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Preparation method of dextran (IV) alkyl glycosides compounds

A technology of glutrans alkyl glycosides and compounds, which is applied in the field of preparation of glucan tetrasaccharide alkyl glycosides, can solve problems such as low yield and long synthesis route, achieve reduction of synthesis reaction steps and great practical value , easy to store for a long time

Inactive Publication Date: 2009-03-11
CHONGQING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Accordingly, in order to study the relationship between the structure of oligosaccharides and anticancer activity, we once designed and synthesized dodecyl heptaglucoside (see Heng Linsen, Li Zhimin. A class of unnatural active oligosaccharide compounds and their preparation methods and Application [P]. Chinese patent ZL 200510020578.4.2005-10-26.), and then designed and synthesized dodecyl β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl Pyranosyl-(1→6)]-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (see Lu Haibin, Jiang Xiaohui, Heng Linsen. Dodecyl β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl-(1→6)- Synthesis of β-D-glucopyranoside. Chemical Research and Application, 2007, 19 (6): 637-640), animal test results showed that the compound had a better tumor inhibitory effect on S180-bearing mice than dodecyl heptaglucoside It has a better tumor inhibitory effect on S180-bearing mice; but the synthetic route reported in the literature is longer and the yield is lower

Method used

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  • Preparation method of dextran (IV) alkyl glycosides compounds
  • Preparation method of dextran (IV) alkyl glycosides compounds
  • Preparation method of dextran (IV) alkyl glycosides compounds

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Experimental program
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Effect test

Embodiment 1

[0014] 1. Preparation of monosaccharide receptor 6

[0015]

[0016] (1), preparation of monosaccharide 5

[0017] In the reactor, add D-glucose 1 (3.60g, 20.0mmol), trityl chloride (6.69g, 24.0mmol) and 40ml of pyridine, heat to 70°C, stir for 8 hours to generate 2, cool to 0 ℃, added benzoyl chloride (10.3mL, 88mmol), stirred at room temperature for 24 hours, added 100ml of dichloromethane, followed by water, 1N HCl, saturated NaHCO 3 / H 2 O wash, anhydrous Na 2 SO 4 Dry and spin dry to obtain 3, dissolve 3 with 40 milliliters of dichloromethane, add 20 milliliters of acetic anhydride, 20 milliliters of glacial acetic acid and 10 milliliters of concentrated sulfuric acid to this solution, react at room temperature for 2 hours, add 150 milliliters of dichloromethane methane, then add 200 milliliters of water under stirring, discard the water phase after standing for stratification, then use saturated sodium bicarbonate solution to wash away the acid in the organic phas...

Embodiment 2

[0033] Animal tumor inhibition test

[0034] Take 60 Kunming mice, weighing 18-22g, both male and female. Take ascites tumors 7-8 days after inoculation and count them according to 1:15 dilution, so that the final concentration is 10 million S180 tumor cells / ml; each mouse is inoculated with 0.2ml in the armpit. (Containing 2 million S180 tumor cells), the next day were randomly divided into 5 groups: synthetic compound 94mg / kg, 2mg / kg, 1mg / kg, blank control group and cyclophosphamide (CY) 40mg / kg group, drug group Administration once a day (tail vein injection iv), continuous administration for 10 days, the control group was given the corresponding volume of normal saline (NS) solution, CY group was administered once a day, the drug was stopped for one day after the last administration, and the neck was dislodged. Animals were weighed, tumors were dissected and weighed, the tumor inhibition rate was calculated according to the formula, and the differences among groups were c...

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Abstract

The invention provides a convenient and practical method for preparing dodecyl Beta-D- glucopyranosyl-(1to3)-Beta-D- glucopyranosyl-(1to6)]-Beta-D- glucopyranosyl-(1to6)-Beta-D-glucopyranoside, which shortens the steps of synthesis reaction, improves the yield and has great practical value.

Description

technical field [0001] The present invention relates to the preparation method of a kind of dextran tetraose alkyl glycoside compound which has biological activity and can be used for medicine, specifically dodecyl β-D-glucopyranosyl-(1→3 A preparation method of )-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl. Background technique [0002] According to current knowledge, most of the sugars that can enhance animal immunity and have anti-tumor activity are polysaccharides, such as polysaccharides extracted from practical fungi such as lentinan, ganoderma lucidum polysaccharide, and schizophyllan, or polysaccharides extracted from Chinese herbal medicines. There are not many oligosaccharides that have been clearly studied and have clear immune and anti-tumor activities. Studies have shown that the tumor-suppressing effect of sugar is achieved through the body's immune system. The types of immune active cells in the body mainly include monocyte-macropha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04
CPCY02P20/55
Inventor 衡林森赵晓玲沈燕贾云灿岳学荣刘小琴刘坤段江红
Owner CHONGQING UNIV OF POSTS & TELECOMM