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Method for synthesizing antitumor derivative apogossypolone by using gossypol acetate

An anti-tumor technology of gossypol acetate, applied in organic chemistry, quinone oxidation preparation, etc., to improve synthesis efficiency and yield, save time, and improve purity

Inactive Publication Date: 2008-07-23
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no similar report on the related patents on the synthesis of gossypol derivatives

Method used

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  • Method for synthesizing antitumor derivative apogossypolone by using gossypol acetate
  • Method for synthesizing antitumor derivative apogossypolone by using gossypol acetate
  • Method for synthesizing antitumor derivative apogossypolone by using gossypol acetate

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Embodiment 1

[0026] Weigh 5 grams of gossypol acetate with a balance, add 15 ml of 20% sodium hydroxide, and stir at 60°C for 300 minutes. After the reaction, place the reactor in ice water and add 15 ml of 85% concentrated sulfuric acid. Extract with diethyl ether two to three times, and concentrate to dryness in vacuo to obtain about 4.8 g of the initial product I, which is gray-green in color. Dissolve the initial product I with 9.6ml of dioxane, add 4.8ml of acetic anhydride, stir the reaction at 50°C for 120 minutes, cool to room temperature and let it stand for 30 minutes, extract 2-3 times with ethyl acetate, and concentrate in vacuo To dryness, recrystallization and purification with ethyl acetate / n-hexane (volume ratio 1:1) gave 3.6 g of pure product II with pale yellow color. Dissolve product II with 18ml of glacial acetic acid, add 3.6g of oxidant periodate, react at 60°C for 120 minutes, cool to room temperature and extract 2-3 times with ethyl acetate, concentrate to dryness u...

Embodiment 2

[0028] Weigh 5 grams of gossypol acetate with a balance, add 30 ml of 35% sodium hydroxide, and stir and react at 90°C for 165 minutes. After the reaction, place the reactor in ice water and add 7 ml of 90% concentrated sulfuric acid. Extracted two to three times with ethyl acetate, and concentrated to dryness in vacuo to obtain about 4.6 g of the initial product, which was gray-green in color. Dissolve the initial product I with 30ml of dioxane, add 15ml of acetic anhydride, stir the reaction at 120°C for 90 minutes, cool to room temperature after the end and leave it for 75 minutes, extract 2-3 times with ether, concentrate to dryness under vacuum, use Ethyl acetate / n-hexane (volume ratio 1:3) was used for recrystallization and purification to obtain 3.6 g of pure product II with pale yellow color. Dissolve the product II with 120ml of glacial acetic acid, add 20g of oxidant periodate, react at 90°C for 60 minutes, cool to room temperature after the end and extract 2-3 times...

Embodiment 3

[0030] Weigh 5 grams of gossypol acetate with a balance, add 50 ml of 50% sodium hydroxide, and stir and react at 120°C for 30 minutes. After the reaction, place the reactor in ice water and add 1 ml of 98% concentrated sulfuric acid. Extracted two to three times with petroleum ether, and concentrated to dryness in vacuo to obtain about 4.8 g of the initial product I, which was gray-green in color. Dissolve the initial product I with 48ml of dioxane, add 24ml of acetic anhydride, stir the reaction at 200°C for 20 minutes, cool to room temperature after the end and let it stand for 120 minutes, extract 2-3 times with ethanol, concentrate to dryness under vacuum, use Ethyl acetate / n-hexane (1:6) was used for recrystallization and purification to obtain 3.6 g of pure product II with pale yellow color. Dissolve the product II with 180ml of glacial acetic acid, add 36 grams of oxidant periodate, react at 150°C for 5 minutes, cool to room temperature after the end and extract with e...

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Abstract

The invention discloses a method using gossypol acetic acid to synthesize the antitumor derivative of Apogossypolone, which comprises four steps as follows: the concentrated strong alkaline solution is added in the gossypol acetic acid for reaction under a certain temperature to obtain the product of Apogossypol after removing aldehyde group; the protective agent is added in the Apogossypol according to a certain proportion for reaction under a proper temperature to obtain the product of Hexa-acetylapogossypol; the oxidant is added for oxidation of the Hexa-acetylapogossypol under a proper temperature, and the product of Tetra-acetylapogossypol is obtained after reaction; and the de-protection agent is added for de-protection of the Tetra-acetylapogossypol to obtain the product of Apogossypolone with the molecular weight being 490 and the color being brick red. The synthesizing method of the antitumor derivative of Apogossypolone by using gossypol acetic acid has the advantages that the structure of the natural drug of gossypol acetic acid is changed via the four steps of chemical reactions; and compared with the natural gossypol acetic acid, the obtained product of Apogossypolone has the characteristics of small molecular weight, better stability and higher antitumor activity.

Description

technical field [0001] The invention relates to a method for synthesizing anti-tumor derivative Apogossypolone with gossypol acetate. Background technique [0002] Gossypol is a natural biphenyl compound extracted from cottonseed. In the 1980s, gossypol was found to have anti-tumor activity. Although its precise mechanism of action has not been studied clearly, gossypol is different from other conventional anticancer drugs. It shows strong binding ability to several important enzymes and has obvious inhibitory effect on cancer cells. Recent studies have shown that L-gossypol and its homologues are effective inhibitors of Bcl-2 / Mc1-1 protein and have very high anticancer activity. [0003] So far, three sets of clinical trials have been conducted in the United States on human metastatic cancer cells (such as glioma, adrenal tumor and breast cancer) to test the therapeutic effect of gossypol. At the same time, studies have also shown that the activity of L-gossypol in inhib...

Claims

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Application Information

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IPC IPC(8): C07C50/32C07C46/06
Inventor 吴道澄詹勇华徐梁
Owner XI AN JIAOTONG UNIV
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