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Synthesis and biological evaluation of 3-(2,4-dichlorophenoxymethyl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents

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Abstract

Series of novel 3-(2,4-dichlorophenoxymethyl)-1-phenyl-1H-pyrazole derivatives with various substituents at positions 4 and 5 were synthesized. Antitumor activity of all the synthesized compounds was evaluated by using SRB assay on four cell lines: lung carcinoma (A549), human hepatocellular carcinoma (HepG2), colon carcinoma (HCT116) and mammary gland breast cancer (MCF-7) cell lines. Some of the synthesized compounds showed promising activity in comparison with doxorubicin against lung carcinoma cell lines. Incorporating arylidene moiety at position-4 in pyrazole ring improved and displayed strong effect on the cytotoxic activity. Compound 9c incorporating 4-chlorophenyl moiety was the most potent toward all tested cell lines.

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References

  1. A.A. Farag, M.F. El Shehry, S.Y. Abbas, S.N. Abd-Alrahman, A.A. Atrees, H.Z. Al-basheer, Y.A. Ammar, Z. Naturforsch. B 70, 519–526 (2015)

    Article  CAS  Google Scholar 

  2. M.F. Khan, M.M. Alam, G. Verma, W. Akhtar, M. Akhter, M. Shaquiquzzaman, Eur. J. Med. Chem. 120, 170–201 (2016)

    Article  CAS  Google Scholar 

  3. S. Ganguly, S.K. Jacob, Mini Rev. Med. Chem. 17, 959–983 (2017)

    Article  CAS  Google Scholar 

  4. S. Küçükgüzel, S. Senkardes, Eur. J. Med. Chem. 97, 786–815 (2015)

    Article  Google Scholar 

  5. I. Desai, K. Sinha, W. Null, M.A. Wolter, T. Suckow, S. King, R. Amin, Sinha. Int. J. Cancer 127, 230–238 (2010)

    Article  CAS  Google Scholar 

  6. P. Sooriakumaran, S.E. Langley, R.W. Laing, H.M. Coley, J. Chemother. 19, 21–32 (2007)

    Article  CAS  Google Scholar 

  7. M.F. El Shehry, M.M. Ghorab, S.Y. Abbas, E.A. Fayed, S.A. Shedid, Y.A. Ammar, Eur. J. Med. Chem. 143, 1463–1473 (2018)

    Article  Google Scholar 

  8. E.A.E. El-Helw, M.M. Gado, A.K. El-Ziaty, J. Iran. Chem. Soc. 17, 1479–1492 (2020)

    Article  CAS  Google Scholar 

  9. J.C. Jung, E.B. Watkins, M.A. Avery, Tetrahedron 58, 3639–3646 (2002)

    Article  CAS  Google Scholar 

  10. J. Pernak, A. Syguda, K. Materna, E. Janus, P. Kardasz, T. Praczyk, Tetrahedron 68, 4267–4273 (2012)

    Article  CAS  Google Scholar 

  11. S.Y. Abbas, K.A.M. El-Bayouki, W.M. Basyouni, E.A. Mostafa, Med. Chem. Res. 27, 571–582 (2018)

    Article  CAS  Google Scholar 

  12. S.Y. Abbas, A.A. Farag, Y.A. Ammar, A.A. Atrees, A.F. Mohamed, A.A. El-Henawy, Monatsh. Chem. 144, 1725–1733 (2013)

    Article  CAS  Google Scholar 

  13. R.A.K. Al-Harbi, M.A.M.S. El-Sharief, S.Y. Abbas, Bioorg. Chem. 90, 103088 (2019)

    Article  CAS  Google Scholar 

  14. S.Y. Abbas, R.A.K. Al-Harbib, M.A.M.S. El-Sharief, Eur. J. Med. Chem. 198, 112363 (2020)

    Article  CAS  Google Scholar 

  15. E.M. El-Telbani, M.F. El Shehry, G.A.M. Nawwar, Monatsh. Chem. 139, 685–689 (2008)

    Article  CAS  Google Scholar 

  16. P. Skehan, R. Storeng, D. Scudiero, A. Monks, M.J. Mahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenny, M.R. Boyd, J. Nat. Cancer Inst. 82, 1107–1112 (1990)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Pesticide Chemistry Department, National Research Centre, Cairo, 12622, Egypt

    Mohamed F. El Shehry

  2. Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, Egypt

    Samir Y. Abbas

  3. Pharmaceutical Chemistry Department, Faculty of Pharmacy (Girls), Al-Azher University, Nasr City, Cairo, Egypt

    Amel M. Farrag

  4. Chemistry Department, Faculty of Science, Al-Azhar University (Girls), Cairo, Egypt

    Sawsan A. Fouad

  5. Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, Egypt

    Yousry A. Ammar

Authors
  1. Mohamed F. El Shehry
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  2. Samir Y. Abbas
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  3. Amel M. Farrag
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  4. Sawsan A. Fouad
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  5. Yousry A. Ammar
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Corresponding authors

Correspondence to Samir Y. Abbas or Yousry A. Ammar.

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El Shehry, M.F., Abbas, S.Y., Farrag, A.M. et al. Synthesis and biological evaluation of 3-(2,4-dichlorophenoxymethyl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents. J IRAN CHEM SOC 17, 2567–2575 (2020). https://doi.org/10.1007/s13738-020-01951-w

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  • DOI: https://doi.org/10.1007/s13738-020-01951-w

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