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Bicyclic furano-, pyrrolo-, and thiopheno[2,3-d] derivatives of pyrimidine nucleosides: Synthesis and antiviral properties

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Abstract

The methods of synthesis of furano-, thiopheno-, and pyrrolo[2,3-d]pyrimidine deoxyribonucleosides and their derivatives and studies of the relationship between the structure and the antiviral activity of these compounds towards the viruses of varicella zoster, hepatitis C, and others have been reviewed.

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Abbreviations

BPN:

bicyclic pyrimidine nucleoside

BSA:

bis-N,O-trimethylsilylacetamide

BVDV:

bovine viral diarrhea virus

CC50 :

dose of the preparation that induces the death of 50% of uninfected cells

CMV:

cytomegalovirus

DBAD:

dibenzylazodicarboxylate

EC50 :

effective concentration required for the 50% inhibition of virus development

Fmoc:

9-fluorenylmethyloxycarbonyl

FPN:

furanopyrimidine nucleoside

HCV:

hepatitis C virus

HCMV:

human cytomegalovirus (human herpes virus type 5)

HMDS:

1,1,1,3,3,3-hexamethyldisilazane

HSV-1:

herpes virus type 1

HSV-2:

herpes virus type 2

IS:

index of selectivity (the CC50/EC50 ratio)

MCC:

minimal cytotoxic concentration inducing a marked change in cell morphology

Pd[PPh3]4 :

tetrakis(triphenylphosphine)palladium(0)

TK− VZV:

strain of varicella zoster virus deficient in thymidine kinase

TK+VZV:

strain of varicella zoster virus containing thymidine kinase

TMS-triflate:

trimethylsilyl trifluoromethanesulfonate

VV:

vaccinia virus

VZV:

varicella zoster virus

VZV TK:

thymidine kinase of VZV

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  1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991, Russia

    M. A. Ivanov & L. A. Aleksandrova

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  1. M. A. Ivanov
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Original Russian Text © M.A. Ivanov, L.A. Aleksandrova, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 1, pp. 26–45.

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Ivanov, M.A., Aleksandrova, L.A. Bicyclic furano-, pyrrolo-, and thiopheno[2,3-d] derivatives of pyrimidine nucleosides: Synthesis and antiviral properties. Russ J Bioorg Chem 39, 22–39 (2013). https://doi.org/10.1134/S1068162013010044

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