Skip to main content

Advertisement

SpringerLink
Log in

Facile synthesis of 6-(heptadec-8-enyl)thiopyrimidines incorporating glycosyl moiety and their antitumor activity

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A facile, convenient, and high yielding synthesis of a new series of pyrimidine N- and S-glycosides incorporating an oleyl residue from readily available starting materials was developed. The key step of this protocol is the formation of a 2-thioxopyrimidine as aglycon which is coupled with an activated cyclic and acyclic halo sugar in the presence of sodium hydride. In addition, 5-fluorouracil analogues containing an oleyl moiety were prepared. The in vitro anticancer activity of the newly synthesized compounds was evaluated against two human cancer cell lines, namely MCF-7 (breast) and HEPG2 (liver) carcinoma. The compounds exhibited moderate to high activities with IC 50 values of 13.2–34.2 μM for MCF-7 and 16.2–63.8 μM for HEPG-2 cell lines. 5-Fluorouracil derivatives incorporating a fatty residue are therefore potent against both cell lines.

Graphical abstract

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

Similar content being viewed by others

References

  1. Matsuda A, Sasaki T (2004) Cancer Sci 95:105

    Article  CAS  Google Scholar 

  2. Heidelberelberger C, Leibbman KC, Bhargava PM (1957) Cancer Res 17:39

    Google Scholar 

  3. Malet-Martino M, Jolimaitre P, Martino R (2002) Curr Med Chem Anticancer Agents 2:267

    Article  CAS  Google Scholar 

  4. Straus MJ, Mante N, Golden A (1960) Cancer Res 33:201

    Google Scholar 

  5. Li J, Xu L, He KL, Juo WJ, Zheng YH, Xia P, Chen Y (2001) Breast Cancer Res 3:253

    Article  CAS  Google Scholar 

  6. Rauf A, Parveen H (2005) Indian J Chem 44B:1273

    CAS  Google Scholar 

  7. Rauf A, Banday MR, Mattoo RM (2008) Acta Chim Slov 55:448

    CAS  Google Scholar 

  8. Ahmed SM, Ahmed F, Osman SM (1985) J Am Oil Chem Soc 62:1578

    Article  CAS  Google Scholar 

  9. Khan MWY, Ahmed F, Ahmed I, Osman SM (1983) J Am Oil Chem Soc 60:949

    Article  CAS  Google Scholar 

  10. Mujeebur-Rahman VP, Mukhtar S, Ansari WH, Lemiere G (2005) Eur J Med Chem 40:173

    Article  Google Scholar 

  11. Banday MR, Rauf A (2009) Indian J Chem 48B:97

    CAS  Google Scholar 

  12. Uhlmann E, Peyman A (1990) Chem Rev 90:543

    Article  CAS  Google Scholar 

  13. Agrawalides S (1999) Biochem Biophys Acta 53:1489

    Google Scholar 

  14. Han MJ, Chang JY (2000) Polynucleotide analogues. Advances in polymer science, vol 153. Springer, Berlin

  15. Miller K, Sudip K (1998) Pharm Sci Technol Today 1:377

    Article  CAS  Google Scholar 

  16. Hammud H, Ghnoum M, Fares A, Abramian K, Bouhadir H (2008) J Mol Struct 881:11

    Article  CAS  Google Scholar 

  17. Abu-Zaied MA, Nawwar GAM, Swellam RH (2012) Pharmacol Pharm 3:254

    Article  CAS  Google Scholar 

  18. Abd El Salam HA, Shaker NO, El Telbani EM, Nawwar GAM (2009) J Chem Res 40:400

    Google Scholar 

  19. Abu-Zaied MA, El-Telbani EM, Elgemeie GH, Nawwar GAM (2010) Eur J Med Chem 46:229

    Article  Google Scholar 

  20. Hafez HN, El-Gazzar AB, Nawwar GAM (2010) Eur J Med Chem 45:1485

    Article  CAS  Google Scholar 

  21. Demchenko AV (2008) Handbook of chemical glycosylation: advances in stereoselectivity and therapeutic relevance. Wiley-VCH, Weinheim

    Book  Google Scholar 

  22. Abdel-Rahman AAH, Pedersen EB, Nielsen C (1996) Monatsh Chem 127:455

    Article  CAS  Google Scholar 

  23. Skehan P, Stroeng R, Scudiero D (1990) J Natl Cancer Inst 82:1107

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Institute of Cancer, Cairo, Egypt.

Author information

Authors and Affiliations

  1. Department of Green Chemistry, National Research Centre (NRC), Tahrir St., Dokki, Giza, Egypt

    Hayam A. Abd El Salam, El-Sayed M. A. Yakout & Galal A. M. Nawwar

  2. Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt

    M. A. El-Hashash

Authors
  1. Hayam A. Abd El Salam
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. El-Sayed M. A. Yakout
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. El-Hashash
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Galal A. M. Nawwar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to El-Sayed M. A. Yakout.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abd El Salam, H.A., Yakout, ES.M.A., El-Hashash, M.A. et al. Facile synthesis of 6-(heptadec-8-enyl)thiopyrimidines incorporating glycosyl moiety and their antitumor activity. Monatsh Chem 144, 1893–1901 (2013). https://doi.org/10.1007/s00706-013-1069-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-013-1069-5

Keywords

Search

Navigation