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Active dextran tetra saccharide alkyl glycoside and its prepn process and application

A technology of glutrans alkyl glycosides and compounds, which is applied in the field of glucan tetrasaccharide alkyl glycoside compounds, can solve the problems of increasing the difficulty of patient recovery, damaging the vitality of patients, killing tumor cells, etc., and achieving simple structure and high quality. The effect of controllability and simple preparation method

Inactive Publication Date: 2007-03-21
CHONGQING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ordinary chemotherapeutic drugs have no specificity. They kill tumor cells and a large number of normal cells at the same time. They have great toxic and side effects on the human body, and also damage the vitality of patients, making it more difficult for patients to fully recover.

Method used

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  • Active dextran tetra saccharide alkyl glycoside and its prepn process and application
  • Active dextran tetra saccharide alkyl glycoside and its prepn process and application
  • Active dextran tetra saccharide alkyl glycoside and its prepn process and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of tetrasaccharide II

[0023] 1. Preparation of monosaccharide receptor 3

[0024]

[0025] (1), preparation of monosaccharide donor 1

[0026] In the reactor, add D-glucose (3.60g, 20.0mmol), trityl chloride (6.69g, 24.0mmol) and 40ml of pyridine, heat to 70°C, stir for 8 hours, cool to 0°C, add benzene Formyl 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, spin dry, add 100ml of dichloromethane, 100ml of methanol, 0.2ml of acetyl chloride, stir at room temperature for 1 hour, neutralize with triethylamine, evaporate the solvent, add 40ml of pyridine, 30ml of acetic anhydride, and stir for 4 hours at room temperature. Spin to dry, add 90ml of tetrahydrofuran, 60ml of methanol, saturate with ammonia, and stir for 4 hours. Spin to dry, add 50ml of dichloromethane, K 2 CO 3 3g, 3ml of trichloroacetonitrile, reacted...

Embodiment 2

[0037] Preparation of tetrasaccharide III

[0038] 1. Preparation of monosaccharide receptor 7

[0039]

[0040] In the reactor, add 1 (1.29g, 1.9mmol), dodecanol (0.50g, 2.7mmol), dichloromethane 20ml, trimethylsilyl trifluoromethanesulfonate (TMSOTF) 30μl, and stir at room temperature to react 2 After hours, it was neutralized with triethylamine, concentrated and purified on a silica gel column, using petroleum ether / ethyl acetate (5 / 1) as eluent, and the corresponding components were collected to obtain 6 (1.11 g), with a yield of 83%.

[0041] In the reactor, add 6 (0.98g, 1.4mmol), 2ml of dichloromethane, 40ml of anhydrous methanol, and 0.2ml of acetyl chloride, leave it at room temperature for 5 hours, neutralize with triethylamine, distill off the solvent, and dissolve the sample in dichloromethane Purify on a silica gel column, use petroleum ether / ethyl acetate (3 / 1) as eluent, collect the corresponding components to obtain 7 (0.80g), yield 86%, [α] D -9.8° (c1.0,...

Embodiment 3

[0047] Preparation of tetrasaccharide IV

[0048] 1. Preparation of monosaccharide receptor 10

[0049]

[0050] In the reactor, add 1 (1.29g, 1.9mmol), cetyl alcohol (0.61g, 2.5mmol), dichloromethane 20ml, boron trifluoride-diethyl ether 0.5ml, stir at room temperature for 2 hours, and use triethylamine After neutralization and concentration, it was refined on a silica gel column, using petroleum ether / ethyl acetate (6 / 1) as eluent, and the corresponding components were collected to obtain 9 (1.20 g), with a yield of 83%.

[0051] In the reactor, add 9 (1.06g, 1.4mmol), 2ml of dichloromethane, 40ml of anhydrous methanol, and 0.2ml of acetyl chloride, leave it at room temperature for 5 hours, neutralize with triethylamine, distill off the solvent, and dissolve the sample in dichloromethane Purify on a silica gel column, use petroleum ether / ethyl acetate (4 / 1) as eluent, collect the corresponding components to obtain 10 (0.90g), yield 90%, [α] D .-2.0° (c1.0, CHCl 3 ); 1...

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Abstract

The present invention relates to active dextran tetrasaccharide alkyl glycoside compound with the structure as shown in the generation expression. The present invention also relates to the preparation process and application in preparing antitumor medicine of the compound.

Description

technical field [0001] The invention relates to a non-natural and artificially synthesized glucan tetrasaccharide alkyl glycoside compound, its preparation method and the application of the compound in the preparation of antitumor drugs. 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-macrophage system, lymphocyte system, and granulocyte system. When the body has normal physiological functi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04C07H3/06A61K31/7028A61K31/702A61P35/00
Inventor 衡林森
Owner CHONGQING UNIV OF POSTS & TELECOMM
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