2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose and preparation method and application thereof

An acetyl, glucose technology, applied in 2-(1',2',3'-triazole-4'-oxybenzyl)-1,3,4,6-O-acetyl-D- Glucose and its preparation and application fields can solve the problems of reducing the quality of life of patients, bone marrow suppression, gastrointestinal dysfunction, etc.

Active Publication Date: 2015-08-05
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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  • 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose and preparation method and application thereof
  • 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose and preparation method and application thereof
  • 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose and 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, and imidazole-1-sulfonyl azide as the azide reagent.

[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...

Embodiment 2

[0028] Example 2: Synthesis of 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate, methanol as solvent, azide reagent as trifluoromethanesulfonyl azide.

[0029] 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 (4.20 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 2 hours.

[0030] 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 with eth...

Embodiment 3

[0031] Embodiment three: the synthesis of phenyl propargyl ether, DMF is used as solvent.

[0032] Benzyl alcohol (300 mg, 2.774 mmol) was weighed and dissolved in dry DMF (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 3-bromopropyne (413 mg, 3.472 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=10:1). The product was distilled under reduced pressure to remove the solvent, and finally the product 6 (326 mg, yield 64.3%) was obtained.

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Abstract

The core structure of 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose with an anti-colorectal carcinoma activity is that a 1,2,4-triazole derivative substitutes 2-site of 1,3,4,6-O- acetyl-D-glucose. The above compound has a good activity of inhibiting colorectal carcinoma cells, and can be used as an anti-colorectal carcinoma medicine. A synthesis method of the above compound comprises the following steps: 2-amino-D-glucose hydrochloride and an azidation reagent are used as raw materials to generate a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate under an alkaline condition; 3-propargyl bromide and phenylcarbinol react under the action of sodium hydride to generate phenyl propargyl ether; and the 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and phenyl propargyl ether undergo a click reaction in a solvent under the catalysis of monovalent copper to generate 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose.

Description

technical field [0001] The present invention relates to compounds 2-(1',2',3'-triazole-4'-oxybenzyl)-1,3,4,6-O-acetyl-D-glucose and Its preparation method and application. [0002] The present invention provides a compound 2-(1',2',3'-triazole-4'-oxybenzyl)-1,3,4,6-O-acetyl-D- Glucose 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 complicated, the operation is not easy to complete, and the postoperative recurrence rate is high. The middle and lower rectal cancer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H1/00A61P35/00
CPCC07H1/00C07H19/056
Inventor 付伯桥覃彩芹吕珑李伟
Owner HUBEI ENG UNIV
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