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3-Halopyrazolo[1,5-a]pyrimidines as promising precursors of novel C-nucleosides

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Abstract

Various approaches to the synthesis of 3-halopyrazolo[1,5-a]pyrimidines were studied. It is shown that the most effective strategy consists in the construction of the azoloazine core followed by halogenation with N-iodo- or N-bromosuccinimide. A series of 3-halopyrazolo[1,5-a]pyrimidines, which are bioisosteric analogs of natural purine nucleic bases and the drug Triazavirin®, were synthesized using this strategy. The obtained compounds are interesting as precursors of novel C-nucleosides, which can be synthesized by C-C-coupling with (pseudo)ribosides containing a keto group.

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References

  1. D. A. Gruzdev, V. V. Musiyak, G. L. Levit, V. P. Krasnov, V. N. Charushin, Russ. Chem. Rev., 2018, 87, 604; DOI: https://doi.org/10.1070/RCR4772.

    Article  CAS  Google Scholar 

  2. T. K. Warren, R. Jordan, M. K. Lo, A. S. Ray, R. L. Mackman, V. Soloveva, D. Siegel, M. Perron, R. Bannister, H. C. Hui, N. Larson, R. Strickley, J. Wells, K. S. Stuthman, S. A. Van Tongeren, N. L. Garza, G. Donnelly, A. C. Shurtleff, C. J. Retterer, D. Gharaibeh, R. Zamani, T. Kenny, B. P. Eaton, E. Grimes, L. S. Welch, L. Gomba, C. L. Wilhelmsen, D. K. Nichols, J. E. Nuss, E. R. Nagle, J. R. Kugelman, G. Palacios, E. Doerffler, S. Neville, E. Carra, M. O. Clarke, L. Zhang, W. Lew, B. Ross, Q. Wang, K. Chun, L. Wolfe, D. Babusis, Y. Park, K. M. Stray, I. Trancheva, J. Y. Feng, O. Barauskas, Y. Xu, P. Wong, M. R. Braun, M. Flint, L. K. McMullan, S. S. Chen, R. Fearns, S. Swaminathan, D. L. Mayers, C. F. Spiropoulou, W. A. Lee, S. T. Nichol, T. Cihlar, S. Bavari, Nature (London), 2016, 531, 381; DOI: https://doi.org/10.1038/nature17180.

    Article  CAS  PubMed  Google Scholar 

  3. E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, Russ. Chem. Bull., 2019, 68, 2172; DOI: https://doi.org/10.1007/S11172-019-2686-X.

    Article  CAS  Google Scholar 

  4. D. Ramesh, B. G. Vjjayakumar, T. Kannan, ChemMedChem., 2021, 16, 1403; DOI: https://doi.org/10.1002/CMDC.202000849.

    Article  CAS  PubMed  Google Scholar 

  5. M. Guinan, C. Benckendorff, M. Smith, G. J. Miller, Molecules, 2020, 25, 2050; DOI: https://doi.org/10.3390/MOLECULES25092050.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. E. S. Matyugina, S. N. Kochetkov, A. L. Khandazhinskaya, Russ. Chem. Rev., 2021, 90, 1454; DOI: https://doi.org/10.1070/RCR5013.

    Article  Google Scholar 

  7. R. A. Drokin, E. A. Fesenko, P. N. Mozharovskaia, M. V. Medvedeva, T. S. Svalova, A. N. Kozitsina, Ya. L. Esaulkova, A. S. Volobueva, V. V. Zarubaev, V. L. Rusinov, Russ. Chem. Bull., 2022, 71, 2460; DOI: https://doi.org/10.1007/S11172-022-3674-0.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. F. Z. Valdés, V. Z. Luna, B. R. Arévalo, N. V. Brown, M. C. Gutiérrez, Mini-Rev. Med. Chem., 2018, 18, 1684; DOI: https://doi.org/10.2174/1389557518666180516163539.

    Article  PubMed  PubMed Central  Google Scholar 

  9. K. V. Savateev, A. A. Spasov, V. L. Rusinov, Russ. Chem. Rev., 2022, 91, RCR5041; DOI: https://doi.org/10.1070/RCR5041.

    Article  Google Scholar 

  10. H. Wójtowicz-Rajchel, J. Fluor. Chem., 2012, 143, 11; DOI: https://doi.org/10.1016/J.JFLUCHEM.2012.06.026.

    Article  Google Scholar 

  11. K. V. Savateev, V. V. Fedotov, P. A. Slepukhin, E. N. Ulomsky, V. L. Rusinov, New J. Chem., 2022, 46, 17145; DOI: https://doi.org/10.1039/D2NJ03002K.

    Article  CAS  Google Scholar 

  12. J. Boryski, Nucleosides Nucleotides Nucleic Acid, 2006, 15, 771; DOI: https://doi.org/10.1080/07328319608002422.

    Article  Google Scholar 

  13. K. V. Savateev, V. V. Fedotov, E. N. Ulomsky, V. L. Rusinov, Chem. Heterocycl. Compd., 2018, 54, 197. DOI: https://doi.org/10.1007/s10593-018-2254-6.

