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Балтина, Л. А.; Кондратенко, Р. М.; Мустафина, С. Р.; Флехтер, О. Б.; Murinov, Yu. I.; Davydova, V. A.; Zarudii, F. S.; Ismagilova, A. F.; Толстиков, Г. А.

doi:10.1023/a:1010454810888

Cited by 9 publications

(10 citation statements)

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“…The anti-inflammatory activity of GL and its derivatives was combined with the expressed antiulcer properties. 18β-GL and its salts exhibited high antiulcer activities on 100 mg/kg doses in various pathogenic models of experimental destructions of the rat's stomach mucous membrane caused by indomethacin, voltaren, cinchophen and acetylsalycilic acid; this effect was similar to the effect of carbenoxolone (100 mg/kg) and cimetidine (200 mg/kg), which are a well-known antagonists of H 2 -receptors of histamine [53,62]. Monosodium and mixed potassiumdilithium salts showed the most expressed anti-ulcer activity and were more active as compared to GL and cimetidine [62].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 82%

“…Purified GL (92±2%) was produced from commercial monoammonium salt (75±2% purity) using 1. 5% aqueous H2SO4, acetone and 10% solution of KOH in methanol for the precipitation of glycoside [53]. Crystalline high purity GL (97±2%) was received when sulfonic acid cation-exchange resins (KU-2, KU-2-8, Dowex-50, Amberlite IR-120) in H + -form were used instead of H 2 SO 4 [54].…”

Section: Isolation Of Glycyrrhizic Acid From Raw Materials and Its Stmentioning

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%

“…Oleanane type 3-O-2-deoxy-α-glycosides (194)(195)(196) were synthesized firstly in our laboratory via stereoselective glycosylation of methyl esters of 18β-and 18α-GLA, 11-desoxo-GLA and 18,19-dehydro-GLA with glycals acetates in the presence of iodine-containing activators such as N-iodsuccinimide (NIS) [89][90][91] and iodonium dicollidine perchlorate (IDCP) [92][93][94] ii i + ROH i ii yielded 2-deoxy-α-D-arabino-and lyxo-hexopyranosides of 18β-, 18α-GLA, and 11-deoxo-GLA as modified analogs of the natural glycoside, GL (1) [89][90][91]. When IDCP was used as a promoter of glycosylation the yield of the intermediate 2-deoxy-2-iodohexopyranosides was increased by approximately 20% as compared to the NIS method [92][93][94]. 2,6-dideoxy-α-L-arabino-hexopyranosides of 18β-, 18α-GLA, and 11-desoxo--GLA (196,199) were synthesized using di-O-acetyl-L-rhamnal and IDCP [91,94].…”

Section: Stereoselective Synthesis Of Triterpene 2-desoxy--glycosidesmentioning

confidence: 99%

“…Triterpene 2-deoxy-α-glycosides were also synthesized stereoselectively by the glycosylation of triterpene alcohols with acetylated glycals in the presence of sulfonic acid cation-exchange resin KU-2-8 (H + ) and LiBr [95][96][97]. This method improved the yield of target products and shortened the synthetic pathway.…”

Section: Stereoselective Synthesis Of Triterpene 2-desoxy--glycosidesmentioning

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: 82%

Section: Isolation Of Glycyrrhizic Acid From Raw Materials and Its Stmentioning

confidence: 99%