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The Synthesis and Antiviral Activity of Glycyrrhizic Acid Conjugates with α-D-Glucosamine and Some Glycosylamines

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Abstract

Glycyrrhizic acid and its 30-methyl ester were conjugated with 2-amino-1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranose, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl amine, 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl amine, 2-acetamido-2-deoxy-β-D-glucopyranosyl amine, and β-D-galactopyranosyl amine using N,N′-dicyclohexylcarbodiimide and its mixtures with N-hydroxybenzotriazole. Structures of the conjugates were confirmed by IR, UV, 1H, and 13C NMR spectroscopy. The glycoconjugate with the residues of 2-acetamido-2-deoxy-β-D-glucopyranosyl amine in the carbohydrate part of its molecule exhibited antiviral activity (ID50 4 μg/ml) toward the herpes simplex type 1 virus (HSV-1) in the VERO cell culture. Two compounds demonstrated anti-HIV-1 activity (50–70% inhibition of p24) in a culture of MT-4 cells at concentrations of 0.5–20 μg/ml.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia

    R. M. Kondratenko, L. A. Baltina, S. R. Mustafina, E. V. Vasil'eva & G. A. Tolstikov

  2. Department of Medical Sciences, University of Cagliari, Italy

    R. Pompei & D. Deidda

  3. Vector State Scientific Center of Virusology and Biotechnology, pos. Koltsovo, Novosibirsk oblast, 633159, Russia

    O. A. Plyasunova & A. G. Pokrovskii

Authors
  1. R. M. Kondratenko
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  2. L. A. Baltina
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  3. S. R. Mustafina
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  4. E. V. Vasil'eva
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  5. R. Pompei
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  6. D. Deidda
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  7. O. A. Plyasunova
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  8. A. G. Pokrovskii
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  9. G. A. Tolstikov
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Corresponding author

Correspondence to L. A. Baltina.

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Kondratenko, R.M., Baltina, L.A., Mustafina, S.R. et al. The Synthesis and Antiviral Activity of Glycyrrhizic Acid Conjugates with α-D-Glucosamine and Some Glycosylamines. Russian Journal of Bioorganic Chemistry 30, 275–282 (2004). https://doi.org/10.1023/B:RUBI.0000030135.97089.37

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  • DOI: https://doi.org/10.1023/B:RUBI.0000030135.97089.37

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