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Cytotoxic activity and density functional theory studies of some 1,3-diphenylpyrazolyltetrahydropyrimidine derivatives

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Abstract

Proclivity of tetrahydropyrimidinethione derivative encompassing 1,3-diphenylpyrazole moiety 1 was studied toward some carbon electrophiles in an attempt to synthesize some heteroannulated compounds. Also, pyrimidine dimer and pyrimidinotriazepine derivative were obtained through reactions with 1,2-diaminoethane and 2-cyanoacetohydrazide, respectively. Oxidation of the starting pyrimidinethione 2 was mainly dependent on the oxidizing agent used. The newly synthesized compounds were characterized by their analytical and spectral data including IR, 1H NMR, 13C NMR and mass spectral data. The synthesized compounds were examined as antitumor agents against four human different cancer cell lines including hepatocellular carcinoma (HePG2), breast adenocarcinoma (MCF7), prostate cancer (PC3) and colon cancer (HCT-116). The results obtained revealed that some of them exhibited satisfactory activities.

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References

  1. G. Maga, M. Radi, M.A. Gerard, M. Botta, E. Ennifar, Viruses 2, 880 (2010)

    Article  CAS  Google Scholar 

  2. M.B. Deshmukh, S.M. Salunkhe, D.R. Patil, P.V. Anbhule, Eur. J. Med. Chem. 2009(44), 2651 (2009)

    Article  Google Scholar 

  3. B.R. Prashantha Kumar, G. Sankar, R.B. Nasir Baig, S. Chandrashekaran, Eur. J. Med. Chem. 44, 4192 (2009)

    Article  CAS  Google Scholar 

  4. K.V. Sujith, J.N. Rao, P. Shetty, B. Kalluraya, Eur. J. Med. Chem. 44, 3697 (2009)

    Article  CAS  Google Scholar 

  5. A.M. Isloor, B. Kalluraya, P. Shetty, Eur. J. Med. Chem. 44, 3784 (2009)

    Article  CAS  Google Scholar 

  6. M. Larhed, A. Hallberg, Drug Discov. Today 6(8), 406 (2001)

    Article  CAS  Google Scholar 

  7. T.P. Selby, G.P. Lahm, T.M. Stevenson, K.A. Hughes, D. Cordova, I.B. Annan, Bioorg. Med. Chem. Lett. 23, 6341 (2013)

    Article  CAS  Google Scholar 

  8. H. Yu, M. Xu, Y. Cheng, H. Wu, Y. Luo, B. Li, Arkivoc 6, 26 (2012)

    Google Scholar 

  9. P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57(51), 9225 (2001)

    Article  Google Scholar 

  10. P. Callery, P. Gannett, Cancer and cancer chemotherapy, in Foye’s Principles of Medicinal Chemistry, 5th edn., ed. by D.A. Williams, T.L. Lemke (Lippincot Williams and Wilkins, Philadelphia, 2002), p. 934

    Google Scholar 

  11. M.S. Masoud, A.A. Ibrahim, A.E. Khalil, A. El-Marghany, Spectrochim. Acta Mol. Biomol. Spectrosc. 67, 662 (2007)

    Article  Google Scholar 

  12. O.A. Fathalla, S.M. Awad, M.S. Mohamed, Arch. Pharm. Res. 28, 1205 (2005)

    Article  CAS  Google Scholar 

  13. E.A. El-Helw, H.A. Derbala, M.M. El-Shahawy, M.S. Salem, M.M. Ali, Russ. J. Bioorg. Chem. 45(1), 42 (2019)

    Article  Google Scholar 

  14. A. Odani, H. Kozlowski, J. Swiatek-Kozlowska, J. Brasun, B.P. Operschall, H.J. Sigel, J. Inorg. Biochem. 101, 727 (2007)

    Article  CAS  Google Scholar 

  15. S.K. Ramadan, W.S.I. Abou-Elmagd, Synth. Commun. 48(18), 2409 (2018)

    Article  CAS  Google Scholar 

  16. S.K. Ramadan, S.S. Shaban, A.I. Hashem, Synth. Commun. 50(2), 185 (2020)

    Article  CAS  Google Scholar 

  17. W.S.I. Abou-Elmagd, A.K. El-Ziaty, M.I. Elzahar, S.K. Ramadan, A.I. Hashem, Synth. Commun. 46(14), 1197 (2016)

    Article  CAS  Google Scholar 

  18. S.K. Ramadan, H.A. Sallam, J. Heterocycl. Chem. 55, 1942 (2018)

    Article  CAS  Google Scholar 

  19. S.K. Ramadan, E.A.E. El-Helw, H.A. Sallam, Heterocycl. Commun. 25(1), 107 (2019)

    Article  CAS  Google Scholar 

  20. C.O. Kappe, Eur. J. Med. Chem. 35, 1043 (2000)

    Article  CAS  Google Scholar 

  21. A. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Lett. 44, 857 (2003)

    Article  CAS  Google Scholar 

  22. S.A. Rizk, S.S. Abdelwahab, H.A. Sallam, J. Heterocycl. Chem. 55, 1604 (2018)

    Article  CAS  Google Scholar 

  23. S.A. Rizk, S.S. Abdelwahab, A.A. El-Badawy, J. Heterocycl. Chem. 56, 2347 (2019)

    Article  CAS  Google Scholar 

  24. M.A. Hussein, O.H. Zyaan, A.H. Abdel Monsef, S.A. Rizk, S.M. Farag, S.E. Hafez, A.S. Khaled, O.M. Helmy, Int. J. Mosq. Res. 5, 22 (2018)

