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Hydroxyl whole-protection didecyl quaternary ammonium with anti-tumor activity and preparation method thereof

A bis-decyl quaternary ammonium salt, full protection technology, applied in the field of synthesis of emodin derivatives, can solve the problems of high toxicity, poor water solubility of emodin, unclear biological activity mechanism and the like

Inactive Publication Date: 2011-01-12
FUZHOU UNIV
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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, poor biological activity, and the mechanism of biological activity is not very clear, so emodin has not been used in clinical reports.

Method used

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  • Hydroxyl whole-protection didecyl quaternary ammonium with anti-tumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0022] Get 1.6g (5.8mmol) emodin and dissolve in 120ml acetone, add 12g (87mmol) anhydrous potassium carbonate, slowly add dropwise 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 a yellow powder crude product, separated by silica gel column chromatography to obtain 1.52g of bright yellow solid, yield 82.6%. product structure 1 Confirmed by H NMR, IR, melting point. mid product 2 The characterization data are as follows:

[0023] m.p. 226~228℃; IR(KBr) ν 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), 6.78(d, 1H, J =2.0Hz, Ar-H), 4.00(s, 3H, OCH 3 ), 3.97(s, 3H, OCH 3 ), 3.96(s, 3H, ...

Embodiment 2

[0024] Embodiment 2: intermediate product 2 Synthesis of (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)b

[0025] Get 1.6g (5.9mmol) emodin and dissolve in 200ml acetone, add 10g (73mmol) anhydrous potassium carbonate, slowly add dropwise 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 bright yellow solid, yield 72.8%.

Embodiment 3

[0026] Embodiment 3: intermediate product 2 Synthesis of (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)c

[0027] Get 1.6g (5.9mmol) emodin and dissolve in 180ml acetone, add 10g (73mmol) anhydrous potassium carbonate, slowly add dropwise 4ml (43mmol) of (CH 3 O) 2 SO 2 , refluxed for 20 h, cooled to room temperature, concentrated solution, added 60 ml of water and stirred for 30 min, filtered with suction, washed with a small amount of cold acetone to obtain a yellow powder crude product, separated by silica gel column chromatography to obtain 1.30 g of bright yellow solid, yield 70.6%.

[0028]

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Abstract

The invention relates to synthesis of an emodin derivant with an anti-tumor function, in particular to a hydroxyl whole-protection didecyl quaternary ammonium with anti-tumor activity and a preparation method thereof. The didecyl quaternary ammonium is decyldimethylchlorosilane-[2-(4,5,7-trimethoxy-9,10-anthraquinonyl)methyl]. The preparation method is characterized by taking emodin as a raw material to carry out a series of synthetic reaction. The emodin derivant of the invention has proliferation inhibition action of different degrees on liver cancer HepG2, gastric cancer BGC, neuroma SH-SY5Y, gastric cancer AGS, cervical cancer Hela and the like as well as normal human embryonic lung fibroblast HELP and can be used for preparing medicines for treating cancers.

Description

technical field [0001] The present invention relates to the synthesis of a class of emodin derivatives with anticancer function, more specifically to a kind of double decyl quaternary ammonium salt with anticancer activity and fully protected hydroxyl group and its preparation method. technical background [0002] Emodin is an anthraquinone compound with a high content in Polygonaceae plants, which has various biological activities, such as anti-infection, anti-virus, immunosuppression, liver protection, anti-tumor, inhibition of cell proliferation, induction of cell apoptosis, prevention of Tumor metastasis and inhibition of protein kinases, etc. However, emodin itself has poor water solubility, high toxicity, insufficient biological activity, and the mechanism of biological activity is not very clear, so emodin has not been used in clinical reports. Therefore, it is very necessary to chemically modify emodin to improve anticancer activity. Contents of the invention [...

Claims

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Application Information

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IPC IPC(8): C07C225/24C07C221/00A61K31/14A61P35/00
Inventor 邵敬伟王文峰
Owner FUZHOU UNIV
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