Novel amides of pentaacetylglycyrrhizic acid and their antiinflammatory activity

Балтина, Л. А.; Davydova, V. A.; Толстикова, Т. Г.; Zarudii, F. S.; Кондратенко, Р. М.; Насыров, Х. М.; Lazareva, D. N.; Толстиков, Г. А.

doi:10.1007/bf00764436

Cited by 1 publication

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“…Some amides of GL were more potent and less toxic (LD 50 5000-8000 mg/kg) anti-inflammatory agents as compared to prednizolone in the carrageenan-induced inflammation of mice [68,69]. The anti-inflammatory activity of heterocyclic amides (58,59) was more expressed than that of GL in the carrageenan-induced inflammation on 50 mg/kg dose.…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

“…Potent anti-inflammatory agents were found among GL esters, amides, glycopeptides and ureides [68][69][70][103][104][105][106]. The anti-inflammatory activity of penta-O-cinnamate (34) and penta-O-(4-nitro)benzoate (27) was more pronounced in the carrageenan and formaldehyde induced models of inflammation in mice, than that of GL [103].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

“…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%

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

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%