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1-(1',3',4',6'-tetra-O-acetyl-D-glucose)-4-para-substituted aromatic-[1,2,3]-triazole, preparation method and application thereof

A technology of acetyl and glucose, applied in 1-(1',3',4',6'-tetra-O-acetyl-D-glucose)-4-para-substituted aryl-[1,2 ,3]-triazole and its preparation method and application field, can solve the problems of reducing the quality of life of patients, bone marrow suppression, gastrointestinal dysfunction, etc.

Active Publication Date: 2015-09-30
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy and radiotherapy can kill normal cells as well as cancer cells, and can also cause side effects such as gastrointestinal dysfunction and bone marrow suppression, greatly reducing the quality of life of patients

Method used

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  • 1-(1',3',4',6'-tetra-O-acetyl-D-glucose)-4-para-substituted aromatic-[1,2,3]-triazole, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate, methanol as solvent, azide reagent as trifluoromethanesulfonyl azide.

[0026] Weigh compound 1 (4.313 g, 20 mmol) dissolved in K 2 CO 3 (7.452 g, 54 mmol) and CuSO 4 .5H 2 O (50 mg, 0.2 mmol) in methanol (84 mL) was filled with nitrogen for protection, and then stirred continuously for 30 min in an ice-water bath. Add compound with constant stirring 2 (5.030 g, 24 mmol), the ice-water bath was removed after the reaction was continued for half an hour, and the system was allowed to react at room temperature for 120 minutes.

[0027] TLC detection reaction. The solvent was evaporated under reduced pressure. The residue was azeotroped with 50 mL of toluene to remove water. After adding pyridine (100 mL, 20 mmol) to the above residue, Ac 2 O (15 mL, 160 mmol), stirred overnight. The solvent was distilled off under reduced pressure, and 50 mL of water was added to the residue. Extract wit...

Embodiment 2

[0028] Embodiment two: the synthesis of 4-p-methylbenzyl propargyl ether, THF is used as solvent

[0029] Weigh propargyl alcohol (155 mg, 2.774 mmol) and dissolve it in dry tetrahydrofuran (2 mL). Then use nitrogen protection, ice water external bath, and stir for 30 minutes. Weigh NaH (133 mg, 3.329 mmol), add to the solution, and react for 30 minutes. Then 4-p-methylbenzyl bromide (612.5 mg, 3.328 mmol) was added. After continuing the reaction for 3 hours, 1 mL of water was added to quench the reaction in an ice bath. Extract with 100 mL of dichloromethane three times. Using TLC detection, the developer (PE: EA=10: 1) confirmed that the reaction was complete. Use silica gel column for purification, eluent (PE:EA=20:1). Product carries out decompression distillation to remove solvent, finally obtains product 7a (355.3 mg, yield 80%).

Embodiment 3

[0030] Example 3: Synthesis of 4-p-methoxybenzyl propargyl ether, N, N'-dimethylformamide as solvent

[0031] Weigh propargyl alcohol (155 mg, 2.774 mmol) and dissolve it in dry N, N'-dimethylformamide (2 mL). Then use nitrogen protection, ice water external bath, and stir for 30 minutes. Weigh NaH (133 mg, 3.329 mmol), add to the solution, and react for 30 minutes. Then 4-p-methoxybenzyl bromide (665.5 mg, 3.328 mmol) was added. After continuing the reaction for 3 hours, 1 mL of water was added to quench the reaction in an ice bath. Extract with 50mL ether, three times. Using TLC detection, the developer (PE: EA=10: 1) confirmed that the reaction was complete. Use silica gel column for purification, eluent (PE:EA=20:1). Product carries out decompression distillation to remove solvent, finally obtains product 7b (355.3 mg, yield 80%).

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Abstract

The invention relates to preparation and application of 1-(1',3',4',6'-tetra-O-acetyl-alpha / beta-D-glucopyanosyl)-4-para-substituted benzyl oxyl methyl-[1,2,3]-triazole serial compounds, wherein the core structure thereof is formed by the substitution of 1,2,3-triazole derivatives at 1,4. The compounds have a good inhibitory activity for rectal carcinoma cells, and can serve as medicine for resisting rectal cancer. The synthetic method of the compounds comprises the following steps: a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate is prepared; 4-para-substituted arylpropargyl ether is prepared; 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and 4-para-substituted arylpropargyl ether are subjected to a click reaction in a solvent under the catalyzation of copper(i) to form 1-(1',3',4',6'-tetra-O-acetyl-alpha / beta-D-glucopyanosyl)-4-para-substituted benzyl oxyl methyl-[1,2,3]-triazole serial compounds.

Description

technical field [0001] The present invention relates to a compound 1-(1',3',4',6'-tetra-O-acetyl-α / β-D-glucopyranose)-4-para-substituted aryl with antitumor activity -[1, 2, 3]-triazole I and its preparation method and application. [0002] The present invention provides a compound 1-(1',3',4',6'-tetra-O-acetyl-α / β-D-glucopyranose)-4-para-substituted with good anti-rectal cancer activity Aryl-[1,2,3]-triazoles I. [0003] Background technique [0004] Rectal cancer refers to cancer between the dentate line and the rectosigmoid junction, and is one of the most common malignant tumors of the digestive tract. Rectal cancer is low in location and is easily diagnosed by digital rectal examination and sigmoidoscopy. At present, the treatment of rectal cancer needs to be based on surgery, supplemented by comprehensive treatment of chemotherapy and radiotherapy. For surgical treatment, because of its location deep into the pelvic cavity, the anatomical relationship is compli...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H1/00A61P35/00
CPCC07H1/00C07H19/056
Inventor 付伯桥覃彩芹吕珑杨新河
Owner HUBEI ENG UNIV
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