Synthesis and Anticancer Activity of (E)-5-[(1-Aryl-1H-1,2,3-triazol-4-yl)methylene]thiazolidine-2,4-diones


A novel series of 1,2,3-triazolylthiazolidinedione analogs have been synthesized by the condensation of the corresponding 1-aryl-1H-1,2,3-triazole-4-carbaldehydes with thiazolidine-2,4-dione in the presence of KOH. The title compounds were evaluated for their in vitro anticancer activity using MTT assay against four cancer cell lines: A549 (lung), HT-29 (colon), MCF-7 (breast), and A375 (melanoma). Most compounds displayed good anticancer activity, but hydroxy- and nitro-substituted derivatives showed higher activity than the others.

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  1. 1

    Arshad, M., Shoeb Khan, M., Asghar Nami, S.A., and Ahmad, D., Russ. J. Gen. Chem., 2018, vol. 88, p. 2154.

    CAS  Article  Google Scholar 

  2. 2

    Terzioglu, N., Karali, N., Gursoy, A., Pannecouque, C., Leysen, P., Paeshuyse, J., Neyts, J., and Clercq, E., Arkivoc, 2006, vol. x, p. 109.

  3. 3

    Sohda, T., Mizuno, K., Tawada, H., Sugiyama, Y., Fugita, T., and Kawamatsu, Y., Chem. Pharm. Bull., 1982, vol. 30, p. 3563.

    CAS  Article  PubMed  Google Scholar 

  4. 4

    Goel, B., Ram, T., Tyagi, R., Bansal, E., Kumar, A., Mukherjee, D., and Sinha, J.N., Eur. J. Med. Chem., 1999, vol. 34, p. 265.

    CAS  Article  Google Scholar 

  5. 5

    Sharma, R.K., Younis, Y., Mugumbate, G., Njoroge, M., Gut, J., Rosenthal, P.J., and Chibale, K., Eur. J. Med. Chem., 2015, vol. 90, p. 507.

    CAS  Article  PubMed  Google Scholar 

  6. 6

    Balzarini, J., Orzeszko, B, Maurin, J.K., and Orzeszko, A., Eur. J. Med. Chem., 2007, vol. 42, p. 993.

    CAS  Article  PubMed  Google Scholar 

  7. 7

    Fathy, U., Gouhar, R.S., Awad, H.M., and Abdel-Aziz, H.A., Russ. J. Gen. Chem., 2017, vol. 87, p. 2951.

    CAS  Article  Google Scholar 

  8. 8

    Mizzoni, R.H. and Eisman, P.C., J. Am. Chem. Soc., 1957, vol. 80, p. 3471.

    Article  Google Scholar 

  9. 9

    Ottana, R., Maccari, R., Giglio, M., Del Corso, A., Cappiello, M., Mura, U., Cosconati, S., Marinelli, L., Novellino, E., Sartini, S., La Motta, C., and Da Settimo, F., Eur. J. Chem., 2011, vol. 46, p. 2797.

    CAS  Article  Google Scholar 

  10. 10

    Ashok, D., Ganesh, A., Vijaya Lakshmi, B., Ravi, S., and Ramesh, B., Org. Commun., 2014, vol. 8, p. 24.

    Google Scholar 

  11. 11

    Ashok, D., Ravi, S., Ganesh, A., and Vijaya Lakshmi, B., Med. Chem. Res., 2016, vol. 25, p. 909.

    CAS  Article  Google Scholar 

  12. 12

    Ming-Xia, S. and Xian-Qing, D., J. Enz. Inhibition Med. Chem., 2018, vol. 33, p. 1453.

    CAS  Article  Google Scholar 

  13. 13

    Kumar, A., Sathish Kumar, B., Sreenivas, E., and Subbaiah, T., Russ. J. Gen. Chem., 2018, vol. 88, p. 587.

    CAS  Article  Google Scholar 

  14. 14

    Lazrek, H.B., Taourirte, M., Oulih, T., Barascut, J.L., Imbach, JL., Pannecouque, C., Witrouw, M., and De Clercq, E., Nucleosides Nucleotides Nucleic Acids, 2001, vol. 20, p. 1949.

    CAS  Article  PubMed  Google Scholar 

  15. 15

    Mubarak, H.S., Dnyaneshwar, D.S., Laxman, N.D., Sarkar, F., Kalam Khan, A., Jaiprakash, N.S., and Bapurao, B.S., Med. Chem. Commun., 2015, vol. 6, p. 1104.

    Article  Google Scholar 

  16. 16

    Mounika, P., Aishwarya, M.N.L., Pranabesh, S., Prathima, S., and Niranajan, B.M., Asian J. Pharm. Res., 2017, vol. 7, p. 124.

    Article  Google Scholar 

  17. 17

    Shahnaz, Md., Bhai, P.K., and Bhai, R., J. Drug Deliv. Ther., 2013, vol. 3, p. 96.

    CAS  Article  Google Scholar 

  18. 18

    Bahare, R.S. and Kulkarni, V.M., Der Pharma Chem., 2011, vol. 3, p. 164.

    Google Scholar 

  19. 19

    Boechat, N., Ferreira, V.F., Ferreira, S.B., de Lourdes, G., Ferreira, M., de, C., da Silva, F., Bastos, M.M., Dos, S., Costa, M., Lourenço, M.C., Pinto, A.C., Krettli, A.U., Aguiar, A.C., Teixeira, B.M., da Silva, N.V., Martins, P.R., Bezerra, F.A., Camilo, A.L., da Silva, G.P., and Costa, C.C., J. Med. Chem., 2011, vol. 54, p. 5988.

    CAS  Article  PubMed  Google Scholar 

  20. 20

    Aliabadi, A., Shamsa, F., Ostad, S.N., Emami, S., Shafiee, A., Davoodi, J., and Foroumadi, A., Eur. J. Med. Chem., 2010, vol. 11, p. 5384.

    CAS  Article  Google Scholar 

  21. 21

    Bilge, B., Serda, K.G., Yagmur, K., Aysen, E.O., and Sevim, A., Bilge Int. J. Sci. Technol. Res., 2019, vol. 3, p. 1.

    Article  Google Scholar 

  22. 22

    Degorce, S.L., Barlaam, B., Cadogan, E., Dishington, A.P., Ducray, R., Glossop, S.C., Hassall, L.A., Lach, F., Lau, A., Mcguire, T.M., Nowak, T., Ouvry, G., Pike, K.G., and Thomason, A.G., J. Med. Chem., 2016, vol. 59, p. 6281.

    CAS  Article  PubMed  Google Scholar 

  23. 23

    Hassanin, H.M., Serya, R.A.T., Abd Elmoneam, W.R., and Mostafa, M.A., R. Soc. Open Sci., 2018, vol. 5, p. 172407.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

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The authors are grateful to the Department of Science of Humanities, Vignan’s Foundation for Science Technology and Research (VFSTR) University, for providing laboratory facilities.

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Correspondence to V. K. Manikala.

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Manikala, V.K., Rao, V.M. Synthesis and Anticancer Activity of (E)-5-[(1-Aryl-1H-1,2,3-triazol-4-yl)methylene]thiazolidine-2,4-diones. Russ J Org Chem 56, 863–868 (2020).

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  • thiazolidinediones
  • 1,2,3-triazole
  • anticancer activity
  • molecular docking studies