Synthesis and antiviral activity of novel glycyrrhizic acid conjugates with D-amino acid esters

A I Fayrushina; L A Baltina Jr; L A Baltina; N I Konovalova; P A Petrova; M Yu Eropkin

doi:10.1134/S1068162017040045

Synthesis and antiviral activity of novel glycyrrhizic acid conjugates with D-amino acid esters

Russ J Bioorg Chem. 2017;43(4):456-462. doi: 10.1134/S1068162017040045. Epub 2017 Aug 2.

Authors

A I Fayrushina¹, L A Baltina Jr¹, L A Baltina¹, N I Konovalova², P A Petrova², M Yu Eropkin²

Affiliations

¹ 1Ufa Institute of Chemistry, Russian Academy of Sciences, Ufa, 450054 Russia.
² 2Research Institute of Influenza, Ministry of Healthcare of the Russian Federation, St. Petersburg, 197376 Russia.

Abstract

Glycyrrhizic acid (GA) conjugates with methyl and ethyl esters of D-amino acids (D-Trp, D-Phe, D-Tyr, D-Val, D-Leu) have been synthesized by the activated esters method using mixtures of N-hydroxybenzotriazole or N-hydroxysuccinimide with N,N'-dicyclohexylcarbodiimide. GA conjugate with D-Trp ethyl ester exhibited antiviral activity against influenza viruses A/H3N2, A/H1N1/pdm09, A/H5N1, B (SI > 10-29), and HRSV (SI > 25). GA conjugate with D-Trp methyl ester inhibited influenza virus A/H1N1/pdm09 (SI > 30).

Keywords: amino acids; antiviral activity; conjugates; glycyrrhizic acid.