Skip to main content
SpringerLink
Log in

First Analog of Pyrimidine Nucleosides with Two D-Ribofuranose Residues

  • Short Communications
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The reaction of 1,3-bis(pent-4-yn-1-yl)-6-methyluracil with 2,3,5-tri-O-acetyl-β-D-ribofuranosyl azide gave 1,3-bis{3-[1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,3-triazol-4-yl]propyl}-6-methyluracil which was deprotected by treatment with a solution of sodium methoxide in methanol to obtain 1,3-bis{3-[1-(β-D-ribofuranosyl)-1H-1,2,3-triazol-4-yl]propyl]-6-methyluracil as a first analog of pyrimidine nucleosides containing two D-ribofuranose fragments.

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

References

  1. Matyugina, E.S., Khandazhinskaya, A.L., and Kochetkov, S.N., Russ. Chem. Rev., 2012, vol. 81, p. 729. https://doi.org/10.1070/RC2012v081n08ABEH004314

    Article  CAS  Google Scholar 

  2. Hernandez, D. and Boto, A., Eur. J. Org. Chem., 2014, no. 11, p. 2201. https://doi.org/10.1002/ejoc.201301731

  3. Jahnz-Wechmann, Z., Framski, G., Januszczyk, P., and Boryski, J., Eur. J. Med. Chem., 2015, vol. 97, p. 388. https://doi.org/10.1016/j.ejmech.2014.12.026

    Article  CAS  Google Scholar 

  4. Gish, R.G., J. Antimicrob. Chemother., 2006, vol. 57, p. 8. https://doi.org/10.1093/jac/dki405

    Article  CAS  Google Scholar 

  5. Shmalenyuk, E.R., Chernousova, L.N., Karpenko, I.L., Kochetkov, S.N., Smirnova, T.G., Andreevskaya, S.N., Chizhov, A.O., Efremenkova, O.V., and Alexandrova, L.A., Bioorg. Med. Chem., 2013, vol. 21, p. 4874. https://doi.org/10.1016/j.bmc.2013.07.003

    Article  CAS  Google Scholar 

  6. Ruddarraju, R.R., Murugulla, A.C., Kotla, R., Tirumalasetty, M.C.B., Wudayagiri, R., Donthabakthuni, S., Maroju, R., Baburao, K., and Parasa, L.S., Eur. J. Med. Chem., 2016, vol. 123, p. 379. https://doi.org/10.1016/j.ejmech.2016.07.024

    Article  CAS  Google Scholar 

  7. Semenov, V.E., Nikolaev, A.E., Krylova, E.S., Sharafutdinova, D.R., and Reznik, V.S., Russ. J. Org. Chem., 2012, vol. 48, p. 582. https://doi.org/10.1134/S1070428012040203

    Article  CAS  Google Scholar 

  8. Voloshina, A.D., Semenov, V.E., Strobykina, A.S., Kulik, N.V., Krylova, E.S., Zobov, V.V., and Reznik, V.S., Russ. J. Bioorg. Chem., 2017, vol. 43, p. 170. https://doi.org/10.1134/S1068162017020170

    Article  CAS  Google Scholar 

  9. Gabdrakhmanov, D.R., Samarkina, D.A., Krylova, E.S., Kapitanov, I.V., Karpichev, Y., Latypov, S.K., Semenov, V.E., Nizamev, I.R., Kadirov, M.K., and Zakharova, L.Y., J. Surfactants Deterg., 2019, vol. 22, p. 865. https://doi.org/10.1002/jsde.12257

    Article  CAS  Google Scholar 

  10. Nisik, F., Speciale, G., and Bernatdi, A., Chem. Eur. J., 2012, vol. 18, p. 6895. https://doi.org/10.1002/chem.201200309

    Article  Google Scholar 

Download references

Acknowledgments

The authors thank the Spectral and Analytical Joint Center (Kazan Scientific Center, Russian Academy of Sciences) for technical support of the present study.

Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-13-00003).

Author information

Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, 420088, Russia

    R. R. Sharipova, L. F. Saifina, M. G. Belenok, V. E. Semenov & V. E. Kataev

Authors
  1. R. R. Sharipova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. F. Saifina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. G. Belenok
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. E. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. E. Kataev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. E. Kataev.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 148–152.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sharipova, R.R., Saifina, L.F., Belenok, M.G. et al. First Analog of Pyrimidine Nucleosides with Two D-Ribofuranose Residues. Russ J Org Chem 56, 181–184 (2020). https://doi.org/10.1134/S1070428020010285

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020010285

Keywords

Search

Navigation