Transformation of glycyrrhizic acid. VII. Synthesis of triterpene glycopeptides containing alkyl esters of L-amino acids

Балтина, Л. А.; Ryzhova, S. A.; Васильева, Е. В.; Толстиков, Г. А.

doi:10.1007/bf00630013

Cited by 3 publications

(13 citation statements)

References 2 publications

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“…Several derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) of GL were used for screening of anti-SARS-CoV activity. The GL conjugate 1 of 2-acetamido-β-D-glucopyranosylamine was synthesized by the coupling reaction of GL and N-acetyl-β-Dglycopyranosylamine as described previously.…”

Section: Chemistrymentioning

confidence: 99%

“…12 Amino acid derivatives 2-8 of GL (glycopeptides) were synthesized by using N,N′-dicyclohexylcarbodiimide (DCC) and N-hydroxysuccinimide (HOSu) or DCC-N-hydroxybenzotriazole (HOBt) as previously reported. [13][14][15][16] The selective synthesis of compounds 2 and 3 containing two residues of S-benzyl-L-cysteine or glycyl-L-leucine in the carbohydrate part of the GL molecule was carried out by the activated ester method (DCC-HOSu) using S-benzyl-L-cysteine or glycyl-L-valine tert-butyl esters as hydrochlorides in tetrahydrofuran (THF) in the presence of Et 3 N. Glycopeptides 4 and 5 were prepared from GL and L-leucine tert-butyl or L-glutamic acid dibenzyl ester hydrochlorides by using DCC-HOBt in dioxane. 13,16 tert-Butyl ester groups were deblocked with CF 3 COOH, and benzyl ester groups were removed by catalytic hydrogenolysis over 10% Pd/C in 75% CH 3 -COOH.…”

Section: Chemistrymentioning

confidence: 99%

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Antiviral Activity of Glycyrrhizic Acid Derivatives against SARS−Coronavirus

et al. 2005

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Glycyrrhizin (GL) was shown to inhibit SARS-coronavirus (SARS-CoV) replication in vitro. Here the anti-SARS-CoV activity of 15 GL derivatives was tested. The introduction of 2-acetamido-beta-d-glucopyranosylamine into the glycoside chain of GL resulted in 10-fold increased anti-SARS-CoV activity compared to GL. Amides of GL and conjugates of GL with two amino acid residues and a free 30-COOH function presented up to 70-fold increased activity against SARS-CoV but also increased cytotoxicity resulting in decreased selectivity index.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Antiviral Activity of Glycyrrhizic Acid Derivatives against SARS−Coronavirus

et al. 2005

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“…GA (I) carboxyl groups were activated with hydroxybenzotriazol (HOBt) or N-hydrosuccinimide (HONSu) and N,N'-dicyclohexylcarbodiimide (DCC) [9,10]. Treatment of GA (I) with HOBt/DCC at GA-HOBt-DCC molar ratio 1 : 3.5 : 3.2 or HONSu/DCC at GA-HOSu-DCC molar ratio 1 : 5.2 : 3.2 in tetrahydrofuran/dioxane at 20-22°C resulted in activated tris(oxybenzotriazol) (II) and tris(oxysuccinimide) (III) esters and N,N'-dicyclohexylurea precipitate.…”

Section: Resultsmentioning

confidence: 99%

“…EXPERIMENTAL 1 H and 13 C NMR spectra were registered on an Avance-III (Brüker, Germany) pulse spectrometer at a working frequency of 500.13 ( 1 H) and 125.47 ( 13 C) MHz and an AVX-300 (Brüker) spectrometer at working frequencies of 300 and 75.5 MHz (δ, ppm; spinspin coupling constant, Hz); internal standard, tetramethylsilane. NMR spectral signals were referenced under common mode using the ACD LABS software package and literature data for GA and its amino acid conjugates [6,[9][10][11]. IR spectra were recorded on a Prestige-21 (Shimadzu, Japan) IR spectrophotometer in a paste with paraffin oil.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2017

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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).

