Synthesis and Anti-HIV-1 Activity of Olean-9(11),12(13)-Dien-30-Oic Acid 3β-(2-O-β-D-Glucuronopyranosyl-β-D-Glucuronopyranoside)

Балтина, Л. А.; Stolyarova, O. V.; Кондратенко, Р. М.; Gabbasov, T. M.; Plyasunova, O. A.; Ilina, Tatiana V.

doi:10.1007/s11094-014-1127-2

Cited by 4 publications

(1 citation statement)

References 13 publications

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“…GL conjugate with D-galactose amine (14) connected to the carbohydrate part of glycoside by CONH-bonds was synthesized as described before. 44 GL 1 and its derivatives and analogs 2-19 were evaluated for their inhibitory activity against pandemic influenza A/H1N1/ pdm09 virus in the MDCK cells. 42 Its derivatives (16,17) to be conjugates with methyl esters of L-aspartic acid were described previously.…”

Section: Introductionmentioning

confidence: 99%

Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors

Baltina

Zarubaev

Балтина

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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This Letter describes the synthesis and antiviral activity study of some glycyrrhizic acid (GL) derivatives against influenza A/H1N1/pdm09 virus in MDCK cells. Conjugation of GL with l-amino acids or their methyl esters, and amino sugar (d-galactose amine) dramatically changed its activity. The most active compounds were GL conjugates with aromatic amino acids methyl esters (phenylalanine and tyrosine) (SI=61 and 38), and S-benzyl-cysteine (SI=71). Thus modification of GL is a perspective route in the search of new antivirals, and some of GL derivatives are potent as anti-influenza A/H1N1 agents.

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Section: Introductionmentioning

confidence: 99%

Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors

Baltina

Zarubaev

Балтина

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Effect of Glycyrrhetic Acid Derivatives on Regulation of Thymocyte Volume

et al. 2023

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Synthesis of Glycyrrhizic Acid Conjugates with S-Benzyl-L-Cysteine and Their Antiviral Activity

2021

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A new method for the synthesis of glycyrrhizic acid (GA) conjugates with S-benzyl- L -cysteine using 1-ethyl-3-(3-dimethylaminoproopyl)carbodiimide is proposed. It is established that 3- O -{2- O -[ N -(β- D -glucopyranosyluronyl)- L -cysteine- S -benzyl]- N -(β- D -glucopyranosyluronyl)- L -cysteine- S -benzyl}-(3β,20β)-11-oxo-30-( N -carbonyl- L -cysteine- S -benzyl)-30-norolean-12-ene is superior to GA in inhibiting the accumulation of HIV-I virus-specific protein p24 (viral antigen) in MT-4 cell culture (IC 50 3 μg/mL, SI 90) and is 50 – 55 times less toxic to cells than azidothymidine.

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Synthesis and Anti-HIV-1 Activity of Olean-9(11),12(13)-Dien-30-Oic Acid 3β-(2-O-β-D-Glucuronopyranosyl-β-D-Glucuronopyranoside)

Cited by 4 publications

References 13 publications

Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors

Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors

Effect of Glycyrrhetic Acid Derivatives on Regulation of Thymocyte Volume

Synthesis of Glycyrrhizic Acid Conjugates with S-Benzyl-L-Cysteine and Their Antiviral Activity

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