Skip to main content
SpringerLink
Log in

Synthesis and Anticancer Activity of New Pyrimidine and Oxadiazole Acyclic Nucleoside Analogs and Thiazolopyrimidine Derivatives

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

Abstract

A group of new substituted pyrimidine compounds, and their thiazolopyrimidines and 1,3,4-oxadiazolyl acyclic sugar derivatives have been synthesized as potential anti-cancer candidates. Oxadiazolyl-pyrimidine hybrid compounds have been synthesized by the reaction of thioacetohydrazide derivative with carbon disulfide and heterocyclization of sugar hydrazones with acetic anhydride. The synthesized products have been studied for their anticancer activity against human liver carcinoma (HepG-2) and human normal retina pigmented epithelium (RPE-1). The synthesized sugar hydrazine of D-glucose, its 1,3,4-oxadiazole acyclic nucleoside and arylidine derivative demonstrate high selective anti-cancer activity against liver cell line without side effects on normal cells.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Scheme 2.
Fig. 1.
Scheme 3.

Similar content being viewed by others

REFERENCES

  1. Kaur, N., Kaur, K., Raj, T., Kaur, G., Singh, A., Aree, T., Park, S.J., Kim, T.J., Singh, N., and Jang, D.O., Tetrahedron, 2015, vol. 71, p. 332. https://doi.org/10.1016/j.tet.2014.11.039

    Article  CAS  Google Scholar 

  2. Bhalgat, C.M., Ali, M.I., Ramesh, B., and Ramu, G., Arabian J. Chem., 2014, vol. 7, p. 986. https://doi.org/10.1016/j.arabjc.2010.12.021

    Article  CAS  Google Scholar 

  3. Lal, K., Paliwal, L.J., and Bagade, M.B., Lett. Org. Chem., 2016, vol. 13, p. 255. https://doi.org/10.2174/1570178613666160224005811

    Article  CAS  Google Scholar 

  4. Klein, E., DeBonis, S., Thiede, B., Skoufias, D.A., Kozielskib, F., and Lebeau, L., Bio. Org. Med. Chem., 2007, vol. 15, p. 6474. https://doi.org/10.1016/j.bmc.20070.6.016

    Article  CAS  Google Scholar 

  5. Hassan, M.F. and Khalid, A.K., J. Fluor.Chem., 2012, vol. 142, p. 96. https://doi.org/10.1016/j.jfluchem.2012.06.032

    Article  CAS  Google Scholar 

  6. Lal, K., Paliwal, L.J., and Bagade, M.B., Materials, 2018, vol. 5, p. 15354. https://doi.org/10.1016/j.matpr.2018.05.017

    Article  CAS  Google Scholar 

  7. Quiroga, J., Romo, P.E., Ortiz, A., Isaza, J.H., Insuasty, B., Abonia, R., Nogueras, M., and Cobo, J., J. Mol. Struc., 2016, vol. 1120, p. 294. https://doi.org/10.1016/j.molstruc.2016.05.045

    Article  CAS  Google Scholar 

  8. Parveen, H., Hayat, F., Salahuddin, A., and Azam, A., Eur. J. Med. Chem., 2010, vol. 45, p. 3497. https://doi.org/10.1016/j.ejmech.2010.04.023

    Article  CAS  PubMed  Google Scholar 

  9. El-Nassan, H. B., Eur. J. Med. Chem., 2011, vol. 46, p. 2031. https://doi.org/10.1016/j.ejmech.2011.02.055

    Article  CAS  PubMed  Google Scholar 

  10. Yousif, M.N.M., El-Sayed, W.A., Abbas, H.S., Awad, H.M., and Yousif, N.M., J. App. Pharm. Sci., 2017, vol. 7, p. 21. https://doi.org/10.7324/JAPS.2017.71104

    Article  CAS  Google Scholar 

  11. Tolan, H.E.M., El-Sayed, W.A., Tawfek, N., Abdel-Megeid, F.M.E., and Kutkat, O.M., Nucleos. Nucleot. Nucleic Acids, 2020, vol. 39, p. 649. https://doi.org/10.1080/15257770.2019.1674331

    Article  CAS  Google Scholar 

  12. Nassar, I.F., El Farargy, A.F., Abdelrazek, F.M., and Ismail, N.S.M., Nucleos. Nucleot. Nucleic Acids, 2017, vol. 36, p. 275. https://doi.org/10.1080/15257770.2016.1276290

    Article  CAS  Google Scholar 

  13. Khalaf, H.S., Tolan, H.E.M., Radwan, M.A.A., Mohamed, A.M., Awad, H.M., and El-Sayed, W.A., Nucleos. Nucleot. Nucleic Acids, 2020, vol. 39, p. 1036. https://doi.org/10.1080/15257770.2020.1748649

    Article  CAS  Google Scholar 

  14. Nassar, I.F., Att-Allah S.R., and Hemdan, M.M., Phosphorous, Sulphur and Silicon., 2018, vol. 193, p. 630. https://doi.org/10.1080/10426507.2018.1487435

  15. Nassar, I.F., El-Sayed, W.A., Ragab, T.I.M., Shalaby, A.-S.G., and Mehany, A.B.M., Mini Rev. Med. Chem., 2019, vol. 19, p. 395. https://doi.org/10.2174/1389557518666180820125210

    Article  CAS  PubMed  Google Scholar 

  16. Warmus, J.S., Flamme, C., Zhang, L.Y., Barrett, S., Bridges, A., Chen, H., Gowan, R., Kaufman, M., SeboltLeopold, J., Leopold, W., Merriman, R., Ohren, J., Pavlovsky, A., Przybranowski, S., Tecle, H., Valik, H., Whitehead, C., and Zhang, E., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 6171. https://doi.org/10.1016/j.bmcl.2008.10.015

