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Emodin di-n-octyl quaternary ammonium salt with anti-leukemia activity and preparation method thereof

A technology of n-octyl quaternary ammonium salt and methyl di-n-octyl, which is applied in the field of emodin di-n-octyl quaternary ammonium salt and its preparation, can solve the problems of broken cancer cell growth, poor water solubility and high toxicity, and achieve The preparation process is simple, the yield is high, and the preparation conditions are mild

Active Publication Date: 2012-08-29
FUJIAN MEDICAL UNIV UNION HOSPITAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, emodin itself has poor water solubility, high toxicity, insufficient biological activity, and the anti-cancer mechanism is not very clear. At present, it is only speculated that it mainly depends on its planar structure embedded in the DNA double helix structure and interferes with DNA replication to disrupt the growth of cancer cells.
At present, emodin has not been used in clinical reports

Method used

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  • Emodin di-n-octyl quaternary ammonium salt with anti-leukemia activity and preparation method thereof
  • Emodin di-n-octyl quaternary ammonium salt with anti-leukemia activity and preparation method thereof
  • Emodin di-n-octyl quaternary ammonium salt with anti-leukemia activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: Synthesis of intermediate product 2 (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)——(a)

[0019] Get 1.6g (5.8mmol) of emodin and dissolve in 120ml of acetone, add 12g (87mmol) of anhydrous potassium carbonate, and slowly add 8ml (87mmol) of (CH 3 O) 2 SO 2 , refluxed for 24h, cooled to room temperature, concentrated solution, added 100ml of water and stirred for 30min, suction filtered, washed with a small amount of cold acetone to obtain the crude product of yellow powder, separated by silica gel column chromatography to obtain 1.52g of bright yellow solid, the silica gel column chromatography The eluent is dichloromethane, and the yield is 82.6%. product structure 1 Confirmed by H NMR, IR, melting point. The characterization data for Intermediate 2 are as follows:

[0020] m.p.226~228℃; IR(KBr)v max / cm-1 : 2941, 2843, 1662, 1601, 1322, 1241, 1022, 759. 1 HNMR (400MHz, CDCl 3 ), δ: 7.65(s, 1H, Ar-H), 7.34(d, 1H, J=2.4Hz, Ar-H), 7.11(s, 1H, Ar-H),...

Embodiment 2

[0021] Example 2: Synthesis of intermediate product 2 (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)——(b)

[0022] Get 1.6g (5.9mmol) of emodin and dissolve in 200ml of acetone, add 10g (73mmol) of anhydrous potassium carbonate, and slowly add 4ml (43mmol) of (CH 3 O) 2 SO 2 , refluxed for 24h, cooled to room temperature, concentrated solution, added 80ml of water and stirred for 30min, suction filtered, washed with a small amount of cold acetone to obtain a yellow powder crude product, separated by silica gel column chromatography to obtain 1.34g of a bright yellow solid (intermediate product 2), the The eluent of the silica gel column chromatography is dichloromethane, and the yield is 72.8%.

Embodiment 3

[0023] Example 3: Synthesis of intermediate product 2 (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)——(c)

[0024] Get 1.6g (5.9mmol) emodin and dissolve in 180ml acetone, add 10g (73mmol) anhydrous potassium carbonate, slowly add 4ml (43mmol) of (CH 3 O) 2 SO 2 , refluxed for 20h, cooled to room temperature, concentrated the solution, added 60ml of water and stirred for 30min, suction filtered, washed with a small amount of cold acetone to obtain the crude product of yellow powder, separated by silica gel column chromatography to obtain 1.30g of bright yellow solid (intermediate product 2), the obtained The eluent of the silica gel column chromatography is dichloromethane, and the yield is 70.6%.

[0025] Known by embodiment 1-3, emodin adds anhydrous potassium carbonate and (CH 3 O) 2 SO 2 The chemical reaction can obtain the intermediate product 2 (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone) with a yield of more than 70%.

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Abstract

The invention discloses an emodin di-n-octyl quaternary ammonium salt with anti-leukemia activity and a preparation method thereof. The emodin di-n-octyl quaternary ammonium salt is methyl di-n-octyl-[2-(4,5-dihydroxyl-7-methoxyl-9,10-anthraquinonyl) methyl] ammonium salt. Experiments prove that an emodin derivative, i.e. the emodin di-n-octyl quaternary ammonium salt has proliferation inhibition effects of different degrees on four leukemia cell lines K562, NB4, U937 and Jurkat and can be used for preparing a medicament for treating leukemia. The emodin derivative methyl di-n-octyl-[2-(4,5-dihydroxyl-7-methoxyl-9,10-anthraquinonyl) methyl] ammonium bromide has the advantages of simple preparation process, mild preparation conditions and high yield of reaching up to over 50 percent; and in-vitro cancer cell inhibition experiments show that the four leukemia cell lines K562, NB4, U937 and Jurkat can be effectively killed off.

Description

technical field [0001] The invention belongs to the pharmaceutical field of emodin derivatives with anti-leukemia function, and more specifically relates to an emodin di-n-octyl quaternary ammonium salt with anti-leukemia activity and a preparation method thereof. technical background [0002] Emodin is an anthraquinone compound with a relatively high content in Polygonaceae plants. It has inhibitory effects on dozens of cancer cells such as leukemia, gastric cancer, liver cancer, and pancreatic cancer. It can be called a natural anti-cancer star. However, emodin itself has poor water solubility, high toxicity, insufficient biological activity, and the anti-cancer mechanism is not very clear. At present, it is only speculated that it mainly depends on its planar structure embedded in the DNA double helix structure and interferes with DNA replication to disrupt the growth of cancer cells. At present, emodin has not been used in clinical reports. In order to further clarify t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/63C07C209/12A61K31/14A61P35/02
Inventor 胡建达王文峰
Owner FUJIAN MEDICAL UNIV UNION HOSPITAL
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