The Synthesis and Antiviral Activity of Glycyrrhizic Acid Conjugates with α-D-Glucosamine and Some Glycosylamines

Кондратенко, Р. М.; Балтина, Л. А.; Мустафина, С. Р.; Васильева, Е. В.; Pompei, Raffaello; Deidda, Delia; Плясунова, О. А.; Покровский, А. Г.; Толстиков, Г. А.

doi:10.1023/b:rubi.0000030135.97089.37

Cited by 12 publications

(14 citation statements)

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“…There are signals of free 30-COOH at 180.3-180.8 ppm as in the 13 C NMR GA. 37 Analytical and spectral data for new compounds 5-7 are given in the References and notes. 41 Stereo isomeric 18a-GL (15) was produced by the alkaline isomerization of GL according to method. 23,31 Compounds (11) and (13) containing free amino acids have been synthesized previously by using HOSu-DCC and S-benzyl(Bn)-cysteine-or N e -carbobenzoxy(Z)lysine tert-butyl esters hydrochlorides.…”

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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“…Some of these new compounds exhibited promising selectivity indices (Kondratenko et al 2004(Kondratenko et al , 2009.…”

Section: Oleananesmentioning

confidence: 99%

Anti-HIV activity of natural triterpenoids and hemisynthetic derivatives 2004–2009

Cassels

Asencio²

2010

Phytochem Rev

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The continued advance of HIV-AIDS makes the development of relatively inexpensive, freely accessible, and mechanistically more diverse antiviral therapies an urgent need. Natural products are, directly or indirectly, an important potential source of compounds meeting these conditions. A review of the recent literature indicates that some hemisynthetic triterpenoid derivatives, particularly belonging to the lupane, oleanane and ursane series, may be nearing a stage where they can be used to complement existing therapeutic approaches. On the other hand, although some natural derivatives of tetracyclic terpenoid families have revealed many novel structures and some promise as anti-HIV substances, their chemical modification to improve their potency and selectivity remains practically untouched. While ongoing work with the more 'classical' pentacyclic triterpenoids will continue to be a fertile field for HIV-AIDS drug discovery, the other structural groups offer unprecedented opportunities for the development of additional substances with useful properties and for the discovery of novel targets for antiviral therapy.

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“…The free triterpene derivatives of D-glucosamine 2 and 4 were obtained in yields of 75-80%. The anomeric C-1′ of α-D-GlcN was observed in the spectra of 2 and 4 at weak field (90-92 ppm, α-anomers) [4].…”

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confidence: 95%

“…In continuation of studies on the synthesis of new bioactive derivatives and modified analogs of GA [4][5][6], we synthesized for the first time triterpene amides of α-D-glucosamine (α-D-GlcN) (1)(2)(3)(4). Methyl esters of 3β-O-carboxypropionyl-18β-and -18α-glycyrrhetic acids were used as the starting triterpenes [7].…”

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confidence: 99%