    Article  CAS  PubMed  Google Scholar 

  17. Sankhe, N.M., Durgashivaprasad, E., Gopalan Kutty, N., Venkata Rao, J., Narayanan, K., Kumar, N., Jain, P., Udupa, N., and Vasanth Raj, P., Arabian J. Chem., 2019, vol. 12, p. 2548. https://doi.org/10.1016/j.arabjc.2015.04.030

    Article  CAS  Google Scholar 

  18. Khanam, R., Ahmad, K., Hejazi II, I.A., Siddique, V., Kumar, A.R., Bhat, A., and Azam, F.A., Cancer Chemother. Pharmacol., 2017, vol. 80, p. 1027. https://doi.org/10.1007/s00280-017-3414-6

    Article  CAS  PubMed  Google Scholar 

  19. Mohan, C.D., Anilkumar, N.C., Rangappa, S., Shanmugam, M.K., Mishra, S., Chinnathambi, A., Alharbi, S.A., Bhattacharjee, A., Sethi, G., Kumar, A.P., and Basappa Rangappa, K.S., Front. Oncol., 2018, vol. 8, p. 42. https://doi.org/10.3389/fonc.2018.00042

  20. El-Sayed, W.A., Osman, D.A.A., Khalaf, H.S., Abbas, H.S., and Ali, M.M., Acta. Pol. Pharm. Drug. Res., 2017, vol. 74, p. 1739.

  21. Kerru, N., Singh, P., Koorbanally, N., Raj, R., and Kumar, V., Eur. J. Med. Chem., 2017, vol. 142, p. 179. https://doi.org/10.1016/j.ejmech.2017.07.033

    Article  CAS  PubMed  Google Scholar 

  22. El-Sayed, W.A., Nassar, I.F., and Abdel-Rahman, A.A., J. Heterocycl. Chem., 2010, vol. 48, p. 135. https://doi.org/10.1002/jhet.522

    Article  CAS  Google Scholar 

  23. Kassem, A.F., Nassar, I.F., Abdel-Aal, M.T., Awad, H.M., and El-Sayed, W.A., Chem. & Pharm. Bull., 2019, vol. 67, p. 888. https://doi.org/10.1248/cpb.c19-00280

    Article  CAS  Google Scholar 

  24. Basiony, E.A., Hassan, A.A., Al-Amshany, Z.M., Abd-Rabou, A.A., Abdel-Rahman, A.A., Hassan, N.A., and El-Sayed, W.A., Molecules, 2020, vol. 25, p. 399. https://doi.org/10.3390/molecules25020399

  25. Nassar, I.F., J. Heterocycl. Chem., 2013, vol. 50, p. 129. https://doi.org/10.1002/jhet.1022

    Article  CAS  Google Scholar 

  26. El-Sayed, W.A., El-Sofany, W.I., Hussein, H.A.R., and Fathy, N.M., Nucleos. Nucleot. Nucleic Acids., 2017, vol. 36. p. 474. https://doi.org/10.1080/15257770.2017.1327665

    Article  CAS  Google Scholar 

  27. Hamdy, N.A., Anwar, M.M., Abu-Zied, K.M., and Awad, H.M., Acta. Pol. Pharm. Drug. Researc., 2013, vol. 70, p. 987. PMID: 24383322

    CAS  Google Scholar 

  28. Abdel Rahman, A.A., Nassar, I.F., Shaban, A.K.F., El-Kady, D.S., Awad, H.M., and El Sayed, W.A., Mini Rev. Med. Chem., 2019, vol. 19, p. 1093. https://doi.org/10.2174/1389557519666190312165717

    Article  CAS  Google Scholar 

  29. Almajhdi, F.N., Fouad, H., Khalil, K.A., Awad, H.M., Mohamed, S.H.S., Elsarnagawy, T., Albarrag, A.M., Al-Jassir, F.F., and Abdo, H.S., J. Mater. Sci. Mater. Med., 2014, vol. 25, p. 1045. https://doi.org/10.1007/s10856-013-5131-y

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Menofia University, 32511, Shebin El-Kom, Egypt

    A. A. H. Abdel Rahman & A. K. F. Shaban

  2. Faculty of Specific Education, Ain Shams University, Abassia, 11772, Cairo, Egypt

    I. F. Nassar

  3. Photochemistry Department, National Research Centre, 12622, Cairo, Egypt

    M. N. M. Yousif & W. A. El-Sayed

  4. Hormone Department, National Research Centre, Dokki, 12622, Cairo, Egypt

    D. S. El-Kady

  5. Tanning Materials and Leather Technology Department, National Research Centre, Dokki, 12622, Cairo, Egypt

    H. M. Awad

  6. Department of Chemistry, College of Science, Qassim University, 51452, Buraydah, Saudi Arabia

    W. A. El-Sayed

Authors
  1. A. A. H. Abdel Rahman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. K. F. Shaban
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. F. Nassar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. N. M. Yousif
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. S. El-Kady
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. H. M. Awad
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. W. A. El-Sayed
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to W. A. El-Sayed.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rahman, A.A.H.A., Shaban, A.K.F., Nassar, I.F. et al. Synthesis and Anticancer Activity of New Pyrimidine and Oxadiazole Acyclic Nucleoside Analogs and Thiazolopyrimidine Derivatives. Russ J Gen Chem 91, 2086–2094 (2021). https://doi.org/10.1134/S1070363221100261

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221100261

Keywords:

Search

Navigation