Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof

An anti-tumor activity, thiourea arsenic sugar technology, applied in the field of arsenic sugar, can solve the problems of reduced yield, easy oxidation of intermediates, etc., and achieves the effects of simple reaction operation, high yield and good anti-tumor activity

Active Publication Date: 2020-03-24
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The organic arsenic sugar after deprotection, the intermediate is easy to oxidize and polymerize during the purification process, resulting in a decrease in yield

Method used

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  • Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof
  • Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof
  • Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1-(N-(4'-(1",3",2"-dithiarsen-2-yl)phenyl)-thiourea)-2,3,4,6-O-acetyl - Preparation of β-D-glucose (I):

[0032] 1) Preparation of 4-aminophenyl arsenous acid

[0033] a. Weigh 4-aminophenylarsenic acid (5g, 23mmol), potassium iodide (25mg, 0.15mmol) and dissolve it in a mixed solution of methanol / concentrated hydrochloric acid (30mL / 24mL), cool down to 0°C, and add SO 2 Gas for 30min until the solution turns from orange red to light yellow. The solution was kept in the refrigerator at 0°C overnight, filtered with suction, and the filter cake was washed twice with 25 mL of cold diethyl ether to obtain 4-dichloroarsenoaniline hydrochloride (6.2 g, 93.7%);

[0034] b. Dissolve 4-dichloroarsenoaniline hydrochloride (6.2g, 93.7%) in 150mL aqueous solution, cool down to 0-5°C, add 10 mol / L concentrated ammonia water in batches, to a total of 26mL, stir for 30 minutes, A white solid was precipitated, the solution was kept at 0-5°C overnight, filtered, the filter cake was w...

Embodiment 2

[0046] 1-(N-(4'-(1",3",2"-dithiarsen-2-yl)phenyl)-thiourea)-2,3,4,6-O-acetyl - Preparation of β-D-glucose (II):

[0047] 1) Preparation of 4-aminophenyl arsenous acid

[0048] a. Weigh 4-aminophenylarsenic acid (5g, 23mmol), potassium iodide (25mg, 0.15mmol) and dissolve it in a mixed solution of methanol / concentrated hydrochloric acid (30mL / 24mL), cool down to 0°C, and add SO 2 Gas for 30min until the solution turns from orange red to light yellow. The solution was kept in the refrigerator at 0°C overnight, filtered with suction, and the filter cake was washed twice with 25 mL of cold diethyl ether to obtain 4-dichloroarsenoaniline hydrochloride (6.2 g, 93.7%);

[0049] b. Dissolve 4-dichloroarsenoaniline hydrochloride (6.2g, 93.7%) in 150mL aqueous solution, cool down to 0-5°C, add 10 mol / L concentrated ammonia water in batches, to a total of 26mL, stir for 30 minutes, A white solid was precipitated, the solution was kept at 0-5°C overnight, filtered, the filter cake was ...

Embodiment 3

[0061] Example 3 Influence of the above-mentioned compounds I and II on the inhibitory effect of liver cancer cells HepG2

[0062] experimental method:

[0063] 1. Dilute hepatoma cell HepG2 to 1×10 6 / mL of cell suspension, take 100uL and inoculate in a 96-well plate

[0064] 2. After the cells adhered to the wall, the medium (DMEM, 10% FBS) was aspirated, and different concentrations of compound I or II were added to the 96-well plate (medium dilution), and the culture was continued for 48 hours.

[0065] 3. Add 10uL (5mg / mL) MTT solution (diluted in PBS) to each well and continue to incubate for 4h

[0066] 4. Aspirate the medium and add 150uL DMSO to each well

[0067] 5. Shake on a shaker for 10 minutes, and detect the absorbance at 490nm with a microplate reader

[0068] 6. Cell survival rate=experimental group) / blank group (blank group: no drug added), each group was parallelized three times, and the IC was calculated 50 .

[0069] Compound I:IC 50 = 7.62 ± 0.10 ...

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Abstract

The invention relates to the field of arsenic sugar, and in particular relates to thiourea-containing arsenic sugar with anti-tumor activity and a preparation method and application thereof. The thiourea-containing arsenic sugar is composed of two compounds: 1-(N-(4'-(1'', 3'', 2''-dithiaarsenic pentane-2-yl) phenyl)-thiourea)-2, 3, 4, 6-O-acetyl-beta-D-glucose and 1-(N-(4'-(1'', 3 '', 2''-dithiaarsenic hexane-2-yl) phenyl)-thiourea)-2, 3, 4, 6-O-acetyl-beta-D-glucose. The thiourea-containing arsenic sugar provided by the invention has the advantages of simple reaction operation and high yield. The thiourea-containing arsenic sugar with a specific three-dimensional configuration can be obtained, and the thiourea-containing arsenic sugar has good anti-tumor activity.

Description

technical field [0001] The invention relates to the field of arsenic sugar, in particular to a thiourea-containing arsenic sugar with antitumor activity, a preparation method and application thereof. Background technique [0002] Arsenic sugar has good anti-tumor activity, and the derivatives of chitosan - 2-glucosamine and its derivatives can reduce the toxicity of organic arsenic compounds, 1,3,4,6-O-acetyl-2 -Amino-D-glucose has an obvious effect in reducing the toxicity of organic arsenic. Using arsanic acid as raw material, it is reduced by sulfur dioxide, hydrochloric acid is salified, alkalized, and protective group is used to prepare the original, hydrochloric acid is salified, alkalized, and protective group is prepared4 -(1,3,2-Dithioarsane)aniline, and then react with propargyl acid to generate N-(4-(1,3,2-dithio Arsane)phenyl)alkynoyl gum: 2-azido-1,3,4,6-0-acetyl-D-glucose and N-(4-(1,3,2-disulfarsane)benzene N-(4"-arsenyl oxide phenyl)-1-(1",3",4',6'-O-acetyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H23/00C07H1/00A61P35/00A61K31/7135
CPCA61P35/00C07H1/00C07H23/00
Inventor 付伯桥曹祯毛重阳覃彩芹夏彩芬
Owner HUBEI ENG UNIV
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