1‑(1',3',4',6'–tetra‑o‑acetyl‑α/β‑D‑glucopyranose)‑4‑para-substituted aryl‑[1, 2, 3]‑ Triazole and its preparation method and application

A glucose, acetyl-based technique applied in 1-(1',3',4',6'-tetra-O-acetyl-α/β-D-glucopyranose)-4-para substitution Aryl-[1, 2, 3]-triazoles and their preparation and application fields can solve the problems of reducing the quality of life of patients, bone marrow suppression, and gastrointestinal dysfunction

Active Publication Date: 2018-03-23
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‑α/β‑D‑glucopyranose)‑4‑para-substituted aryl‑[1, 2, 3]‑ Triazole and its preparation method and application
  • 1‑(1',3',4',6'–tetra‑o‑acetyl‑α/β‑D‑glucopyranose)‑4‑para-substituted aryl‑[1, 2, 3]‑ Triazole and its preparation method and application
  • 1‑(1',3',4',6'–tetra‑o‑acetyl‑α/β‑D‑glucopyranose)‑4‑para-substituted aryl‑[1, 2, 3]‑ Triazole and its preparation method and application

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 trifluoromethanesulfonyl azide as the azide reagent.

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

[0027] TLC detects the reaction. The solvent was evaporated under reduced pressure. The residue was used to azeotropically remove water with 50 mL of toluene. After adding pyridine (100 mL, 20 mmol) to the above residue, slowly add Ac 2 O (15 mL, 160 mmol), stir overnight. The solvent was distilled off under reduced pressure, and 50 mL of water was a...

Embodiment 2

[0028] Example 2: Synthesis of 4-p-methylbenzyl propargyl ether with tetrahydrofuran 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 outer bath, and stir for 30 minutes. Weigh out NaH (133 mg, 3.329 mmol), add it to the solution, and react for 30 minutes. Then 4-p-methylbenzyl bromide (612.5 mg, 3.328 mmol) was added. Continue the reaction for 3 hours and then add 1 mL of water to quench under ice bath conditions. Extract with 100 mL of dichloromethane, and extract three times. Using TLC detection, developing reagent (PE: EA=10 :1) confirms that the reaction is complete. Use silica gel column for purification, eluent (PE:EA=20:1). The product was distilled under reduced pressure to remove the solvent, and finally product 7a (355.3 mg, yield 80%) was obtained.

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 outer bath, and stir for 30 minutes. Weigh out NaH (133 mg, 3.329 mmol), add it to the solution, and react for 30 minutes. Then 4-p-methoxybenzyl bromide (665.5 mg, 3.328 mmol) was added. Continue the reaction for 3 hours and then add 1 mL of water to quench under ice bath conditions. Extract with 50 mL of ether and extract three times. Using TLC detection, the developing agent (PE:EA=10:1) confirms that the reaction is complete. Use silica gel column for purification, eluent (PE:EA=20:1). The product was distilled under reduced pressure to remove the solvent, and finally product 7b (355.3 mg, yield 80%) was obtained.

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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 with anti-tumor activity 1-(1',3',4',6'-tetra-O-acetyl-α / β-D-glucopyranose)-4-para-substituted aryl group -[1, 2, 3]-Triazole I and its preparation method and application. [0002] The present invention provides a compound with good anti-rectal cancer activity 1-(1',3',4',6'-tetra-O-acetyl-α / β-D-glucopyranose)-4-para-substituted Aryl-[1, 2, 3]-triazole I. [0003] Background technique [0004] Rectal cancer refers to cancer from the dentate line to the junction of the rectum and sigmoid colon. It is one of the most common malignant tumors in the digestive tract. The location of rectal cancer is low, and it is easily diagnosed by digital rectal examination and sigmoidoscopy. At present, the treatment of rectal cancer requires surgery as the mainstay, supplemented by comprehensive treatment of chemotherapy and radiotherapy. For surgical treatment, because of its location deep into the pelvic cavity, the anatomy is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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