    Article  CAS  Google Scholar 

  14. Q. Wu, C. Simons, Synthesis, 2004, 10, 1533; DOI: https://doi.org/10.1055/S-2004-829106.

    Article  Google Scholar 

  15. P. Merino, T. Tejero, E. Marca, F. Gomollón-Bel, I. Delso, R. Matute, Heterocycles, 2012, 86, 791; DOI: https://doi.org/10.3987/REV-12-SR(N)3.

    Article  CAS  Google Scholar 

  16. K. Temburnikar, K. L. Seley-Radtke, Beilstein J. Org. Chem., 2018, 14, 772; DOI: https://doi.org/10.3762/BJOC.14.65.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. R. T. Eastman, J. S. Roth, K. R. Brimacombe, A. Simeonov, M. Shen, S. Patnaik, M. D. Hall, ACS Cent. Sci., 2020, 6, 672; DOI: https://doi.org/10.1021/ACSCENTSCI.0C00489.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. R. Taylor, P. Kotian, T. Warren, R. Panchal, S. Bavari, J. Julander, S. Dobo, A. Rose, Y. El-Kattan, B. Taubenheim, Y. Babu, W. P. Sheridan, J. Infect. Public Health, 2016, 9, 220; DOI: https://doi.org/10.1016/J.JIPH.2016.04.002.

    Article  PubMed  PubMed Central  Google Scholar 

  19. K. S. Ramasamy, R. Bandaru, D. Averett, J. Org. Chem., 2000, 65, 5849; DOI: https://doi.org/10.1021/JO000460A.

    Article  CAS  PubMed  Google Scholar 

  20. B. M. Trost, L. S. Kallander, J. Org. Chem., 1999, 64, 5427; DOI: https://doi.org/10.1021/JO990195X.

    Article  CAS  PubMed  Google Scholar 

  21. J. Zhou, M. Yang, S. W. Schneller, Tetrahedron Lett., 2004, 45, 8233; DOI: https://doi.org/10.1016/J.TETLET.2004.09.007.

    Article  CAS  Google Scholar 

  22. X. Chen, S. W. Schneller, S. Ikeda, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, J. Med. Chem., 1993, 36, 3727; DOI: https://doi.org/10.1021/JM00075A030.

    Article  CAS  PubMed  Google Scholar 

  23. V. L. Rusinov, E. N. Ulomskii, O. N. Chupakhin, V. N. Charushin, Russ. Chem. Bull., 2008, 57, 985; DOI: https://doi.org/10.1007/S11172-008-0130-8.

    Article  CAS  Google Scholar 

  24. V. L. Rusinov, I. M. Sapozhnikova, A. A. Spasov, O. N. Chupakhin, Russ. Chem. Bull., 2022, 71, 2561; DOI: https://doi.org/10.1007/S11172-022-3687-8.

    Article  CAS  Google Scholar 

  25. V. L. Rusinov, O. N. Chupakhin, S. L. Deev, T. S. Shestakova, E. N. Ulomskii, L. I. Rusinova, O. I. Kiselev, E. G. Deeva, Russ. Chem. Bull., 2010, 59, 136; DOI: https://doi.org/10.1007/S11172-010-0056-9.

    Article  CAS  Google Scholar 

  26. Pat. RF 2294936 C1; Byul. Isobret. [Inventor Bull.], 2007, № 7 (in Russian).

  27. Pat. RF 2529487 C1; Byul. Isobret. [Inventor Bull.], 2014, № 27 (in Russian).

  28. E. M. Mukhin, K. V. Savateev, V. L. Rusinov, Russ. Chem. Bull., 2023, 72, 425; DOI: https://doi.org/10.1007/s11172-023-3810-1.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. O. N. Chupakhin, V. L. Rusinov, M. V. Varaksin, E. N. Ulomskiy, K. V. Savateev, I. I. Butorin, W. Du, Z. Sun, V. N. Charushin, Int. J. Mol. Sci., 2022, 23, 14537; DOI: https://doi.org/10.3390/IJMS232314537.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. V. L. Rusinov, V. N. Charushin, O. N. Chupakhin, Russ. Chem. Bull., 2018, 67, 573; DOI: https://doi.org/10.1007/S11172-018-2113-8.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    E. M. Mukhin, K. V. Savateev, E. K. Voinkov, E. N. Ulomsky & V. L. Rusinov

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  1. E. M. Mukhin
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  2. K. V. Savateev
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  3. E. K. Voinkov
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  4. E. N. Ulomsky
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  5. V. L. Rusinov
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Correspondence to E. M. Mukhin.

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Additional information

This work was performed under financial support of the Russian Science Foundation (Project No. 22-23-00282).

No human or animal subjects were used in this research.

Based on the materials of the VI International Scientific and Practical Conference “Modern Synthetic Methodologies for Creating Drugs and Functional Materials” (MOSM 2022) (November 7–11, 2022, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1821–1836, August, 2023.

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Mukhin, E.M., Savateev, K.V., Voinkov, E.K. et al. 3-Halopyrazolo[1,5-a]pyrimidines as promising precursors of novel C-nucleosides. Russ Chem Bull 72, 1821–1836 (2023). https://doi.org/10.1007/s11172-023-3965-0

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  • DOI: https://doi.org/10.1007/s11172-023-3965-0

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