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Biomolecules
Volume 15
Issue 7
10.3390/biom15070922
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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

New Benzimidazole 3′-Deoxynucleosides: Synthesis and Antiherpes Virus Properties

by
Aleksandra O. Arnautova
1,2,*,
Irina A. Aleksakhina
1,
Ekaterina A. Zorina
1,
Maria Ya. Berzina
1,
Ilya V. Fateev
1,
Barbara Z. Eletskaya
1,
Konstantin V. Antonov
1,
Olga S. Smirnova
1,
Alexander S. Paramonov
1,
Alexey L. Kayushin
1,
Valeria L. Andronova
3,
Georgii A. Galegov
3,
Maria A. Kostromina
1,
Evgeny A. Zayats
1,
Inna L. Karpenko
2,
Svetlana K. Kotovskaya
4,5,
Valery N. Charushin
4,5,
Roman S. Esipov
1,
Anatoly I. Miroshnikov
1 and
Irina D. Konstantinova
1,*
1
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16/10, 119991 Moscow, Russia
2
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova St. 32, 119991 Moscow, Russia
3
Ivanovsky Institute of Virology, Gamaleya National Research Center for Epidemiology, Ministry of Healthcare of the Russian Federation, Gamaleya St. 18, 123098 Moscow, Russia
4
Postovsky Institute of Organic Synthesis, The Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya/Academicheskaya St. 22/20, 620041 Ekaterinburg, Russia
5
Department of Organic and Biomolecular Chemistry, Yeltsin Ural Federal University, N., Mira St. 19, 620002 Ekaterinburg, Russia
*
Authors to whom correspondence should be addressed.
Biomolecules 2025, 15(7), 922; https://doi.org/10.3390/biom15070922
Submission received: 25 April 2025 / Revised: 15 June 2025 / Accepted: 19 June 2025 / Published: 23 June 2025
(This article belongs to the Special Issue Chemical Biology and Biotechnology of Nucleosides, Nucleotides, and Nucleic Acids)
Versions Notes

Abstract

A series of new 3′-deoxyribosides of substituted benzimidazoles was obtained by the chemo-enzymatic method using genetically engineered E. coli purine nucleoside phosphorylase (PNP). In the case of asymmetrically substituted benzimidazole derivatives, a mixture of N1- and N3-regioisomers was formed (confirmed by NMR). The antiviral activity of the obtained compounds against herpes simplex virus 1 of reference strain L2 and a strain deeply resistant to acyclovir in Vero E6 cell culture was studied. 4,6-Difluoro-1-(β-D-3′-deoxyribofuranosyl)benzimidazole (IC50 = 250.92 µM, SI = 12.00) and 4,5,6-trifluoro-1-(β-D-3′-deoxyribofuranosyl)benzimidazole (IC50 = 249.96 µM, SI = 16.00) showed significant selective activity against both viral models in comparison to ribavirin (IC50 = 511.88 µM, SI > 8.00).
Keywords: nucleosides; fluorinated benzimidazoles; transglycosylation reaction; purine nucleoside phosphorylase; herpes simplex virus; 3′-deoxyribonucleosides nucleosides; fluorinated benzimidazoles; transglycosylation reaction; purine nucleoside phosphorylase; herpes simplex virus; 3′-deoxyribonucleosides

Share and Cite

MDPI and ACS Style

Arnautova, A.O.; Aleksakhina, I.A.; Zorina, E.A.; Berzina, M.Y.; Fateev, I.V.; Eletskaya, B.Z.; Antonov, K.V.; Smirnova, O.S.; Paramonov, A.S.; Kayushin, A.L.; et al. New Benzimidazole 3′-Deoxynucleosides: Synthesis and Antiherpes Virus Properties. Biomolecules 2025, 15, 922. https://doi.org/10.3390/biom15070922

AMA Style

Arnautova AO, Aleksakhina IA, Zorina EA, Berzina MY, Fateev IV, Eletskaya BZ, Antonov KV, Smirnova OS, Paramonov AS, Kayushin AL, et al. New Benzimidazole 3′-Deoxynucleosides: Synthesis and Antiherpes Virus Properties. Biomolecules. 2025; 15(7):922. https://doi.org/10.3390/biom15070922

Chicago/Turabian Style

Arnautova, Aleksandra O., Irina A. Aleksakhina, Ekaterina A. Zorina, Maria Ya. Berzina, Ilya V. Fateev, Barbara Z. Eletskaya, Konstantin V. Antonov, Olga S. Smirnova, Alexander S. Paramonov, Alexey L. Kayushin, and et al. 2025. "New Benzimidazole 3′-Deoxynucleosides: Synthesis and Antiherpes Virus Properties" Biomolecules 15, no. 7: 922. https://doi.org/10.3390/biom15070922

APA Style

Arnautova, A. O., Aleksakhina, I. A., Zorina, E. A., Berzina, M. Y., Fateev, I. V., Eletskaya, B. Z., Antonov, K. V., Smirnova, O. S., Paramonov, A. S., Kayushin, A. L., Andronova, V. L., Galegov, G. A., Kostromina, M. A., Zayats, E. A., Karpenko, I. L., Kotovskaya, S. K., Charushin, V. N., Esipov, R. S., Miroshnikov, A. I., & Konstantinova, I. D. (2025). New Benzimidazole 3′-Deoxynucleosides: Synthesis and Antiherpes Virus Properties. Biomolecules, 15(7), 922. https://doi.org/10.3390/biom15070922

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