New Benzimidazole 3′-Deoxynucleosides: Synthesis and Antiherpes Virus Properties
2025
Aleksandra O. Arnautova | 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 | Valeria L. Andronova | Georgii A. Galegov | Maria A. Kostromina | Evgeny A. Zayats | Inna L. Karpenko | Svetlana K. Kotovskaya | Valery N. Charushin | Roman S. Esipov | Anatoly I. Miroshnikov | Irina D. Konstantinova
A series of new 3′-deoxyribosides of substituted benzimidazoles was obtained by the chemo-enzymatic method using genetically engineered <i>E. coli </i>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 (IC<sub>50</sub> = 250.92 µM, SI = 12.00) and 4,5,6-trifluoro-1-(β-D-3′-deoxyribofuranosyl)benzimidazole (IC<sub>50</sub> = 249.96 µM, SI = 16.00) showed significant selective activity against both viral models in comparison to ribavirin (IC<sub>50</sub> = 511.88 µM, SI > 8.00).
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