Skip to main content
SpringerLink
Log in

Synthesis of 2-triazolylpurine Phosphonates

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A series of novel compounds containing triazole and phosphonate moieties were obtained under mild conditions. Reactions of 2,6-bis-(triazolyl)purine acyclic nucleoside phosphonates, in which triazole ring at C-6 atom of purine was acting as a good leaving group, and N- or S-nucleophiles allowed to obtain the respective 2-triazolylpurine phosphonates in 62–87% yields.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Figure 1.
Figure 2.

Similar content being viewed by others

Explore related subjects

Discover the latest articles, news and stories from top researchers in related subjects.

References

  1. (a) De Clercq, E.; Holý, A. Nat. Rev. Drug Discovery 2005, 4, 928. (b) Holý, A. Antiviral Res. 2006, 71, 248. (c) De Clercq, E. Biochem. Pharmacol. 2011, 82, 99.

  2. (a) Andrei, G.; Topalis, D.; De Schutter, T.; Snoeck, R. Antiviral Res. 2015, 114, 21. (b) Lin, C.-L.; Yang, H.-C.; Kao, J.-H. Liver Int. 2016, 36, 85.

  3. Macchi, B.; Romeo, G.; Chiacchio, U.; Frezza, C.; Giofrè, S. V.; Marino-Merlo, F.; Mastino, A. Phosphonated Nucleoside Analogues as Antiviral Agents; Springer: Berlin, 2013, Vol. 10, p. 53.

    Google Scholar 

  4. (a) Klejch, T.; Pohl, R.; Janeba, Z.; Sun, M.; Keough, D. T.; Guddat, L. W.; Hocková, D. Tetrahedron 2018, 74, 5886. (b) Klejch, T.; Keough, D. T.; Chavchich, M.; Travis, J.; Skácel, J.; Pohl, R.; Janeba, Z.; Edstein, M. D.; Avery, V. M.; Guddat, L. W.; Hocková, D. Eur. J. Med. Chem. 2019, 183, 111667. (c) Keough, D. T.; Hockova, D.; Janeba, Z.; Wang, T.-H.; Naesens, L.; Edstein, M. D. J. Med. Chem. 2015, 58, 827. (d) Cheviet, T.; Wein, S.; Bourchenin, G.; Lagacherie, M.; Périgaud, C.; Cerdan, R.; Peyrottes, S. J. Med. Chem. 2020, 63, 8069. d Keough, D. T.; Hocková, D.; Holý, A.; Naesens, L. M. J.; Skinner-Adams, T. S.; de Jersey, J.; Guddat, L. W. J. Med. Chem. 2009, 52, 4391. e de Jersey, J.; Holý, A.; Hockova, D.; Naesens, L.; Keough, D. T.; Guddat, L. W. Curr. Top. Med. Chem. 2011, 11, 2085.

  5. Břehová, P.; Šmídková, M.; Skácel, J.; Dračínský, M.; Mertlíková-Kaiserová, H.; Velasquez, M. P. S.; Watts, V. J.; Janeba, Z. ChemMedChem 2016, 11, 2534.

    Article  Google Scholar 

  6. (a) Pomeisl, K.; Beier, P.; Pohl, R.; Krečmerová, M. ChemistrySelect 2016, 1, 2102. (b) Pomeisl, K.; Krečmerová, M.; Pohl, R.; Snoeck, R.; Andrei, G. Tetrahedron 2019, 75, 130529. (c) Kim, C. U.; Luh, B. Y.; Misco, P. F.; Bronson, J. J.; Hitchcock, M. J. M.; Ghazzouli, I.; Martin, J. C. J. Med. Chem. 1990, 33, 1207.

