Glycyrrhizic acid and its 30-methyl ester were conjugated with 2-amino-1,3,4,6-tetra- O -acetyl-2-deoxy-α- D -glucopyranose, 2,3,4,6-tetra- O -acetyl-β- D -glucopyranosyl amine, 2,3,4-tri- O -acetyl-α- L -arabinopyranosyl amine, 2-acetamido-2-deoxy-β- D -glucopyranosyl amine, and β- D -galactopyranosyl amine using N , N ′-dicyclohexylcarbodiimide and its mixtures with N -hydroxybenzotriazole. Structures of the conjugates were confirmed by IR, UV, 1 H, and 13 C NMR spectroscopy. The glycoconjugate with the residues of 2-acetamido-2-deoxy-β- D -glucopyranosyl amine in the carbohydrate part of its molecule exhibited antiviral activity (ID 50 4 μg/ml) toward the herpes simplex type 1 virus (HSV-1) in the VERO cell culture. Two compounds demonstrated anti-HIV-1 activity (50–70% inhibition of p24) in a culture of MT-4 cells at concentrations of 0.5–20 μg/ml.
New cysteine-containing derivatives of glycyrrhizic acid were synthesized by its coupling with Cys(Bzl) esters or the Cys(Bzl)-Val-OBu t dipeptide by the active ester method (DCC/HOSu) or by Woodward's reagent K. The derivatives with Cys(Bzl) and Cys(Bzl)-Val residues attached to the carbohydrate part of the molecule stimulated the primary immune response and the reaction of delayed-Type hypersensitivity in mice at a dose of 2 mg/kg.
New amino acid derivatives of glycyrrhizic acid and its methyl ester were selectively synthesized using active N -succinimide esters. The compounds with residues of glycine ethyl ester and alanine methyl and butyl esters increased the level of agglutinins and hemolysins in blood serum of mice two- to threefold in comparison with the control upon parenteral administration at a dose of 2 mg/kg for 14 days.
Starting from (+)-Δ3-carene, synthetic equivalents of the C10-C16 fragment of epothilone carbo- analogs were obtained.
Triterpene saponins, glycoside analogues of glycyrrhizic acid with a modified carbohydrate chain containing monosaccharide residues attached through ester bonds, were synthesized. To this end, peracetylated glycyrrhizic acid or its 30-methyl ester were glycosylated by 2,3,4,6-tetra- O -acetyl-α- D -gluco- or -α- D -galactopyranosyl bromide in dichloroethane in the presence of Ag 2 CO 3 . Glycerrhetinic acid saponin with D -Gal p residues exhibited a higher antiulcer activity than glycyrrhizic acid in rats at a dose of 25 mg/kg.
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Starting from (+)-Δ 3 -carene, synthetic equivalents of the C 10 -C 16 fragment of epothilone carbo- analogs were obtained.
A bidentate organic compound containing nitrogen and sulfur donor atoms was tested as a reagent for extraction of iridium(IV) from aqueous solutions. The composition of the extractable Ir(IV) complex was determined by 1H NMR, UV, and IR spectroscopy and elemental analysis.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Extraction of ruthenium(III) from hydrochloric solutions with a polyfunctional S,N-containing extractant was studied. The mechanism of metal ion extraction was found to depend on the time of phase contact. A composition for the extractable compound was proposed on the basis of electronic, H-1 NMR, and IR spectroscopy and elemental analysis.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
The compositions of iridium(III) chloro complexes with dimethyl sulfoxide and its alkylthio derivative were determined based on the data of electronic, IR, and H-1 NMR spectroscopy. Configurations for the complexes were proposed.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
A series of new N-substituted cytisine derivatives was synthesized. The 1 H and 13 C NMR spectra of certain compounds exhibit a doubled set of signals. This is explained by formation of diastereomeric pairs in compounds containing an asymmetric center in the substituents. The signal splitting in -COHC=CHCO 2 H and HC=O (formyl) derivatives is explained by the existence of Z and E invertomers. Their stereochemical features are discussed. Amide conjugation is confirmed by temperature experiments.
Some geminal dimethyl-substituted functionalized C4-synthons were prepared on the basis of (±)-pantolactone.
Benzyl esters of glycyrrhizic acid were synthesized using PhCH 2 Br in DMSO-CH 2 Cl 2 -NaOH in the presence of phase-transfer catalysts, such as tetraalkylammonium salts and 2-methyl-2-propanol.
The reactions of methylmanganese iodide with levoglucosenone, its dihydro derivative, and 1.6-anhydro-3-deoxy-4-O-methyl-β-d-erythro-hexopyran-2-ulose were found to be highly diastereoselective compared to the reactions of Li-, Mg-, and Cu-based reagents. This specific feature of the manganese reagent is due to the enhanced tendency of manganese for chelation.