L.; Liotta, L.A.; Kohn, E.C. J. Pharmacol. Exp. Ther., 1991, 257(3), 967-971.
[PMID: 1646332]
[59]
Kohn, E.C.; Sandeen, M.A.; Liotta, L.A. Cancer Res., 1992, 52(11), 3208-3212.
[PMID: 1591730]
[60]
Wasilenko, W.J.; Palad, A.J.; Somers, K.D.; Blackmore, P.F.; Kohn, E.C.; Rhim, J.S.; Wright, G.L., Jr; Schellhammer, P.F. Int. J. Cancer, 1996, 68(2), 259-264.
[http://dx.doi.org/10.1002/(SICI)1097-0215(19961009)68:2<259:: AID-IJC20>3.0.CO;2-4] [PMID: 8900438]
[61]
Berrie, A.H.; Newbold, G.T.; Spring, F.S. J. Chem. Soc., 1952, 2042-2046.
[http://dx.doi.org/10.1039/jr9520002042]
[62]
Kovackova, S.; Chang, L.; Bekerman, E.; Neveu, G.; Barouch-Bentov, R.; Chaikuad, A.; Heroven, C.; Šála, M.; De Jonghe, S.; Knapp, S.; Einav, S.; Herdewijn, P. J. Med. Chem., 2015, 58(8), 3393-3410.
[http://dx.doi.org/10.1021/jm501759m] [PMID: 25822739]
[63]
Rao, V.R.; Srinivasan, V.R. Indian J. Chem., 1970, 8, 509-513.

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