  7. Brel, V. K. Synthesis 2012, 2359.

  8. (a) Hocková, D.; Janeba, Z.; Naesens, L.; Edstein, M. D.; Chavchich, M.; Keough, D. T.; Guddat, L. W. Bioorg. Med. Chem. 2015, 23, 5502. (b) Hocková, D.; Rosenbergová, Š.; Ménová, P.; Páv, O.; Pohl, R.; Novák, P.; Rosenberg, I. Org. Biomol. Chem. 2015, 13(15), 4449. (c) Głowacka, I. E.; Piotrowska, D. G.; Andrei, G.; Schols, D.; Snoeck, R.; Wróblewski, A. E. Monatsh. Chem. 2016, 147, 2163.

  9. Sahu, P. K.; Kim, G.; Nayak, A.; Ahn, J. Y.; Ha, M. W.; Park, C.; Yu, J.; Park, H.-G.; Jeong, L. S. Asian J. Org. Chem. 2016, 5, 183.

    Article  CAS  Google Scholar 

  10. Malnuit, V.; Smoleń, S.; Tichý, M.; Poštová Slavětínská, L.; Hocek, M. Eur. J. Org. Chem. 2019, 5409.

  11. (a) Baszczyňski, O.; Jansa, P.; Dračínský, M.; Klepetářová, B.; Holý, A.; Votruba, I.; de Clercq, E.; Balzarini, J.; Janeba, Z. Bioorg. Med. Chem. 2011, 19, 2114. (b) Manvar, A.; Shah, A. Tetrahedron 2013, 69, 680. (c) Fu, X. Z.; Ou, Y.; Xin, J.; Yang, Y. S. Chin. Chem. Lett. 2011, 22, 1387.

  12. (a) Novosjolova, I.; Bizdēna, Ē.; Turks, M. Eur. J. Org. Chem. 2015, 3629. (b) Jovaisaite, J.; Cīrule, D.; Jeminejs, A.; Novosjolova, I.; Turks, M.; Baronas, P.; Komskis, R.; Tumkevicius, S.; Jonusauskas, G.; Jursenas, S. Phys. Chem. Chem. Phys. 2020, 22, 26502.

  13. (a) Kovaļovs, A.; Novosjolova, I.; Bizdēna, Ē.; Bižāne, I.; Skardziute, L.; Kazlauskas, K.; Jursenas, S.; Turks, M. Tetrahedron Lett. 2013, 54, 850. (b) Novosjolova, I.; Bizdēna, Ē.; Turks, M. Tetrahedron Lett. 2013, 54, 6557. (c) Novosjolova, I.; Bizdēna, Ē.; Turks, M. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1236.

  14. (a) Lomoschitz, C. J.; Feichtenschlager, B.; Moszner, N.; Puchberger, M.; Müller, K.; Abele, M.; Kickelbick, G. Langmuir 2011, 27, 3534. (b) Cristau, H. J.; Virieux, D. Tetrahedron Lett. 1999, 40, 703.

  15. Ozols, K.; Cīrule, D.; Novosjolova, I.; Stepanovs, D.; Liepinsh, E.; Bizdēna, Ē.; Turks, M. Tetrahedron Lett. 2016, 57, 1174.

    Article  CAS  Google Scholar 

  16. Houghton, S. R.; Melton, J.; Fortunak, J.; Brown Ripin, D. H.; Boddy, C. N. Tetrahedron 2010, 66, 8137.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 Paula Valdena St, Riga, LV-1048, Latvia

    Zigfrīds Kapilinskis, Irina Novosjolova, Ērika Bizdēna & Māris Turks

Authors
  1. Zigfrīds Kapilinskis
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Irina Novosjolova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ērika Bizdēna
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Māris Turks
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Irina Novosjolova.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 55–62

Supplementary Information

ESM 1

(PDF 3255 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kapilinskis, Z., Novosjolova, I., Bizdēna, Ē. et al. Synthesis of 2-triazolylpurine Phosphonates. Chem Heterocycl Comp 57, 55–62 (2021). https://doi.org/10.1007/s10593-021-02867-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02867-w

Keywords

Search

Navigation