Skip to main content
Log in

Synthesis of some new thiazole derivatives and their cytotoxicity on different human tumor cell lines

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Some novel 1-(inden-3-ylidene)-2-(thiazol-2-ylidene)hydrazine derivatives 39 were synthesized by the Hantzsch reaction of thiosemicarbazone derivatives 2a2c with halo ketones and halo esters. Thiosemicarbazone derivatives reacted with hydrozonyl chlorides to give diazenyl-4-methylthiazole derivatives 11a11d. Structures of the products were elucidated from IR, 1H, and 13C NMR, and Mass spectra elucidate. The synthesized compounds were screened for their cytotoxicity against three human tumor cell lines. Twenty compounds showed high (≥60 %) antiproliferative activity over breast cancer (MCF-7). Compounds 2b, 3c, 4a, 4b, 6b, 6c, 7b, 8a, and 11b possessed higher cytotoxic activity over breast tumor cell line than Doxorubicin.

This is a preview of subscription content, log in via an institution to check access.

Access this article

We’re sorry, something doesn't seem to be working properly.

Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Similar content being viewed by others

References

  1. Siddiqui, N., Arshad, M.F., Ahsan, W., and Alam, M.S., Int. J. Pharm. Sci. Drug Res., 2009, vol. 1, p. 136.

    CAS  Google Scholar 

  2. Song, Y., Cornor, D.T., Sercel, A. D., Sorenson, R.J., Doubleday, R., Unangst, P.C., Roht, B.D., Beylin, V.G., Gilbertsen, R.B., Chan, K., Schrier, D.J., Guglietta, A., Bornemerier, D.A., and Dyer, R.D., J. Med. Chem., 1999, vol. 42, p. 1161. doi 10.1021/jm980570

    Article  CAS  Google Scholar 

  3. Abanauskas, L., Kalcas, V., Udrenaite, E., Gaidelis, P., Brukstus, A., and Dauksas, A., Pharmazie 2001, vol. 56, p. 617.

    Google Scholar 

  4. Medime, E. and Çapan, G., Il Farmaco, 1994, vol. 49, p. 449.

    Google Scholar 

  5. Chapleo, C.B., Myers, P.L., Smith, A.C., Stilling, M.R., Tulloch, I.F., and Walter, D.S., J. Med. Chem., 1988, vol. 31, p. 7. doi 1021/jm00396a004

    Article  CAS  Google Scholar 

  6. Chou, J.Y., Lai, S.H., Pan, S.L., Jow, G.M., Chern, J.W., and Guh, J.H., Biochem. Pharmacol., 2003, vol. 66, p. 115. doi 10.1016/s0006-2952(03)00254-5

    Article  CAS  Google Scholar 

  7. Mohamed, A.M., Al-Qalawi, H.R.M., El-Sayed, W.A., Arafa, W.A.A., Alhumaimess, M.S., and Hassan, A.K., Acta Polonia Pharm. Drug Res., 2015, vol. 72, no. 2, p. 307.

    CAS  Google Scholar 

  8. Mohamed, A.M., El-Sayed, W.A., Alsharari, M.A., Al-Qalawi, H.R.M., and Germoush, M.O., Arch. Pharm. Res., 2013, vol. 36, p. 1055. doi 10.1007/s12272-013-016-x

    Article  CAS  Google Scholar 

  9. Aly, A.A., Ramadan, M., Mohamed, A.M., and Eshak, E.A., J. Heterocycl. Chem., 2012, vol. 49, no. 5, p. 1009. doi 10.1002/jhet.843

    Article  CAS  Google Scholar 

  10. Mohamed, A.M., Amr, A.E., Alsharari, M.A., Al-Qalawi, H.R.M., Germoush, M.O., and Al-Omar, M.A., Am. J. Biochem. Biotechnol., 2011, vol. 7, no. 2, p. 43. doi 10.3844/ajbbsp.2011.43.54

    Article  CAS  Google Scholar 

  11. Rashad, A.E., El-Sayed, W.A., Mohamed, A.M., and Ali, M.M., Arch. Pharm.Chem. Life Sci., 2010, vol. 8, p. 440. doi 10.1002/ardp.201000002

    Article  Google Scholar 

  12. Amr, A.E., Mohamed, A.M., Mohamed, S.F., Abdel-Hafez, N.A., and Hammam, A.G., Bioorg Med. Chem., 2006, vol. 14, p. 5481. doi 10.1016/j.bmc.2006.04.045

    Article  CAS  Google Scholar 

  13. Hammam, A.G., Abd El-Salam, O.I., Mohamed, A.M., and Abdel-Hafez, N.A., Indian J. Chem. B, 2005, vol. 44, p. 1887. doi 10.1002/chin.200602131

    Google Scholar 

  14. Hammam, A.G., Fahmy, F.A.M., Amr, A.E., and Mohamd, A.M., Indian J. Chem. B, 2003, vol. 42, p. 1985. doi 10.1002/chin.200347130

    Google Scholar 

  15. Abd El-Salam, O.I., Hammam, A.G., and Abd El-Hafez, N.A., Egypt. J. Chem., 2006, vol. 49, no. 1, p. 63.

    Google Scholar 

  16. Farag, A.M., Mayhoub, A.S., Eldebss, T.M.A., Amr, A.E., Ali, K.A., Abdel-Hafez, N.A., and Abdulla, M.M., Arch. Pharm. Chem. Life Sci., 2010, vol. 343, p. 384. doi org/10.1016/j.ejmech.2010.09.054

    Article  CAS  Google Scholar 

  17. Farag, A.M., Ali, K.A., El-Debss, T.M.A., Mayhoub, A.S., Amr, A.E., Abdel-Hafez, N.A., and Abdulla, M.M., Eur. J. Med. Chem., 2010, vol. 45, p. 5887. doi org/10.101016/j.ejmech.2010.09.054

    Article  CAS  Google Scholar 

  18. Abdel-Hafez, N.A., Mohamed, S.F., El-Hag, F.A.A., Hawas, U.W., and Awad, H.M., Der Pharma Chemica, 2016, vol. 8, no. 14, p. 56.

    Google Scholar 

  19. Finkielsztein, L.M., Castro, E.F., Fabian, L.E., Moltrasio, G.Y., Campos, R.H., Cavallaro, L., and Moglioni, A.G., Eur. J. Med. Chem., 2008, vol. 43, p. 1767. doi org/10.1016/j.emech.2007.10.023

    Article  CAS  Google Scholar 

  20. Hegarty, A.F., Cashoman, M.P., and Scott, F.L. Chem. Commun., 1971, vol. 13, p. 884.

    Google Scholar 

  21. Thabrew, M., Hughes, R.D., Mcfarlane, I.G., J. Pharm. Pharmacol., 1997, vol. 49, no. 11, p. 1132. doi 10.1111/j.2042-7158.1997.tb06055.x

    Article  CAS  Google Scholar 

  22. Moustafa, S.M., Menshawi, B., Wassel, G.M., Mahmoud, K., and Mounier, M.M., Int. J. Chemtech. Res., 2014, vol. 6, no. 3, p. 1074.

    Google Scholar 

  23. Mosmann, T., J. Immunol Meth., 1983, vol. 65, no. 1, p. 55. doi 10.1016/0022-1759(83)90303-4

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. M. Mohamed.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohamed, A.M., Abdel-Hafez, N.A., Kassem, A.F. et al. Synthesis of some new thiazole derivatives and their cytotoxicity on different human tumor cell lines. Russ J Gen Chem 87, 2391–2400 (2017). https://doi.org/10.1134/S1070363217100218

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363217100218

Keywords

Navigation