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

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.

• Authors: R M Kondratenko, L A Baltina, S R Mustafina, E V Vasil'eva, R Pompei, D Deidda, O A Pliasunova, A G Pokrovskiĭ, G A Tolstikov
• Journal: Bioorganicheskaia khimiia (Bioorg Khim) 2004 May-Jun Vol. 30 Issue 3 Pg. 308-15 ISSN: 0132-3423 [Print] Russia (Federation)
• Vernacular Title: Sintez kon''iugatov glitsirrizinovoĭ kisloty s al'fa-D-gliukozaminom i nekotorymi glikozilaminami i ikh protivovirusnaia aktivnost'.
• PMID: 15344661 (Publication Type: Journal Article)

Chemical References

• Antiviral Agents
• Glycoconjugates
• Glycyrrhizic Acid
• Glucosamine

Topics

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