Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 8, pp 1673–1682 | Cite as

Synthesis and Anticancer Activity of New Substituted Piperidinones Linked to Pyrimidine, Thiazole, and Triazole Glycoside Derivatives

  • M. N. M. YousifEmail author
  • I. F. Nassar
  • N. M. Yousif
  • H. M. Awad
  • W. A. El-SayedEmail author
Article
  • 13 Downloads

Abstract

New piperidinone incorporating pyrimidine, triazine, diazipine, oxatriazine, and thiazole derivatives have been synthesized starting with tetramethylpipridin-4-one. Structures of the newly synthesized compounds are characterized on the basis of spectroscopic and analytical data. The anticancer activity of the prepared compounds has been studied in vitro against HCT-116 and MCF-7 human cancer cells using the MTT assay. A number of compounds demonstrates potent activity towards both cell lines with IC50 values comparable with doxorubicin.

Keywords

piperidinone pyrimidine thiazolopyrimidine diazipine oxatriazine thiazole anticancer HCT-116 MCF-7 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

References

  1. 1.
    Janssens, F.J., Torremans, and Janssen, P.A., J. Med. Chem., 1986, vol. 29, p. 2290. doi  https://doi.org/10.1021/jm00161a027 CrossRefGoogle Scholar
  2. 2.
    Sato, I., Morihira, K., Inami, H., Kubota, H., Morokata, T., Suzuki, K., Hamada, N., Iura, Y., Nitta, A., Imaoka, T., Takahashi, T., Takeuchi, M., Ohta, M., and Tsukamotoa, S., Bioorg. & Med. Chem., 2008, vol. 16, p. 144. doi  https://doi.org/10.1016/j.bmc.2007.10.003 CrossRefGoogle Scholar
  3. 3.
    Smirk, F.H. and Hodge, J.V., J. Chin. Pharm. Therap., 1960, vol. 1, p. 610.Google Scholar
  4. 4.
    Spinks, A. and Young, E.H.P., Nature, 1958, vol. 181, p. 1397.CrossRefGoogle Scholar
  5. 5.
    Corne, S.J. and Edge, N. D., Brit. J. Pharmacol., 1958, vol. 13, p. 339.Google Scholar
  6. 6.
    Guziec, Jr.F.S. and Torres, F.F., J. Org. Chem., 1993, vol. 58, p. 1604. doi:  https://doi.org/10.1021/jo00058a055 CrossRefGoogle Scholar
  7. 7.
    Nassar, I.F., El-Sayed, W.A., Ragab, T.I.M., Shalaby, A.G., and Mehany, A.B.M., Mini Rev. Med. Chem., 2019, vol. 19(5), p. 395. doi  https://doi.org/10.2174/1389557518666180820125210 CrossRefGoogle Scholar
  8. 8.
    El-Sayed, W.A., Mohamed, A.M., Khalaf, H.S., El-Kady, D.S., and Al-Manawaty, M., J. Appl. Pharm. Sci., 2017, vol. 7(9), p. 1. doi  https://doi.org/10.7324/JAPS.2017.70901 Google Scholar
  9. 9.
    El-Sayed, W.A., El-Sofany, W.I., Hussein, H.A., and Fathi, N.M., Nucleosides, Nucleotides and Nucleic Acids, 2017, vol. 36, p. 474. doi  https://doi.org/10.1080/15257770.2017.1327665 CrossRefGoogle Scholar
  10. 10.
    El-Sayed, W.A., Khalaf, H.S., Osman, D.A.A., Abbas, H.S., and Ali, M.M., Acta Polonea Pharm.-Drug Res., 2017, vol. 74(6), 1739.Google Scholar
  11. 11.
    Abbas, H.S., El Sayed, W.A., and Fathy, N.M., Eur. J. Med. Chem., 2010, vol. 45, p. 973. doi  https://doi.org/10.1016/j.ejmech.2009.11.039 CrossRefGoogle Scholar
  12. 12.
    Corey, E.J. and Gross, W.A., J. Org. Chem., 1985, vol. 50, p. 5391. doi  https://doi.org/10.1021/jo00225a082 CrossRefGoogle Scholar
  13. 13.
    Keana, T.F.W., Chem. Rev., 1978, vol. 78, p. 37. doi  https://doi.org/10.1021/cr60311a004 CrossRefGoogle Scholar
  14. 14.
    Hook, R., Ind. Eng. Chem. Res., 1997, vol. 36, p. 1779. doi  https://doi.org/10.1021/ie9605589 CrossRefGoogle Scholar
  15. 15.
    Chakraboty, A.K., Astarita, G., and Bischoff, K.B., Chem. Eng. Sci., 1985, vol. 41, p. 997. doi  https://doi.org/10.1016/0009-2509(86)87185-8 CrossRefGoogle Scholar
  16. 16.
