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Amino sugar derivative, preparation method thereof and medicinal application thereof

A drug and pharmaceutical technology, applied in sugar derivatives, sugar derivatives, pharmaceutical formulations, etc., can solve the problems of inability to completely eliminate tumor cells, high patient treatment costs, and long drug cycles.

Inactive Publication Date: 2009-12-02
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Because TAI achieves the purpose of inhibiting tumor growth by inhibiting the proliferation of endothelial cells, but cannot completely eliminate tumor cells, so the general drug cycle is longer
At present, most of the TAIs in clinical research and application are active proteins or molecules with complex structures, the preparation of drugs is relatively difficult, and the treatment cost of patients is high.

Method used

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  • Amino sugar derivative, preparation method thereof and medicinal application thereof
  • Amino sugar derivative, preparation method thereof and medicinal application thereof
  • Amino sugar derivative, preparation method thereof and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Preparation of N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranosyl)-3-phenyl-acrylamide hemihydrate (I-1)

[0118] 1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose (II-1)

[0119] Add ZnCl to the three-neck flask 2 (2.0g) and anhydrous acetic anhydride (54.0g, 50.0mL, 0.52mol), after heating for 30min, zinc chloride was dissolved, and D-glucose powder (10.0g, 0.056mol) was added in batches, and stirred thoroughly. After adding, continue heating on the oil bath (100°C) for about 2h. After cooling, the mixture was poured into 200 mL of ice water and stirred well to decompose unreacted acetic anhydride. An oily substance started to form, and then solidified into a large amount of white precipitate. Stirring was continued for 1 h, filtered, washed with cold water repeatedly, and then dried under an infrared lamp to obtain 18.11 g of a white solid (crude yield 83.58%). The solid was recrystallized from absolute ethanol (70 mL) to obtain a white solid, which was dried under an ...

Embodiment 2

[0140] N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranosyl)-3-(3,4-diacetoxyphenyl)-acrylamide semi Preparation of Hydrate (I-5)

[0141] Add 1.5g (8.33mmol) of caffeic acid into a solution formed by dissolving 1.15g (28.75mmol) of NaOH in 11ml of water under cooling in an ice bath, and slowly add Ac 2 O 2.27ml (20.82mmol), the solution became cloudy after the dropwise addition, removed the ice bath and stirred at room temperature for 1.5h. Stop the reaction with 10% H 2 5O 4 Adjust the pH of the solution to about 2-3, continue to stir for 20 minutes, filter, wash the filter cake several times with water, and dry under an infrared lamp to obtain 2.01 g of off-white solid (fully acetylated caffeic acid), with a yield of 91.36%.

[0142] Suspend 0.34 g (1.3 mmol) of fully acetylated caffeic acid in 10 mL of dry CH 2 Cl 2 0.70g (0.47mL, 5.5mmol) of oxalyl chloride was slowly added dropwise, the solution became clear, then a drop of anhydrous DMF was added dropwise, a large ...

Embodiment 3

[0150] N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranosyl)-3-(3-methoxy-4-acetoxyphenyl)- Preparation of Acrylamide Monohydrate (I-6)

[0151] Add 1.5g (7.73mmol) of ferulic acid into the solution formed by dissolving 0.8g (20.6mmol) NaOH in 7.7ml of water under cooling in an ice bath, and slowly add Ac 2 O 0.91ml (9.66mmol), the solution became cloudy after the dropwise addition, removed the ice bath and stirred at room temperature for 1.5h. Stop the reaction with 10% H 2 SO 4 Adjust the pH of the solution to 2-3, continue to stir for 20 minutes, filter, wash the filter cake with water several times, and dry it under an infrared lamp to obtain 1.74 g of off-white solid (acetylated ferulic acid), with a yield of 95.35%.

[0152] Suspend 0.31 g (1.3 mmol) of acetylated ferulic acid in 10 mL of dry CH 2 Cl 2 0.70g (0.47mL, 5.5mmol) of oxalyl chloride was slowly added dropwise, the solution became clear, then a drop of anhydrous DMF was added dropwise, a large number of bu...

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Abstract

The invention relates to the field of pharmaceutical chemistry, in particular to an N-glycosylation-3-aryl acrylamide derivative (I), wherein, the definitions of G and Ar are disclosed in the specification. A pharmacological experiment proves that the compound has a restraining function to the propagation of vascular endothelial cells and can be applied to the clinical therapy of tumours or chronic inflammation.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of N-glycosyl-3-aryl acrylamide derivatives, their preparation method and their inhibitory effect on the proliferation of vascular endothelial cells. Background technique [0002] Tumor angiogenesis inhibitors (tumor angiogenesis inhibitor, TAI) can destroy or inhibit angiogenesis, effectively prevent tumor growth, metastasis and recurrence, and show great advantages compared with traditional anti-tumor drugs. Currently, tumor angiogenesis inhibitors in clinical trials can be divided into the following categories based on their mechanism of action: ① Growth factor inhibitors that stimulate angiogenesis: such as Bevacizumab; ② Receptor tyrosine kinases Inhibitors, such as imatinib; ③ Matrix metalloproteinase (MMPs) inhibitors, such as Neovastat, which is a natural MMP inhibitor extracted from shark cartilage; ④ Drugs that directly inhibit endothelial cell proliferation, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04A61K31/7024A61P35/00A61P29/00
Inventor 徐云根姚硕蔚尤启冬张飞皇董缙杨波靳娜何俏军翁勤洁
Owner CHINA PHARM UNIV
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