Visokomerniye tritium derivatives of sialic acid
(57) Abstract:Describes visokomerniye tritium derivatives of sialic acid of General formula I
< / BR>where R is CH3or
< / BR>The technical result is the expansion of the range labeled analogs of the physiologically active compounds. The invention relates to the field of organic chemistry and can find application in biology and medicine.In the study of physiologically active compounds need to be labeled analogs.Known derivatives of sialic acid of General formula I:
< / BR>where R is CH3or
< / BR>-methylglucoside N-acetyl-neuraminic acid and disagreggated N-acetyl-neuraminic acid, respectively.These compounds are functional fragments of gangliosides and glycoproteins and used for the study of higher nervous activity. In addition, they are components of all types of mucoproteins, mucopolysaccharides and some mucolipidosis. Erythrocytes of animals contain sialic acid in the form of N-glycolylated groups (R. Schauer. Sialic Acids: Chemistry, Metabolism, And Function. Ed. Springer-Verlag, New York, 1983, 346 pp).However, tritium-labeled analogues of data Izvestia getting wisokomernix tritium compounds of General formula I.Below are examples of implementation of the invention.Example 1. The reaction vial was placed 2 mg-methylglucoside N-acetyl-neuraminic acid, put on 50 mg of 5% Pd/caso3then the ampoule was evacuated to a pressure of 0.1 PA, filled with gaseous tritium to pressure 333 hPa and kept at a temperature of 200oWith 5 minutes of Excess tritium was removed by vacuum. After cooling the reaction products were dissolved in water (6x1 ml), the catalyst was filtered, and the filtrate was evaporated several times to remove the labile tritium. The residue was chromatographically first by TLC on silicagel records in the system methanol-acetonitrile-water (3:3:2). The zone containing the desired substance, cut and labeled drug was suirable with a mixture of water with methanol (9:1) (5x1 ml). Eluate was evaporated, dissolved in 1 ml of a mixture of methanol-water (9:1) and filtered. Final purification was performed by HPLC. The output labeled drug 20-25%, and the molar radioactivity of 12.5 CI/mmol.Analysis and purification of labeled preparation was carried out thin-layer (TLC) and high performance liquid (HPLC) chromatography.Sodium salt of methylglucoside N-acetyl-neuraminic acid:
TLC (Sorbfil) - isopropanol-atlacatl acetonitrile-water-triperoxonane acid (70:30:0.05) retention time 13,00 min; in the system acetonitrile-water-triperoxonane acid (70:30:0.1) retention time of 6.96 min-Disagreggated N-acetyl-neuraminic acid:
TCX(Sorbfil) -isopropanol-ethyl acetate-water (4:3:2), Rf of 0.15; methanol-acetonitrile-water (3:3:2), Rf of 0.65;
HPLC - Separon NH2, 7 μm, 3150 mm, v - 0.5 ml/min, acetonitrile-water-triperoxonane acid (80:20:0,08) retention time 5,32 minutesFor receiving and processing the chromatographic data were used hardware-software complex "Multichrom 1.5" (LLC "ampersand character", Russia) based on IBM PC/AT. Radioactivity was measured by scintillation counter with an efficiency of registration of tritium 30% in dioxane scintillator.Example 2. The reaction vial was placed 4 mg-disagreggated N-acetyl-neuraminic acid, printed on 100 mg of 5% Pd/caso3then it was evacuated to a pressure of 0.1 PA, filled with gaseous tritium to pressure 333 hPa and kept at a temperature of 160oWith 20 minutes of Excess tritium was removed by vacuum. After cooling the reaction products were dissolved in water (61 ml), the catalyst was filtered, and the filtrate was evaporated several times to remove the labile tritium. The residue was chromatographically first by TLC on silicagel the drug was suirable with a mixture of water with methanol (9:1) (51 ml). Eluate was evaporated, dissolved in 1 ml of a mixture of methanol-water (9:1) and filtered. Final purification was performed by HPLC. The output labeled drug 10-15%, and the molar radioactivity 8,0-9,0 CI/mmol.Thus, the resulting new visokomerniye tritium derivatives of sialic acid-methylglucoside N-acetyl-neuraminic acid and disagreggated N-acetyl-neuraminic acid. Visokomerniye tritium derivatives of sialic acid of General formula I
< / BR>where R= CH3or
R-NH-CO-NH-NH2(I) where R = D-glucosyl-D-galactosyl-L-arabinosyl-that can be used for the synthesis of compounds possessing anti-inflammatory, antimicrobial activity
FIELD: organic chemistry, chemical technology, medicine.
SUBSTANCE: invention relates to a method for preparing 1-isonicotinyl-2-D-glucosyl hydrazone. In the glucosylation reaction of isonicotinic acid hydrazide the method involves using anionite AN 31 GS as a catalyst of the enhanced effectiveness, and using 95-96.5% ethanol or 85-90% isopropanol as the reaction medium. At the final stage the method involves sorption of contaminating impurities with activated carbon followed by drying the end product in nitrogen atmosphere.
EFFECT: improved preparing method.
2 cl, 1 ex
FIELD: organic chemistry, medicine, pharmacy.