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“…The synthesis of glycopeptides (89-140) was carried out by the condensation of GL (1) with alkyl (methyl, ethyl, propyl, butyl, tert-butyl) or benzyl (4-nitrobenzyl) esters of L-amino acids and dipeptides as hydrochlorides, tosylates and benzolsulphonates using an activated esters method, Nhydroxysuccinimide (HOSu) -DCC or Nhydroxybenzotriazole (HOBt)-DCC, in the presence of small excess (1-3 mmol) of triethylamine (Et 3 N) or Nmethylmorpholine (NMM) [76][77][78][79][80]. The yield of carboxyl protected glycopeptides was higher (80-95 %) when HOBt-DCC has been used for the activation of COOH-groups of GL [78][79][80].…”

Section: Synthesis Of Glycyrrhizic Acid Glycopeptidesmentioning

confidence: 99%

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Балтина

2003

CMC

219

159

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Glycyrrhizic Acid (GL) is the major bioactive triterpene glycoside of licorice root (Glycyrrhiza Radix) extracts possessing a wide range of pharmacological properties (anti-inflammatory, anti-ulcer, anti-allergic, anti-dote, anti-oxidant, anti-tumor, anti-viral etc.). Official sources of GL are Glycyrrhiza glabra L. and Gl. uralensis Fish. (Leguminosae). The content of GL in licorice root is 2-24% of the dry weight. GL is one of the leading natural compounds for clinical trials of chronic active viral hepatitis and HIV infections (preparation Stronger Neo-Minophagen C, SNMC), and its monoammonium salt (glycyram, tussilinar) is used as an anti-inflammatory and anti-allergic remedy. The synthetic transformations of GL on carboxyl and hydroxyl groups were carried out to produce new bioactive derivatives for medicine. GL esters were produced containing fragments of bioactive acids (4-nitrobenzoic, cinnamic, salycilic, acetylsalycilic, nicotinic, isonicotinic). Bioactive amides of GL were synthesized using chloroanhydride technique and N,N'-diciclohexylcarbodiimide (DCC) method. The synthesis of acylthioureids and semicarbazones was carried out via the reaction of triacylisothiocianate of penta-O-acetyl-GL with primary amines and hydrazines. The chain of transformations of trichloranhydride of penta-O-acetyl-GL was made with the introduction of diazoketone groups in the molecule. A new group of GL derivatives to be triterpene glycopeptides was prepared by the activated esters method (N-hydrohysuccinimide-DCC or N-hydroxybenzotriazol-DCC) using alkyl (methyl, ethyl, propyl, butyl, tert-butyl) or benzyl (4-nitrobenzyl) esters of amino acids. The glycyrrhizyl analogs of the known immunostimulator, N-acetyl-muramoyldipeptide (MDP), were synthesized using Reagent Woodward K. A series of ureids and carbamates of GL was synthesized containing 5-amino-5-desoxy-D-xylopyranose units. The synthesis of 4-nitro-4-desoxy-glycosides, modified analogs of GL, was carried out by the oxidative splitting of the carbohydrate part of GL with NaIO(4). Triterpene 2-desoxy-D-glycosides, analogs of GL, were prepared by the glycal method in the presence of iodine-containing promoters or sulfonic acid cation-exchange resin KU-2-8 (H+) and LiBr. New anti-inflammatory and anti-ulcer agents were found among GL derivatives such as esters, amides, ureids, carbamates, thioureids and glycopeptides. GL glycopeptides are of interest as immunomodulators. Some of the chemically modified GL derivatives (salts, amides, glycopeptides) were potent HIV-1 and HIV-2 inhibitors in vitro. Preparation niglizin (penta-O-nicotinate of GL) was studied clinically as an anti-inflammatory agent and is of interest for studies as hepatoprotector and HIV inhibitor.

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Transformation of glycyrrhizic acid. VII. Synthesis of triterpene glycopeptides containing alkyl esters of L-amino acids

Cited by 3 publications

References 2 publications

Antiviral Activity of Glycyrrhizic Acid Derivatives against SARS−Coronavirus

Antiviral Activity of Glycyrrhizic Acid Derivatives against SARS−Coronavirus

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

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

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