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Arsenic sugar compound with anti-tumor activity and preparation method therefor and application thereof

A synthesis method and reaction technology, applied to arsenic sugar compound with anti-tumor activity and its preparation method and application field, capable of solving the problems of high cytotoxicity and the like

Active Publication Date: 2015-12-23
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in the literature that trivalent arsenic compounds have good antitumor activity, but are highly cytotoxic

Method used

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  • Arsenic sugar compound with anti-tumor activity and preparation method therefor and application thereof

Examples

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Effect test

Embodiment 1

[0025] Example 1: Preparation of 4-(1,3,2-disulfarsane)aniline, using methanol as solvent. Through the first method, 4-dichloroarsenaniline hydrochloride is first prepared, and then hydrolyzed under the action of ammonia water to obtain 4-aminophenyl arsenic oxide (3-valent arsenic), and then reacted with 1,2-ethanedithiol to prepare 4-(1 ,3,2-Disulfurarsane) aniline. Weigh arsanic acid (p-aminobenzene arsenic acid) (10g, 46.08mmol), potassium iodide (50mg, 0.30) and dissolve in 60mL methanol and 48mL concentrated hydrochloric acid mixed solvent. Introduce sulfur dioxide gas for 30 minutes until the solution turns from orange red to light yellow. A white solid precipitated out. The solution cools down to 0 o C, let stand overnight. Suction filtration, the filter cake was washed twice with 50 mL of cold diethyl ether. 4-Dichloroarsenaniline hydrochloride (12.57 g, 95%) was obtained as a white solid.

[0026] 4-Dichloroarsenaniline hydrochloride (12.57g, 43.78mmol) was add...

Embodiment 2

[0028] Example 2: Preparation of 4-(1,3,2-disulfarsane)aniline, using methanol as solvent. 4-dichloroarsenaniline hydrochloride is firstly prepared by method 2, and 4-(1,3,2-disulfurarsenane) aniline is prepared by directly reacting with 1,2-ethanedithiol.

[0029] Weigh arsanic acid (p-aminobenzene arsenic acid) (10g, 46.08mmol), potassium iodide (50mg, 0.30) and dissolve in 60mL methanol and 48mL concentrated hydrochloric acid mixed solvent. Introduce sulfur dioxide gas for 30 minutes until the solution turns from orange red to light yellow. A white solid precipitated out. The solution cools down to 0 o C, let stand overnight. Suction filtration, the filter cake was washed twice with 50 mL of cold diethyl ether. 4-Dichloroarsenaniline hydrochloride (12.57 g, 95%) was obtained as a white solid.

[0030] 4-Dichloroarsenaniline hydrochloride (12.57g, 57.96mmol) was dissolved in 300mL aqueous solution, cooled to 0-5 o C, adding sodium carbonate (total 10.65 g, 57.96 mmol) ...

Embodiment 3

[0031] Example 3: Using 4-(1,3,2-disulfarsane)aniline as raw material and dichloromethane as solvent. It can generate N-(4-(1,3,2-disulfarsane)phenyl)alkynamide with propargyl acid under the action of N,N'-cyclohexylcarbodiimide.

[0032] Add propargyl acid (216uL, 3.521mmol) into dichloromethane (10mL) dissolved in N,N'-cyclohexylcarbodiimide (726.5mg, 3.521mmol), stir at room temperature for 1 hour, cool down in an ice bath and stir After 30 min (1,3,2-disulfarsane)aniline (760.6 mg, 2.934 mmol) in dichloromethane (10 mL) was added dropwise. After the dropwise addition was completed, the reaction was incubated for 30 min, and the temperature was gradually raised to room temperature for overnight reaction. The reaction is complete. Celite was filtered, the solvent was evaporated to dryness under reduced pressure, and the residue was subjected to column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) to obtain a yellow solid (584.5mg, 64%).

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Abstract

The invention discloses an arsenic sugar compound with anti-tumor activity and a preparation method therefor and application thereof. The invention relates to N-(4''-(1'',3'',2''-dithioarsine)phenyl)-1-(1',3',4',6'-O-acetyl-D-glucose)-1,2,3-triazole-4-formamide. The preparation method comprises: reducing arsanilic acid by sulfur dioxide, carrying out salification and alkalization by hydrochloric acid, adding a protecting group to prepare 4-(1,3,2-dithioarsine) aniline, and generating N-(4-(1,3,2-dithioarsine) phenyl) alkynyl amide with propargylic acid under the action of N, N'-cyclohexyl carbodiimide; carrying out a reaction on 2-azido-1,3,4,6-O-acetyl-D-glucose and N-(4-(1,3,2-dithioarsine)phenyl) alkynyl amide to generate N-(4''-arsenic oxide phenyl)-1-(1',3',4',6'-O-acetyl-D-glucose)-1,2,3-triazole-4-formamide; and carrying out a reaction on the obtained product and 1,2-dithioglycol to obtain the arsenic sugar compound provided by the invention.

Description

Technical field [0001] The present invention involves compounds with anti-tumor activity n- (4 "-(1", 3, 2 "-Mulflinane) -1- (1 ', 3', 4'-o-Acetyl-D-glucose) -1,2,3-triazol-4-methalmamide and its preparation methods and applications. [0002] The present invention provides a compound with good anti-rectal cancer activity n- (4 "-(1", 3, 2 "-2" -Mulflinane) -1- (1 ', 3', 4 ', 6', 6 ', 6', 6 '-O-acetyl-D-glucose) -1,2,3-triazol-4-methalmamide and its preparation methods and their applications. Background technique [0003] Rectal cancer refers to the cancer between the tooth line and the rectum sigmoid colon, which is one of the most common malignant tumors in the digestive tract.The position of rectal cancer is low, and it is easily diagnosed by the rectal pointer and sigmoid colonoscopy.At present, the treatment of rectal cancer needs to be based on surgery, supplemented by comprehensive treatment of chemotherapy and radiotherapy.For surgical treatment, due to its in -depth pelvi...

Claims

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Application Information

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IPC IPC(8): C07H23/00C07H1/00A61P35/00A61P1/00
CPCY02P20/55
Inventor 付伯桥覃彩芹夏彩芬杨新河
Owner HUBEI ENG UNIV
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