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New nido-carborane-containing conjugates of purine: synthesis and antiviral activity

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Abstract

New purine derivatives containing a nido-carborane fragment were synthesized by nucleophilic substitution of chlorine atom in 6-chloropurine and 2-amino-6-chloropurine under the action of nido-carborane-containing amines. Compounds with significant activity against the acyclovir-resistant strain of herpes simplex virus type 1, as well as with moderate activity against influenza viruses A and B, were discovered for the first time among the synthesized nido-carboranyl derivatives of purine.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108, Ekaterinburg, Russian Federation

    D. A. Gruzdev, A. A. Telegina, G. L. Levit & V. P. Krasnov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    V. A. Ol’shevskaya

  3. D. I. Ivanovskiy Institute of Virology, N. F. Gamaleyi National Research Center for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, 16 ul. Gamaleyi, 123098, Moscow, Russian Federation

    V. L. Andronova & G. A. Galegov

  4. St. Petersburg Pasteur Institute of Epidemiology and Microbiology, 14 ul. Mira, 197101, St. Petersburg, Russian Federation

    V. V. Zarubaev

Authors
  1. D. A. Gruzdev
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  2. A. A. Telegina
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  3. V. A. Ol’shevskaya
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  4. V. L. Andronova
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  5. G. A. Galegov
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  6. V. V. Zarubaev
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  7. G. L. Levit
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  8. V. P. Krasnov
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Corresponding author

Correspondence to D. A. Gruzdev.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 21-73-10073 concerning synthesis of compounds and Project No. 19-13-00231-P concerning testing antiviral activity).

Equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” (CJU “SAOC”) at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch) (Ekaterinburg) was used.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the V Russian Conference on Medicinal Chemistry with international participation “MedChem-Russia 2021” (May 16–19, 2022, Volgograd, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2375–2382, November, 2022.

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Gruzdev, D.A., Telegina, A.A., Ol’shevskaya, V.A. et al. New nido-carborane-containing conjugates of purine: synthesis and antiviral activity. Russ Chem Bull 71, 2375–2382 (2022). https://doi.org/10.1007/s11172-022-3665-1

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