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Synthesis and antiherpetic activity of (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines

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Abstract

The isomeric (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines were synthesized. The stereoselectivity of double bond formation was studied by variation of sulfonyl groups. The resulting phosphonates exhibited a moderate antiherpetic activity in a culture of Vero cells infected with herpes simplex type 1 virus. The Z-isomer was shown to be a more effective inhibitor of virus reproduction in the case of both wild and acyclovir-resistant strains.

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Abbreviations

HSV-1/L2:

herpes simplex virus type 1 strain L2

HSV-1/L2/R:

acyclovir-resistant herpes simplex virus type 1 strain L2

ID50 and ID95 :

doses inhibiting virus cytopathogenic activity by 50 and 95%, respectively

IMP:

ethyl iodometylphosphonate

Ms:

mesyl (methanesulfonyl)

PMEA:

9-(2-phospho-nomethoxyethyl)adenine

SI:

selectivity index (the TCD50: ID50 ratio)

TBDMS:

tert-butyldimethylsilyl

TCD50 :

tissue cytotoxicity dose responsible for the change in 50% of cell monolayer

Tr:

trityl (triphenylmethyl)

Ts:

tosyl (p-toluenesulfonyl).

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Authors and Affiliations

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

    A. V. Ivanov & M. V. Jasko

  2. Ivanovskii Institute of Virology, Russian Academy of Medical Sciences, ul. Gamalei 16, 123098, Moscow, Russia

    V. L. Andronova & G. A. Galegov

Authors
  1. A. V. Ivanov
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  2. V. L. Andronova
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  3. G. A. Galegov
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  4. M. V. Jasko
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Correspondence to A. V. Ivanov.

Additional information

Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 1, 2005, pp. 65–72.

Original Russian Text Copyright © 2005 by Ivanov, Andronova, Galegov, Jasko.

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Ivanov, A.V., Andronova, V.L., Galegov, G.A. et al. Synthesis and antiherpetic activity of (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines. Russ J Bioorg Chem 31, 58–65 (2005). https://doi.org/10.1007/s11171-005-0007-7

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  • DOI: https://doi.org/10.1007/s11171-005-0007-7

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