Isomerization of glycyrrhizic acid. Antiulcer activity

Балтина, Л. А.; Serdyuk, N. G.; Флехтер, О. Б.; Krasnova, L.; Davydova, V. A.; Ismagilova, A. F.; Zarudii, F. S.; Толстиков, Г. А.

doi:10.1007/bf02333885

Cited by 8 publications

(7 citation statements)

References 4 publications

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“…It was not allergic, teratogenic or mutagenic, and did not change blood indexes and plasma enzymes activity when administered per os (7 mg/kg30 times) [99][100][101]. GL derivatives were low toxic compounds too (LD 50 = 800-8000 mg/kg per os) [63,[68][69][70][71][72][73]76].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

“…Triacylisocianate (67) reacted with primary amines forming appropriate triacylthioureids (68)(69)(70)(71), and with hydrazines formed acylthiocemicarbazides (72-77) (scheme 1) [73].…”

Section: Synthesis Of Acylthioureides and Semicarbazidesmentioning

confidence: 99%

“…Protected amides of GL (44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56) were synthesized by the reaction of penta-O-acetyl GL trichloride (43) with amines R N H 2 with 52-90% yields [68,69]. Heterocyclic and aromatic amides (57)(58)(59)(60)(61)(62)(63)(64)(65)(66) were prepared by the condensation of GL with bioactive amines, quinolines, uracils and sulfanylamides using DCC [70][71][72].…”

Section: Synthesis Of Glycyrrhizic Acid Amidesmentioning

confidence: 99%

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

Балтина

2003

CMC

224

160

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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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Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

“…Triacylisocianate (67) reacted with primary amines forming appropriate triacylthioureids (68)(69)(70)(71), and with hydrazines formed acylthiocemicarbazides (72-77) (scheme 1) [73].…”

Section: Synthesis Of Acylthioureides and Semicarbazidesmentioning

confidence: 99%

Section: Synthesis Of Glycyrrhizic Acid Amidesmentioning

confidence: 99%

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

Балтина

2003

CMC

224

160

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“…[16] Гли-цирризиновая кислота не устойчива к нагреванию. [17] Установлено, что при хранении некоторых лекарствен-ных форм с GC в них быстро уменьшается его содер-жание даже при комнатной температуре.…”

Section: Physico -Chemical Characteristic and Biological Activity Of unclassified

Physico-chemical characteristic and biological activity of the supramolecular complex of glycyram with b-cyclodextrin

Yakovishin¹,

Гришковец²,

Корж³

et al. 2015

MHC

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“…Compound I was prepared by alkaline isomerization of 18b-GA (92%) as described in [19], followed by purification as potassium salts by dissolution in acetone and precipitation of the 3K salt of I with 10% KOH/MeOH solution, conversion of 3K salts of I into monopotassium salts (II) by crystallization from glacial acetic acid, and recrystallization from aqueous ethanol. Treatment of purified salts II with the cation exchange resin KU-2-8 in the H + form in 85% EtOH yielded acid I with a purity of 85 ± 2% (HPLC data), which was used to prepare esters (III -VI).…”

mentioning

confidence: 99%

Synthesis and antiviral activity of 18α-glycyrrhizic acid and its esters

et al. 2010

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New esters (sulfate, nicotinates, and 4-methoxycinnamate) of 18a-glycyrrhizic acid (18a-GA) were synthesized; these were D/E-trans-isomers of natural 18b-GA (GA), which is the major triterpene glycoside in the roots of Spanish licorice and Urals licorice (Glycyrrhiza glabra L. and Gl. uralensis Fisher). Changes in the stereochemistry of the GA aglycone led to significant decreases in its anti-HIV-1 activity.

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Isomerization of glycyrrhizic acid. Antiulcer activity

Cited by 8 publications

References 4 publications

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

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

Physico-chemical characteristic and biological activity of the supramolecular complex of glycyram with b-cyclodextrin

Synthesis and antiviral activity of 18α-glycyrrhizic acid and its esters

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