Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 2, pp 348–356 | Cite as

Synthesis of New 1,3,4-Oxadiazole-benzimidazole Derivatives as Potential Antioxidants and Breast Cancer Inhibitors with Apoptosis Inducing Activity

  • E. A. Abd El-MeguidEmail author
  • H. M. Awad
  • M. M. Anwar
Article
  • 18 Downloads

Abstract

Synthesis of new compounds combining benzimidazole with 1,3,4-oxadiazole functionalized by various alkyl and heterocyclic moieties is studied. The new hybrids were evaluated as DPPH radical scavengers and antioxidants. The most active compounds 1, 2, 3a, 3c, and 5d were tested as anticancer agents against MCF-7 and MDA-MB-231 breast cancer cells. The biological study demonstrated significant sensitivity of both types of cancer cells towards the synthesized compounds in comparison with erlotinib used as a reference drug. Cell cycle and apoptosis analysis indicated compound 5d as the one inducing G2/M phase arrest and apoptosis in MCF-7 and MDA-MB-231 cancer cells, in addition to its upregulation of caspases-3 and caspases-9.

Keywords

oxadiazole-benzimidazole antioxidant activity breast cancer apoptotic effect 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Abd El-Karim, S.S., Anwar, M.M., Zaki, E.R., Elseginy, S.A., and Nofal, Z.M., Future Med. Chem., 2018, vol. 10(2), p. 157. doi 10.4155/fmc-2017-0137Google Scholar
  2. 2.
    Abd El-Meguid, E.A. and Ali, M.M., Res. J. Pharm. Biol. Chem. Sci. (RJPBCS), 2015, vol. 6(2), p. 524.Google Scholar
  3. 3.
    Munde, M., Lee, M., Neidle, S., Arafa R., Boykin, D.W., Liu, Y., Bailly, C., and Wilson, W.D., J. Am. Chem. Soc., 2007, vol. 129, p. 5688. doi 10.1021/ja069003nCrossRefGoogle Scholar
  4. 4.
    Wilson, W.D., Nguyen, B., Tanious, F.A., Mathis, A., Hall, J.E., Stephens, C.E., and Boykin, D.W., Curr. Med. Chem. Anticancer Agents, 2005, vol. 5, p. 389.CrossRefGoogle Scholar
  5. 5.
    Bistrovi, A., Krstulovi, L., Harej, A., Grbčić, P., Sedić, M., Koštrun, S., Kraljević, S., Miroslav, P., Silvana, B., and Malić, S.,, Eur. J. Med. Chem., 2018, vol. 143, p. 1616. 10.1016/j.ejmech.2017.10.061CrossRefGoogle Scholar
  6. 6.
    Almasirad, A., Mousavi, Z., Tajik, M., Assarzadeh, M.J., and Shafiee A., DARU J. Pharm. Sci., 2014, vol. 22(1), p. 22.Google Scholar
  7. 7.
    Pokhodylo, N., Shyyka, O., and Matiychuk, V., Sci. Pharm. 2013, vol. 81(3), p. 663. doi 10.3797/scipharm.1307-09Google Scholar
  8. 8.
    Dua, Q-R., Lia, D-D., and Pia, Y-Z., Bioorg. Med. Chem., 2013, vol. 21(8), p. 2286. doi 10.1016/j.bmc.2013.02.008Google Scholar
  9. 9.
    Shingare, R.M., Patil, Y.S., Sangshetti, J.N., Patil, R.B., Rajani, D.P. and Madje, B.R., Med. Chem. Res., 2018, vol. 27(4), p. 1283. doi 10.1007/s00044-018-2148-2Google Scholar
  10. 10.
