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3-o-(p-methylsulfonate benzyl)ascorbic acid with anticancer activity and preparation method

A technology of ascorbic acid and mesylate, applied in the field of medical drugs, can solve the problems of single administration route, poor patient compliance, loss of activity, etc., achieve good clinical application value, and significantly inhibit activity

Active Publication Date: 2019-09-03
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, more and more reports have proved that large doses of ascorbic acid can be used to treat cancer to a certain extent, but it is difficult to achieve high plasma ascorbic acid concentration through oral administration, and can only rely on intravenous injection, single route of administration and patient compliance poor
In addition, due to the presence of polyhydroxyl groups in the structure of ascorbic acid, the structure is unstable, and it is easily oxidized and inactivated in vitro.

Method used

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  • 3-o-(p-methylsulfonate benzyl)ascorbic acid with anticancer activity and preparation method
  • 3-o-(p-methylsulfonate benzyl)ascorbic acid with anticancer activity and preparation method
  • 3-o-(p-methylsulfonate benzyl)ascorbic acid with anticancer activity and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1. 4-((methylsulfonyl)oxy) benzyl mesylate (Ms-HBA-ASA) synthesis

[0018] Add 25ml of dichloromethane into a 100ml three-necked flask equipped with a reflux condenser, turn on the constant temperature oil bath and magnetic stirrer, then add 2.5g of p-hydroxybenzyl alcohol (HBA), add 7ml of triethylamine, and heat Heat and stir until the p-hydroxybenzyl alcohol dissolves. 7.5 g of methanesulfonic anhydride (MsOMs) were dissolved in 15 ml of dichloromethane solution. Remove the oil bath and add methanesulfonic anhydride dichloromethane dropwise under an ice bath environment. After the dropwise addition, remove the ice bath, change to 25 ° C oil bath heating, magnetic stirring reaction for 4 to 6 hours, after the reaction, the reaction solution was washed three times with water, the concentrated organic layer was collected, and column chromatography (petroleum ether: ethyl acetate = 2:1) separation, vacuum rotary evaporation, and concentration to obtain 5.19 ...

Embodiment 2

[0019] Example 2. 3-O-(p-methylsulfonate benzyl)ascorbic acid (Ms-HBA-ASA)

[0020] Add 25ml of ethanol to a 100ml three-neck flask, turn on the constant temperature oil bath and magnetic stirrer, add 2g of ascorbic acid, add 1.74ml of triethylamine, protect with nitrogen, then add 3.5g of Ms-HBA-Ms, and heat at 25°C Stir the reaction for 1 to 3 hours, separate the reaction solution by column chromatography (dichloromethane:methanol=30:1), evaporate in vacuo, and concentrate to obtain a white solid that is 3-O-(p-methylsulfonate benzyl)ascorbic acid (Ms-HBA-ASA) 3.52g, reaction yield 86%. The structure of the product was characterized by H NMR and mass spectrometry (see Figure 1-2 ).

Embodiment 3

[0021] Example 3. Cancer cell inhibition test of 3-O-(p-methylsulfonate benzyl) ascorbic acid

[0022] Cytotoxicity was evaluated by MTT method. Human colon cancer cell line RKO, human lung cancer cell line A549, human breast cancer cell line MDA-231 and human melanoma cell line B16-F10 were inoculated in 96-well plates at appropriate concentrations, each well The total volume is 200ul. After culturing for 24 hours, discard the culture medium, add 200ul of culture medium with different drug concentrations, and set up a solvent control group at the same time. After 72 hours of drug action, add 50ul of 1mg / ml MTT solution to each well, continue to cultivate for 4h, and remove the culture medium. solution, add 150ul DMSO to each hole, and after the color is completely dissolved, measure the absorbance value with a wavelength of 490nm with an enzyme-linked analyzer, and calculate the inhibitory rate of the drug on cell growth (see image 3 ). Calculation of IC by Bliss method 50...

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Abstract

The invention belongs to the technical field of medicines, and discloses a novel 3-O-(para-methanesulfonate benzyl)-ascorbic acid compound with anti-cancer activity and a preparation method thereof. The compound has the advantages that the synthesizing route is simple, the reaction condition is mild and environment-friendly, the yield is higher, and the good inhibiting activity on human colon cancer cell RKO, human lung cancer cell A549, human breast cancer cell MDA-231 and human melanoma cell B16-F10 is realized.

Description

technical field [0001] The invention belongs to the technical field of medical drugs, and in particular relates to a novel anticancer active compound 3-O-(p-methylsulfonate benzyl)ascorbic acid and a preparation method. Background technique [0002] Tumor is a new organism formed by the body under the action of various carcinogenic factors when a certain cell in a local tissue loses normal regulation of its growth at the gene level, resulting in abnormal clonal proliferation. Tumors are generally divided into two categories, benign and malignant, and all malignant tumors are collectively called cancer. At present, cancer has become the second cause of death in the world. In recent years, the incidence of cancer in my country has shown a parabolic rise, and the number of cases and deaths accounted for more than 25% of the global cancer. Among them, lung cancer and colon cancer have respectively occupied the top two places in the incidence of malignant tumors. Breast cancer ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/62A61K31/375A61P35/00
Inventor 栾立标胡思源
Owner CHINA PHARM UNIV