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Synthesis and Antiviral Activity of Glycyrrhizic-Acid Conjugates with Aromatic Amino Acids

Author:
Baltina, L.A., Jr, Fairushina, A.I., Baltina, L.A., Eropkin, M.Yu., Konovalova, N.I., Petrova, P.A., Eropkina, E.M.
Source:
Chemistry of natural compounds 2017 v.53 no.6 pp. 1096-1100
ISSN:
0009-3130
Subject:
antiviral properties, Human alphaherpesvirus 1, salts, glycyrrhizin, Orthomyxoviridae, tryptophan, tyrosine, triterpenoids, sodium, viruses, phenylalanine, herpes simplex
Abstract:
Amino-acid conjugates of glycyrrhizic acid (GA) containing phenylalanine, tyrosine, and tryptophan in the carbohydrate and triterpene parts were synthesized using N-hydroxybenzotriazole (HOBt)-N,N′-dicyclohexylcarbodiimide (DCC) and sodium salts of the amino acids. GA conjugates containing two aminoacid residues in the glycoside carbohydrate part were synthesized using N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The GA conjugate with tyrosine exhibited weak but consistent antiviral activity against flu virus A/St.-Petersburg/05/09 (H1N1)pdm09 that was similar to the standard strain A/California/07/09 and pronounced antiviral activity against respiratory-syncytial virus (RSV) and herpes simplex virus (HSV-1).
Agid:
5867251