New Amino-Acid Conjugates of Glycyrrhizic Acid

Glycyrrhizic acid derivatives as Dengue virus inhibitors

“…Compounds (16,17) containing the residues of aspartic and 11-amino undecanoic acid methyl esters in the carbohydrate part of GL were produced by using Nhydroxysuccinimide (HOSu) and DCC. 34,35 The analytical and spectral data of GL derivatives 2-17 were identical to the literature data, the purity of compounds was monitored by thin layer chromatography and high pressure liquid chromatography (HPLC) (˃95% of purity) (in the Supplementary Material, Supplemental Figs. 1-3).…”

“…We concluded that this study was the first report to display structure-anti-DENV activity relationships of GL derivatives, revealing that the modification of GL by the conjugation with amino acids and the introduction of aromatic acyl hydrazide residues into the carbohydrate part strongly influenced on the antiviral activity of GL against DENV2. Among GL derivatives tested, GL compounds 13 32 and 17 35 have been identified as potent DENV2 inhibitors. Thus, the conjugation of GL derivatives with amino acids is a perspective way to produce potent DENV2 inhibitors.…”

New method of preparation of carboxy-protected amino acid conjugates of glycyrrhizinic acid

“…Earlier we showed that the conjugates of glycyrrhizinic acid with amino acids and dipeptides proved to be promising for medicine as anti-AIDS agents [9], inhibitors of Epstein-Barr virus [10], anti-SARS CoV-agents [11], inhibitors of influenza virus А/H1N1/pdm2009 [12], and as immunostimulators [13,14]. Various methods were developed for the preparation of amino acid conjugates of glycyrrhizinic acid with the use of N-hydroxybenzotriazole (HOBt) or the system N-hydroxysuccinimide-N,N'-dicyclohexylcarbodiimide and the complex of pentafluorophenol with N,N'-dicyclohexylcarbodiimide for the activation of carboxy group of glycoside [15][16][17][18].…”

Synthesis of amino acid conjugates of glycyrrhizic acid using N-hydroxyphthalimide and N,N'-dicyclohexylcarbodiimide

“…A number of conjugates of glycyrrhizic acid with amino acids and dipeptides possesses meaningful anti-AIDS-1 activity [6,7], and is of interest as anti-SARS CoV-agents [8] and inhibitors of Epstein-Barr virus [9]. It was found recently that some amino acid conjugates of glycyrrhizic acid possess significant virus inhibition activity towards pandemic influenza virus А/H1N1/pdm2009 [10,11]. Earlier we developed methods for the preparation of glycyrrhizic acid conjugates with alkyl and benzyl (4nitrobenzyl) esters of amino acids with the use of Nhydroxybenzotriazole (HOBt), N,N-dicyclohexylcarbodiimide (DCC), or N-hydroxysuccinimide (HOSu) that allowed synthesis of the derivatives of glycyrrhizic acid with two or three amino acid residues or their esters depending on the reaction conditions [4,5,12,13].…”