    Nasr, T., Bondock, S., Rashed, H.M., Fayad, W., Youns, M., and Sakr, T.M., Eur. J. Med. Chem., 2018, vol. 151, p. 723. doi 10.1016/j.ejmech.2018.04.014CrossRefGoogle Scholar
  11. 11.
    Nasr, T., Bondock, S., and Youns, M., Eur. J. Med. Chem., 2014, vol. 76, p. 539. doi 10.1016/j.ejmech.2014.02.026CrossRefGoogle Scholar
  12. 12.
    Garuti, L., Roberti, M., and Bottegoni, G., Curr. Med. Chem., 2014, vol. 21, p. 2284. doi 10.2174/0929867321666140217105714CrossRefGoogle Scholar
  13. 13.
    Akhtar, W., Khan, M.F., Verma, G., Shaquiquzzaman, G.M., Rizvi, M.A., Mehdi, S.H., Akhter, M., and Alam, M.M., Eur. J. Med. Chem., 2017, vol. 126, p. 705. doi 10.1016/j.ejmech.2014.02.026CrossRefGoogle Scholar
  14. 14.
    Akhtar, M.J., Siddiqui, A.A., Khan, A.A., Ali, Z., Dewangan, R.P., Pasha, S. and Yar, M.S. Eur. J. Med. Chem., 2017, vol. 126, p. 853. doi 10.1016/j.ejmech.2016.12.014CrossRefGoogle Scholar
  15. 15.
    Menteşe, E., Yılmaz, F., Baltaş, N., Bekircan, O., and Kahveci, B., J. Enzyme Inhib. Med. Chem., 2015, vol. 30(3), p. 435. doi 10.3109/14756366.2014.943203Google Scholar
  16. 16.
    Abd El-Meguid, E.A., Kotb, E.R., and Mohamed, S.F., Int. J. Pharm. Tech., 2015, vol. 7(1), p. 8363.Google Scholar
  17. 17.
    Abd El-Meguid, E.A., Int. J. Pharm. Tech., 2015, vol. 7(3), p. 10014.Google Scholar
  18. 18.
    Abd El-Meguid, E.A. and Ali, M.M., Res. Chem. Intermed., 2016, vol. 42(2), p. 1521. doi 10.1007/s11164-015-2100-8Google Scholar
  19. 19.
    Mohamed, S.F., Kotb, E.R., Abd El-Meguid, E.A., and Awad, H.M., Res. Chem. Intermed., 2017, vol. 43(1), p. 437. doi 10.1007/s11164-016-2633-5Google Scholar
  20. 20.
    Abd El-Meguid, E.A., Egypt. Pharm. J., 2014, vol. 13, p. 113. doi 10.4103/1687-4315.147072CrossRefGoogle Scholar
  21. 21.
    Hamdy, N.A., Anwar, M.M., Abu-Zied K.M., and Awad, H.M., Acta Poloniae Pharm. Drug Res., 2013, vol. 70(6), p. 987.Google Scholar
  22. 22.
    Diab, S., Teo, T., Kumarasiri, M., Lim, P., Yu, M., Lam, F., Basnet, S K.C., Sykes, M.J., Albrecht, H., and Wang, S.,, Chem. Med. Chem., 2014, vol. 9, p. 962. doi 10.1002/cmdc.201490016CrossRefGoogle Scholar
  23. 23.
    Thornton, T.M. and Rincon, M., Int. J. Biol. Sci., 2009, vol. 5(1), p. 44.Google Scholar
  24. 24.
    van Raam, B.J. and Salvesen, G.S., Handbook of Proteolytic Enzymes, 3rd ed., 2013, vol. 2, p. 2252.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • E. A. Abd El-Meguid
    • 1
    Email author
  • H. M. Awad
    • 2
  • M. M. Anwar
    • 3
  1. 1.Department of Chemistry of Natural and Microbial ProductsNational Research CentreDokki, CairoEgypt
  2. 2.Department of Tanning Materials and Leather TechnologyNational Research CentreDokki, CairoEgypt
  3. 3.Department of Therapeutic ChemistryNational Research CentreDokki, CairoEgypt

Personalised recommendations