[The synthesis and antiviral activity of glycyrrhizic acid conjugates with alpha-D-glucosamine and some glycosylamines]

Bioorg Khim. 2004 May-Jun;30(3):308-15. doi: 10.1023/b:rubi.0000030135.97089.37.
[Article in Russian]

Abstract

Glycyrrhizic acid and its 30-methyl ester were conjugated with 2-amino-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose, 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl amine, 2,3,4-tri-O-acetyl-apha-L-arabinopyranosyl amine, 2-acetamido-2-deoxy-beta-D-glucopyranosyl amine, and beta-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-beta-D-glucopyranosyl amine in the carbohydrate part of its molecule exhibited antiviral activity (ID50 4 microg/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 microg/ml. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 3; see also http://www.maik.ru.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cells, Cultured
  • Chlorocebus aethiops
  • Glucosamine / chemistry*
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Glycoconjugates / pharmacology*
  • Glycyrrhizic Acid / chemistry*
  • Simplexvirus / drug effects
  • Vero Cells

Substances

  • Antiviral Agents
  • Glycoconjugates
  • Glycyrrhizic Acid
  • Glucosamine