4-(glucopyranosyl) semicarbazides as intermediate products for the synthesis of compounds with anti-inflammatory and antimicrobial activity

 

(57) Abstract:

The use of the invention as intermediates for the synthesis of compounds with anti-inflammatory and antimicrobial activity. The essence of the invention: 4-(glucopyranosyl)semicarbazides of the formula RNHCONHNH2when R;,%; so pl., °C; []2D0a) D-galactosyl; 70; 168 - 170; +10,4 (c 1, water); b) D-glucosyl; 55; 148 - 150; -14,6 (c 1, water); C) L-arabinopyranosyl; 43,5; 134 - 135; +44,1. Reagent 1: N-methyl - N-glyukopiranozil-N-nitrosoanatabine formula RNHCON(NO)CH3Reagent 2: hydrazinehydrate. Reaction conditions: at 25 To 60°C and stirring.

The invention relates to new compounds of the number of semicarbazides, namely 4-(glucopyranosyl) semicarbazides General formula

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.

The aim of the invention is the expansion of raw materials for the synthesis of substances with biological activity, in particular anti-inflammatory, antimicrobial activity.

This goal is achieved by the proposed 4-(glucopyranosyl) semicarbazides total f

R NH --CH3where R = D-glucosyl-D-galactosyl-L-arabinosyl, with hydrazine hydrate.

The compound of General formula I can be used for the synthesis of 4-(glucopyranosyl) semicarbazones 5-nitrofurfural possessing anti-inflammatory, antimicrobial activity.

P R I m e R 1. Getting 4-(-D-galactopyranosyl) semicarbazide.

To a chilled solution of 2.7 g (0.01 mol) of galactopyranosides in 20 ml of methanol with stirring, poured dropwise 1 ml (0.015 mol) of hydrazine hydrate. The resulting mixture is heated to 25aboutC and incubated for 1 h Precipitated white precipitate is filtered off, washed with methanol, dried over CaCl2.

Yield 70% ; so pl. 168-170aboutC; []D20= + 10,4 (C 1, water). Rf0,54 (ethanol-chloroform-acetone 2:1:1).

Found, %: C 34,15; H Of 6.65; N 16,9.

Calculated, %: C 35,44; H 6,33; N 17,7.

The IR spectrum of 4-(-D-galactopyranosyl) semicarbazide most are characteristic absorption bands:

(KBr - table), maxcm-11695 (C = O), 1620 (H-O-H), 1595 (NH), 1410 (C-N), 1185, 1120, 1085, 1045, 1020, 920 (C-O-C carbohydrate rings).

Based on these data can be represented by structural formula

< / BR>
The connection corresponds policebased.

To a chilled solution of 2.7 g (0.01 mol) of glucoronosyltransferase 15 ml (0.015 mol) of hydrazine hydrate. The resulting mixture is heated to 25aboutAnd stirring was incubated for 1 h the Precipitate is filtered off, washed with methanol. Air-dried.

Yield 55% ; so pl. 148-150aboutC; []D20= - 14,6 (C 1, water). Rf0,61 (ethanol-chloroform-acetone 2:1:1).

Found, %: C 35,2; H 6,2; N 17,8.

Calculated, %: C 35,44; H 6,33; N 17,7.

The IR spectrum of 4-(-D-glyukopiranozil) semicarbazide most are characteristic absorption bands:

(KBr - table), maxcm-1: 1745 (C = O), 1585 (N-H), 1320 (C-N), 1120, 1090, 1050, 980, 900 (C-O-C carbohydrate rings).

Based on these data can be represented by structural formula

< / BR>
The connection corresponds to the molecular formula C7H15N3O6.

P R I m e R 3. Getting 4-(-L-arabinopyranosyl)semicarbazide.

To the cooled solution 4,72 g (0.02 mol) of 1-methyl-1-nitroso-3(-L-arabinopyranosyl) urea in 15 ml of methanol with stirring, poured dropwise 2 ml (0.03 mol) of hydrazine hydrate. The mixture was kept at 60aboutC in a water bath. The solution is cooled, the precipitate filtered off, washed with methanol. Colorform-acetone 2:1:1).

Elemental analysis. Found, %: C To 34.5; H 6,1; N 20, 47.

Calculated, %: C 34,78; H 6,28; N 20,61.

The IR spectrum of 4-(-L-arabinopyranosyl) semicarbazide are characteristic absorption bands:

(KBr - PL.),maxcm-1: 1650 (C = O), 1540 (N-H), 1400 (OH), 1150, 1080, 990, 930 (C-O-C carbohydrate rings).

Based on these data can be represented by structural formula

< / BR>
The connection corresponds to the molecular formula C6H13N3O6.

An advantage of the claimed invention is that the proposed connections allow easy affordable way to obtain carbohydrate analogues furatsilina, which have anti-inflammatory, antimicrobial activity and can be used in medicine.

4-(GLUCOPYRANOSYL) SEMICARBAZIDES AS INTERMEDIATE PRODUCTS FOR THE SYNTHESIS OF COMPOUNDS WITH ANTI-INFLAMMATORY AND ANTIMICROBIAL ACTIVITY.

4-(Glucopyranosyl)semicarbazides General formula

R - NH - CO - NHNH2,

where R - D-glucosyl, D-galactosyl - or L-arabinosyl-,

as intermediate products for the synthesis of compounds with anti-inflammatory and antimicrobial activity.

 

Same patents:

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

FIELD: chemistry.

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

FIELD: chemistry.

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

Up!