    Google Scholar 

  25. S.A. Rizk, A.M. El-Naggar, A.A.J. El-Badawy, Mol. Str. 1155, 720 (2018)

    Article  CAS  Google Scholar 

  26. A.I. Hashem, W.S.I. Abou-Elmagd, A.K. El-Ziaty, S.K. Ramadan, J. Heterocycl. Chem. 54, 3711 (2017)

    Article  CAS  Google Scholar 

  27. S.K. Ramadan, E.A.E. El-Helw, M.E. Azab, Russ. J. Org. Chem. 55(12), 1940 (2019)

    Article  CAS  Google Scholar 

  28. A.K. El-Ziaty, W.S.I. Abou-Elmagd, S.K. Ramadan, A.I. Hashem, Synth. Commun. 47(5), 471 (2017)

    Article  CAS  Google Scholar 

  29. S.K. Ramadan, E.A.E. El-Helw, J. Chem. Res. 42, 332 (2018)

    Article  CAS  Google Scholar 

  30. K.N.M. Halim, S.K. Ramadan, S.A. Rizk, M.A. El-Hashash, Synthesis, DFT study, molecular docking and insecticidal evaluation of some pyrazole-based tetrahydropyrimidine derivatives. Synth. Commun. (2020). https://doi.org/10.1080/00397911.2020.1720739

    Article  Google Scholar 

  31. B.Y. Bhong, P.B. Thorat, N.N. Karade, Tetrahedron Lett. 54(14), 1862 (2013)

    Article  CAS  Google Scholar 

  32. T.J. Mosmann, Immunol. Methods 65, 55 (1983)

    Article  CAS  Google Scholar 

  33. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, M.R. Boyd, J. Natl. Cancer Inst. 82(13), 1107 (1990)

    Article  CAS  Google Scholar 

  34. H.J. Mauceri, N.N. Hanna, M.A. Beckett, D.H. Gorski, M.J. Staba, K.A. Stellato, K. Bigelow, R. Heimann, S. Gately, M. Dhanabal, G.A. Soff, V.P. Sukhatme, D. Kufe, R.R. Weichselbaum, Nature 394, 287 (1998)

    Article  CAS  Google Scholar 

  35. ShM Abu-Bakr, KhM Abouzid, M. Youns, A. Hashim, H.I. El-Diwan, Res. J. Pharm. Biol. Chem. Sci. 4(4), 1350 (2013)

    CAS  Google Scholar 

  36. X. Liu, Y. Guo, Y. Li, Y. Jiang, S. Chubb, A. Azuma, P. Huang, A. Matsuda, W. Hittelman, W. Plunkett, Cancer Res. 65, 6874 (2005)

    Article  CAS  Google Scholar 

  37. X.L. Yu, Y.X. Liu, Y.Q. Li, Q.M. Wang, J. Agric. Food Chem. 63, 9690 (2015)

    Article  CAS  Google Scholar 

  38. R.B. Xu, R. Xia, M. Luo, X.Y. Xu, J.G. Cheng, X.S. Shao, Z. Li, J. Agric. Food Chem. 62, 381 (2014)

    Article  CAS  Google Scholar 

  39. S.A. Abdel-Latef, A.S. Darwish, S.A. Rizk, S.K. Atya, M.E. Helal, J. Mol. Liq. 288, 111006 (2019)

    Article  CAS  Google Scholar 

  40. S.K. Attia, A.T. Elgendy, S.A.J. Rizk, Mol. Str. 1184, 583 (2019)

    Article  CAS  Google Scholar 

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Acknowledgements

Technical support from Chemistry Department, Faculty of Science, Ain Shams University is gratefully acknowledged.

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The authors received no specific funding for this work.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Ain Shams University, Abassia, Cairo, 11566, Egypt

    Sayed K. Ramadan, Karema N. M. Halim, Sameh A. Rizk & Maher A. El-Hashash

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  1. Sayed K. Ramadan
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  2. Karema N. M. Halim
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  3. Sameh A. Rizk
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Correspondence to Sayed K. Ramadan.

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Ramadan, S.K., Halim, K.N.M., Rizk, S.A. et al. Cytotoxic activity and density functional theory studies of some 1,3-diphenylpyrazolyltetrahydropyrimidine derivatives. J IRAN CHEM SOC 17, 1575–1589 (2020). https://doi.org/10.1007/s13738-020-01880-8

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  • DOI: https://doi.org/10.1007/s13738-020-01880-8

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