SUBSTANCE: invention relates to geranyl compounds represented by the following formulas (I-1) , (I-2) or (I-3) wherein R1 means compounds of the following formulas: or R2 means a group remaining after removing all carboxyl groups presenting in carboxylic acid chosen from group consisting of malic acid, citric acid, succinic acid, fumaric acid and others; m = 1, 2 or 3; n = 0, 1 or 2, and m + n represent a number of carboxylic groups presenting in indicated carboxylic acid; R3 means p-hydroxyphenyl or mercapto-group. Also, invention relates to derivatives of mevalonic acid represented by the following formula (I-4): wherein R means -CH2OH or CH3. Also, invention to an antitumor agent comprising as an active component geranyl compound of formulas (I-1), (I-2) or (I-3) or derivative of mevalonic acid of the formula (I-4), and optionally a pharmaceutically acceptable carrier or solvent. Also, invention relates to a method for treatment of liver cancer based on using geranyl compound of formulas (I-1), (I-2) or (I-3), or derivative of mevalonic acid of the formula (I-4) and using proposed compounds in manufacturing an antitumor agent. Invention provides using geranyl compounds or derivatives of mevalonic acid as antitumor agents.
EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.
7 cl, 3 tbl, 17 ex
SUBSTANCE: method involves preliminary acetylation of chitin with acetic anhydride, washing and drying the acetylated chitin in order to reduce degree of deacetylation thereof and, as a result, increase output of the desired product - D(+)-glucosamine hydrochloride when obtaining said product through hydrolysis of acetylated chitin with concentrated hydrochloric acid while heating, followed by evaporation, crystallisation, separation, washing and drying the desired product.
EFFECT: high output of the desired product while maintaining its high quality; method is more environmentally friendly since pre-treatment of chitin reduces the amount of processing wastes.
1 cl, 2 ex
SUBSTANCE: invention relates to use of 2-mercaptobenzoyl hydrazones of monose of formula (where the name of monose and value of radicals are listed in the table) as antimocrobial and antifungal agents.
EFFECT: use of 2-mercaptobenzoyl hydrazones of monose of formula (I) as antimicrobial and antifungal agents.
2 tbl, 2 ex
FIELD: medicine, pharmaceutics.
SUBSTANCE: present invention refers to a new method for the chemical synthesis of asymmetrically or symmetrically substituted β-(1→6)-bound glucosamine disaccharide of formula (1), as well as to a method for purifying it. The invention declared the intermediate compounds referred to the given method.
EFFECT: invention refers to a pharmaceutical composition comprising the mentioned compounds, and to the use of the compounds in treating the disorders affected by immune system activity modulation, including the inhibition or activation of the immune system, such as a disorder selected from immune disorders and/or cancer.
26 cl, 8 ex, 26 dwg
FIELD: medicine, pharmaceutics.
SUBSTANCE: present invention refers to new compounds of general formula I [X]n-Y-ZR1R2, wherein the radicals are specified in the description, effective as heparan sulphate-binding protein inhibitors. The invention also refers to a pharmaceutical or veterinary composition having heparan sulphate-binding protein inhibitory activity for preventing or treating a disorder in a mammal, and to the use of these compounds and compositions for antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic therapy in a mammal.
EFFECT: preparing the new compounds of general formula I [X]n-Y-ZR1R2, wherein the radicals are specified in the description, effective as the heparan sulphate binding protein inhibitors.
10 cl, 31 ex, 11 tbl, 40 dwg
FIELD: organic chemistry, chemical technology.
SUBSTANCE: invention relates to a continuous method for synthesis of sulfamate derivatives of fructopyranose of the general formula (I): wherein R1, R2, R3, R4, R5, R6 and X have values given in the invention description. Invention relates to synthesis of thiopyramate with using glyme as organic solvent in both steps of the continuous process of synthesis.
EFFECT: improved method of synthesis.
17 cl, 8 tbl, 6 ex
SUBSTANCE: invention relates to the new hem-difluoridated compound of the formula: where R1 represents a group, containing alkyl chain or amino group; R2 represents hydrogen atom, either free or protected functional group of alcohol; R3 represents a group CH2OH, CH2-OGP, where GP respresents protecting group such as alkyl, benzyl (Vp), trimethylsilyl (TMS), tert-butyldimethylsilyl (TBDMS), tert-butyldiphenylsilyl (TBDPS), acetate (Ac); Y, Y', Y" represent independent groups OR, where R represents H, benzyl, Ac, TMS, TBDMS, TBDPS that are used for producing antitumor, antiviral, hypoglycemic and anti-flammatory medicine and compounds for immunology and cosmetology, or glyco peptide analogs of antifreeze molecules. The invention refers particularly also to the new hem-difluoridated compound of the general formula: and to the method of producing new hem-difluoridated compound of the formula: .
EFFECT: compounds possess increased effectiveness.
7 cl, 8 ex, 24 dwg
SUBSTANCE: method to produce maltobionat provides for production of a substrate applied in process of production of mash or mesh and containing maltose; and conversion of maltose into maltobionat by means of a reaction catalysed with carbohydratoxidase, for instance, carbohydratoxidase from Microdochium nivale CBS 100236. At the same time maltobionat is formed at the stage of mashing in process of beer production.
EFFECT: invention provides for practically full conversion of maltose in a substrate into a maltobionat.
6 cl, 1 tbl, 3 ex