Antidotal and antiradical activity of complexes of β-glycyrrhizic acid with pyrimidine derivatives

Толстиков, Г. А.; Мышкин, В. А.; Балтина, Л. А.; Murinov, Yu. I.; Срубилин, Д. В.; Vakaritsa, A. F.; Алехин, Е. К.

doi:10.1007/bf02333971

Cited by 9 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…LD 50 of the purified GL (95%) was 5000 mg/kg per os in mice [98]. Toxicological studies of monoammonium salt of GL showed that it had no side-effects when administered in doses up to 700 mg/kg during 2 months or 90 mg/kg for 4 months in mice, rats and pigs [7].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

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

Балтина

2003

CMC

222

160

View full text Add to dashboard Cite

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.

show abstract

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

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

Балтина

2003

CMC

222

160

View full text Add to dashboard Cite

show abstract

“…Uracil derivatives are interesting molecules in the area of drug discovery 35 since they exhibit significant pharmacological applications as antiviral 36 , anticancer, cytotoxic 37 , antimycobacterial 38 , anti-inflammatory 39 , antitumor 34,40 , and antibacterial 41 . Moreover, some uracil derivatives showed antithrombotic 42 , antidotal 43 and potent inhibitors of interleukin-8-induced neutrophil chemotaxis 44 . Some uracils, particularly 6-aminouracils and their corresponding thiouracil derivatives, have been widely used as starting materials for the synthesis of a huge number of biologically important nitrogen-containing heterocycles [45][46][47][48] .…”

Section: Introductionmentioning

confidence: 99%

Aminouracil and aminothiouracil as versatile precursors for a variety of heterocyclic systems

Diab¹,

Salem²,

Abdelhamid³

et al. 2021

Arkivoc

View full text Add to dashboard Cite

Heterocycles, particularly pyrimidine derivatives, which are present in many natural products and many interesting synthetic compounds, are the most diverse class of organic compounds and have significant chemical, biomedical and industrial applications. Uracil, a pyrimidine derivative, constitutes a promising structure in widespread natural products and many of its derivatives exhibited significant pharmacological properties. They have been widely used as starting materials for the synthesis of a huge number of biologically important nitrogen-containing heterocycles. This review casts light on various methods for the construction of different heterocyclic systems utilizing aminouracil and aminothiouracil as versatile precursors. The heterocyclic systems mentioned in this review are categorized according to the type of the heterocyclic systems.

show abstract

mentioning

confidence: 99%

“…Structurally related 5-hydroxy-6-methyluracil (HMU, 2 ) is a known drug with immunotropic activity, and there is evidence in the literature for its potential antioxidant activity . Indeed its rate constant for reaction with ethylbenzene peroxyl radicals was reported as k = 2.6 × 10 4 M −1 s −1 . A recent investigation has shown that during the thermal decomposition of 2,2′-azo-isobutyronitrile (AIBN) in 2-propanol at 75 °C (in air) HMU prevented the radical-mediated oxidation of the solvent (to form acetone) as efficiently as the well-known antioxidant quercetin, by reacting with initiator-derived peroxyl radicals to yield product 4 .…”

mentioning

confidence: 99%

“…5 Indeed its rate constant for reaction with ethylbenzene peroxyl radicals was reported as k ) 2.6 × 10 4 M -1 s -1 . 5 A recent investigation has shown that during the thermal decomposition of 2,2′-azo-isobutyronitrile (AIBN) in 2-propanol at 75 °C (in air) HMU prevented the radical-mediated oxidation of the solvent (to form acetone) as efficiently as the well-known antioxidant quercetin, by reacting with initiator-derived peroxyl radicals to yield product 4. 6 However, the mechanism for such peroxyl-radical-quenching is far from being understood.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

et al. 2010

View full text Add to dashboard Cite

Addition of millimolar amounts of a weak base (pyridines) dramatically accelerates the reaction with peroxyl radicals of two biologically relevant uracil derivatives, 5-hydroxyuracil (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the formation of small amounts of the deprotonated form (pK(a) = 8.1-8.5 in water), which reacts with peroxyl radicals much faster than the parent undissociated form, via formal H-atom transfer from the OH in the 5 position.

show abstract

Antidotal and antiradical activity of complexes of β-glycyrrhizic acid with pyrimidine derivatives

Cited by 9 publications

References 0 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

Aminouracil and aminothiouracil as versatile precursors for a variety of heterocyclic systems

Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

Contact Info

Product

Resources

About