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Sulfonyl ester group anthraquinone derivative, preparation method and application thereof

A technology of sulfonyl ester anthraquinones and derivatives, which is applied in the field of sulfonyl ester anthraquinone derivatives and their preparation methods and applications in pharmaceuticals, and can solve the problems that limit the wide application of anthracyclines, cardiomyocytes Toxicity and other problems, to achieve broad-spectrum anti-tumor activity, the effect of simple and easy preparation method

Active Publication Date: 2019-04-12
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, while anthracyclines have high-efficiency anticancer effects, they are also highly toxic to cardiomyocytes.
In addition, long-term use of anthracycline antitumor antibiotics is prone to drug resistance, including cross-resistance between this class of drugs and cross-resistance to vincristine, which limits the wide application of anthracyclines in clinical practice. application

Method used

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  • Sulfonyl ester group anthraquinone derivative, preparation method and application thereof
  • Sulfonyl ester group anthraquinone derivative, preparation method and application thereof
  • Sulfonyl ester group anthraquinone derivative, preparation method and application thereof

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preparation example Construction

[0036] 2. Preparation of sulfonyl ester anthraquinone derivatives The common raw material in the examples is 1,4-dihydroxy-9,10-anthraquinone, that is, 1,4-dihydroxyanthraquinone. The structure and atomic number of 1,4-dihydroxy-9,1-anthraquinone are as follows:

[0037]

[0038] Raw material chemical molecular structural formula (M01-M16) involved in the reaction process of table 2

[0039]

[0040]

Embodiment 1

[0041] The preparation of embodiment 1 sulfonyl ester group anthraquinone derivatives (C01-C16)

[0042] (1) Preparation of 1,4-bis(1,1'-biphenyl)-4-sulfonate)-9,10 anthraquinone (C01):

[0043] Add 0.5 g (2 mmol) of 1,4 dihydroxyanthraquinone, 1.2 g of excess 4-biphenylsulfonyl chloride, and 0.5 g of anhydrous potassium carbonate to a glass flask in sequence, then add 20 mL of anhydrous acetone, and react in an oil bath at 60°C Under reflux reaction, TLC monitors the reaction throughout the whole process. After the reaction is completed, add an appropriate amount of ice water to quench the reaction, filter to obtain a light yellow crude product, and purify it by silica gel column chromatography. Eluent: (dichloromethane:petroleum ether=1:2), The light yellow target compound was obtained with a yield of 74%.

[0044] (2) Preparation of 1,4-bis(2-naphthalenesulfonate)-9,10 anthraquinone (C02):

[0045] Add 0.5g (2mmol) of 1,4-dihydroxyanthraquinone, 1.4g of excess 2-naphthale...

Embodiment 2

[0074] The preparation of embodiment 2 sulfonyl ester group anthraquinone derivatives (C01-C16)

[0075] (1) Preparation of 1,4-bis(1,1'-biphenyl)-4-sulfonate)-9,10 anthraquinone (C01):

[0076] Add 0.1kg of 1,4-dihydroxyanthraquinone, 0.5kg of excess 4-biphenylsulfonyl chloride raw material, 0.1kg of anhydrous potassium carbonate, and then add 4L of anhydrous acetone in a stainless steel reaction kettle, and react in an oil bath at 60°C Reflux reaction, TLC monitors the reaction throughout the whole process, after the reaction is complete, add an appropriate amount of ice water to quench the reaction, filter to obtain a light yellow crude product, purify by silica gel column chromatography, eluent (dichloromethane:petroleum ether=1:2), and obtain pale yellow product Yellow target compound, yield 65%.

[0077] (2) Preparation of 1,4-bis(2-naphthalenesulfonate)-9,10 anthraquinone (C02):

[0078] Add 0.1kg (0.4mol) of 1,4-dihydroxyanthraquinone, 0.5kg of excess 2-naphthalenesu...

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Abstract

The invention discloses a sulfonyl ester group anthraquinone derivative, a preparation method and application thereof. The sulfonyl ester group anthraquinone derivative provided by the invention has good anti-tumor activity, has a median inhibitory concentration of less than 100micromol / mL on Hela, MCF-7, A549, CNE2 and other cell lines, and has no inhibition on normal cells. According to the invention, sulfonyl ester group is introduced to an anthraquinone parent nucleus to improve the water solubility and acidity and acid-base properties so as to improve the anti-tumor activity of anthraquinone compounds, and the preparation method is simple and feasible. The sulfonyl ester group anthraquinone derivative provided by the invention has wide potential applications in fluorescent materials,medicine, pesticides, materials, etc., and especially has application value in preparation of anticancer drugs.

Description

technical field [0001] The invention relates to anthraquinone derivatives, in particular to a sulfonyl ester anthraquinone derivative, a preparation method thereof and an application in pharmacy. Background technique [0002] Cancer is the main cause of threat to human health and death. About 10 million people are diagnosed with tumors every year, and due to the acceleration of the aging process, the incidence of cancer worldwide continues to rise. It is estimated that by 2020, there will be 16 million new cancer cases each year. At present, the treatment methods for tumors mainly include five categories: surgery, radiation therapy, chemotherapy, biological targeted therapy, and traditional Chinese medicine therapy, while biological targeted therapy and traditional Chinese medicine therapy are relatively seldom used. Surgical treatment is an important method to achieve the treatment of tumors by means of surgical resection of tumors. The effect of treating early tumors is o...

Claims

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Application Information

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IPC IPC(8): C07C309/75C07C309/73C07C309/74C07C303/28A61P35/00
CPCA61P35/00C07C309/73C07C309/74C07C309/75
Inventor 刘旭刘仰厚沈泓佑梁跃辉鲁素芳王立升江俊谢鹏
Owner GUANGXI UNIV
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