    Sapanara, S., Ferrara, A., Gorelli, B., Shah, A., Kawase, M., Motohashi, N., Molnar, J., Sgaragli, G., and Fusia, F., Eur. J. Pharm., 2007, vol. 563, p. 160. doi  https://doi.org/10.1016/j.ejphar.2007.02.001 CrossRefGoogle Scholar
  17. 17.
    Kawase, M., Shah, A., Gaveriya, H., Motohashi, N., Sakagami, H., Varga, A., and Molnar, J., Bioorg. Med. Chem., 2002, vol. 10, p. 1051. doi  https://doi.org/10.1016/S0968-0896(01)00363-7 CrossRefGoogle Scholar
  18. 18.
    Tasaka, S., Ohmori, H., Gomi, N., Lino, M., Machida, T., Kuie, A., Naito, S., and Kuwano, M., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 275. doi  https://doi.org/10.1016/S0960-894X(00)00651-X. CrossRefGoogle Scholar
  19. 19.
    Gunars, T., Dace, T., and Zhanna, H., Czech. J. Food Sci., 2001, vol. 19(3), p. 81. doi  https://doi.org/10.17221/6581-CJFS Google Scholar
  20. 20.
    Tirzite, D., Krauze, A., Zubareva, A., Tiritis, G., and Duburs, G., Chem. Heterocycl. Comp., 2002, vol. 38(7), p. 795.CrossRefGoogle Scholar
  21. 21.
    Kumar, A., Mavrya, R. A., Sharma, S., Kumar, M., and Bhatia, G., Eur. J. Med. Chem., 2010, vol. 45, p. 501. doi  https://doi.org/10.1016/j.ejmech.2009.10.036 CrossRefGoogle Scholar
  22. 22.
    El-Hashash, M.A. and El-Kady, M., Rev. Roum. Chim., 1978, vol. 23, p. 581.Google Scholar
  23. 23.
    Skehan, P., Storenge, R., Scudiero, D., Monks, A., Mcmahon, J., Vistica, D., Warren, J.T., Bokesch, H., Kenney, S., and Boyd, M.R., J. Nat. Cancer Inst., 1990, vol. 82, p. 1107. doi  https://doi.org/10.1093/jnci/82.13.1107 CrossRefGoogle Scholar
  24. 24.
    Li, E., Beard, C., and Jaenisch, R., Nature, 1993, vol. 366, p. 362.CrossRefGoogle Scholar
  25. 25.
    Soliman, H.A., Yousif, M.N.M., Said, M.M., Hassan, N.A., Ali, M.M., Awad H.M., and Abdel-Megeid F.M.E., Der Pharma Chemica, 2014, vol. 6(3), p. 394.Google Scholar
  26. 26.
    Yousif, M.N.M., Ph.D. Thesis, Faculty of pharmacy, Cairo University, 2015.Google Scholar
  27. 27.
    Dickerman, S.C. and Lindwall, H.G., J. Org. Chem., 1949, vol. 14(4), p. 530. doi  https://doi.org/10.1021/jo01156a005 CrossRefGoogle Scholar
  28. 28.
    Yousif, M.N.M., Hussein, H.A.R., Yousif, N.M., El-Manawaty, M.A., and El-Sayed W.A., J. Appl. Pharm. Sci., 2019, vol. 9(01), p. 6. doi  https://doi.org/10.7324/JAPS.2019.90102 CrossRefGoogle Scholar
  29. 29.
    Yousif, M.N.M., El-Sayed, W.A., Abbas, S., Awad, H.M., Yousif, N.M., J. Appl. Pharm. Sci., 2017, vol. 7(11), p. 21. doi  https://doi.org/10.7324/JAPS.2017.71104 Google Scholar
  30. 30.
    El-Sayed, W.A., Khalaf, H.S., Mohamed, S.F., Hussien, H.A., Kutkat, O.M., and Amr, A.E., Russ. J. Gen. Chem., 2017, vol. 87(10), p. 2444. doi  https://doi.org/10.1134/S1070363217100279 CrossRefGoogle Scholar
  31. 31.
    Hassan, A.S, Mady, M.F, Awad, H.M, and Hafez, T.S., Chin. Chem. Lett., 2017, vol. 28(2), p. 388. doi  https://doi.org/10.1016/j.cclet.2016.10.022. CrossRefGoogle Scholar
  32. 32.
    Mohamed, S.F., Kotb, E.R., Abd El-Meguid, E.A., and Awad, H.M., Res. on Chem. Interm., 2017, vol. 43(1), p. 437. doi  https://doi.org/10.1007/s11164-016-2633-5 CrossRefGoogle Scholar
  33. 33.
    Flefel, E.M., El-Sayed, W.A., Mohamed, A.M., El-Sofany, W.I., and Awad, H.M., Molecules, 2017, vol. 22(170), p. 1. doi  https://doi.org/10.3390/molecules22010170 Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  1. 1.Photochemistry DepartmentNational Research CentreCairoEgypt
  2. 2.Faculty of Specific EducationAin Shams UniversityCairoEgypt
  3. 3.Tanning Materials and Leather Technology DepartmentNational Research CentreDokki, CairoEgypt
  4. 4.Chemistry Department, Faculty of ScienceQassim UniversityBuraydahSaudi Arabia

Personalised recommendations