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1,4‑Dihydroxyanthraquinone bisbenzyl quaternary ammonium salt with water solubility and anticancer activity

A technology of hydroxyanthraquinone bisbenzyl and anthraquinone benzyl bromide quaternary ammonium salt is applied in the field of 1,4-dihydroxyanthraquinone bisbenzyl quaternary ammonium salt and its preparation, which can solve the problems of cancer cell apoptosis and achieve The effect of simple synthesis steps, low toxicity, and easy transport

Inactive Publication Date: 2017-05-10
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Mitochondria are the main organelles that execute the apoptosis program, but the inner membrane of mitochondria is highly fat-soluble, and drugs with strong water solubility are usually difficult to pass through the inner membrane of mitochondria to induce apoptosis in cancer cells

Method used

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  • 1,4‑Dihydroxyanthraquinone bisbenzyl quaternary ammonium salt with water solubility and anticancer activity
  • 1,4‑Dihydroxyanthraquinone bisbenzyl quaternary ammonium salt with water solubility and anticancer activity
  • 1,4‑Dihydroxyanthraquinone bisbenzyl quaternary ammonium salt with water solubility and anticancer activity

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Experimental program
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Embodiment 1

[0023] 1) Synthesis of anthraquinone dibenzyl bromide

[0024] Add 1.5034 g (5.70 mmol) p-dibenzyl bromide (trade name α,α´-dibromo-p-xylene), 200 mg (1.45 mmol) K 2 CO 3 and 70 mL of acetone, stirred and heated to reflux under nitrogen protection; at the same time, 0.2003 g (0.83 mmol) of 1,4-dihydroxyanthraquinone, 300 mg (2.17 mmol) of K 2 CO 3 and 70mL of acetone, plug the bottle tightly with a hollow stopper (to prevent oxidation), heat it in a water bath, and shake it while heating. You can observe a lot of bubbles coming out, and the air must be continuously released in the middle. When there are no bubbles escaping, transfer the liquid part into the constant pressure funnel, and slowly add it dropwise to the three-necked bottle. After 24 h of reaction, a yellow clear liquid was obtained, which was poured into 500 mL of water, stirred at room temperature for 1 h, filtered with a Buchner funnel, and an orange-red solid was obtained after drying; the solid was washed w...

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Abstract

The invention discloses 1,4-dihydroxy anthraquinone bisbenzyl quaternary ammonium salt having water solubility and anticancer activity and preparation thereof. Particularly, the preparation comprises the steps: 1,4-dihydroxy anthraquinone is subjected to a reaction with excessive p-dibenzyl bromide to obtain anthraquinone dibenzyl bromide; the anthraquinone dibenzyl bromide is subjected to a reaction with N-methyldi-n-octylamine to obtain anthraquinone benzyl bromide quaternary ammonium salt; then the anthraquinone benzyl bromide quaternary ammonium salt is subjected to a reaction with triethanolamine to obtain the corresponding hydroxy anthraquinone bisquaternary ammonium salt. The anthraquinone bisquaternary ammonium salt has relatively good inhibition ability to a variety of cancer cells while maintaining water solubility. The compound which has both water solubility and anticancer activity is expected to be developed as an anticancer drug and has good application prospects.

Description

technical field [0001] The invention belongs to the field of preparation of quaternary ammonium salt anticancer drugs, in particular to a 1,4-dihydroxyanthraquinone bisbenzyl quaternary ammonium salt with water solubility and anticancer activity and its preparation. Background technique [0002] Quaternary ammonium salt anticancer drugs have the function of targeting the mitochondria of cancer cells, because the mitochondrial membrane potential of cancer cells is generally higher than that of normal cells, so positively charged quaternary ammonium salt anticancer drugs are easily enriched in the mitochondrial matrix of cancer cells . Mitochondria are the main organelles that execute the apoptosis program, but the inner membrane of mitochondria is highly fat-soluble, and drugs with strong water solubility are usually difficult to pass through the inner membrane of mitochondria to induce apoptosis in cancer cells. There are many examples of drug molecules losing anticancer ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/48C07C213/04A61P35/00A61P35/02
CPCC07C46/00C07C213/04C07C217/48C07C50/34
Inventor 王文峰胡秀芳苗军卫谢世波
Owner FUZHOU UNIV