Setoglaucine salt, preparation method thereof and medicinal composition containing the same

A technology of Erianin salt and Erianin, which is applied in the directions of drug combinations, compounds of Group 5/15 elements of the periodic table, phosphorus organic compounds, etc. And other issues

Inactive Publication Date: 2007-02-07
ZHEJIANG TIANHUANG MEDICINAL PLANT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Due to the low water solubility of erianin, the solubility in water is only <1mg / ml, which limits its preparation performance and clinical application, so it is necessary to study the salts that can improve its water solubility
At present, there is no literature report about Erianin salt and its preparation method

Method used

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  • Setoglaucine salt, preparation method thereof and medicinal composition containing the same
  • Setoglaucine salt, preparation method thereof and medicinal composition containing the same
  • Setoglaucine salt, preparation method thereof and medicinal composition containing the same

Examples

Experimental program
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Effect test

preparation example Construction

[0129] 4. Preparation of benzyl-protected isovanillin (vi)

[0130] In a 250ml three-neck flask, add 15g (98.59mmol) of isovanillin (iv), 200ml of absolute ethanol, heat to 40°C to dissolve, add 9g (65.07mmol) of potassium carbonate, and add 15ml (130.13mmol) of benzyl chloride while stirring , heated to reflux for 1 hr, after TLC detected that the reaction was complete, cooled to 50°C, filtered while it was hot, cooled the filtrate in the refrigerator overnight, crystals precipitated, filtered with suction, washed the filter cake with 30ml of absolute ethanol, and dried in vacuo to obtain benzyl Protected isovanillin (vi), 19.72 g of white needle-like crystals, the yield is 82.56%.

[0131] The obtained product can be used for the next reaction without further purification. If you want to get the pure product, you can recrystallize it with absolute ethanol to get white columnar crystals.

[0132] 5. Preparation of cis-trans isomer (vii)

[0133] In a 250ml three-necked fla...

Embodiment 1

[0141] [Example 1] Preparation of Erianin Disodium Phosphate (directly converted into sodium salt)

[0142] 1. Phosphorylation reaction

[0143] In a 100ml round bottom flask, add 4.4ml (47.4mmol) of phosphorus oxychloride and 25ml of dichloromethane, and dropwise add a solution of 5g (15.7mmol) of erianin in 10ml of dichloromethane. After dripping, stir for 5 minutes. A solution of 3.3ml (23.8mmol) of triethylamine in 5ml of dichloromethane was added dropwise. Stir at room temperature for 3 hrs, TLC detection, after the reaction is complete, add 100 ml of cold water to quench. Fully oscillate to separate the organic phase; then wash with 50ml×2 water, extract the aqueous layer with dichloromethane, combine the organic layer, and dry it with an appropriate amount of anhydrous sodium sulfate overnight; filter with suction, evaporate the filtrate to remove the solvent under reduced pressure, and obtain a viscous liquid, namely For the crude acid chloride.

[0144] 2. Salt fo...

Embodiment 2

[0147] [Example 2] Preparation of Erianin Disodium Phosphate (need to generate phosphate intermediate)

[0148] 1. Synthesis of Erianin Dibenzyl Phosphate

[0149] In a dry three-necked flask protected by argon, dissolve Erianin (20g, 63.2mmol) in 200ml of acetonitrile, stir, cool to -25°C, add CCl 4(35ml, 316mmol), stirred for 5 minutes, diisopropylethylamine (23.13ml, 133mmol) was added dropwise with a syringe, then DMAP (772mg, 6.32mmol) was added dropwise, and dibenzyl phosphite was added dropwise after 1 minute (20.33ml, 92mmol), control the reaction temperature below -10°C, check with TLC after 1hr, if the reaction is complete, add 50ml of 0.5M KH 2 PO 4 , extracted with ethyl acetate 100ml×3, combined organic layers, washed with 100ml water, 100ml saturated NaCl, dried, and filtered. The solvent was drained to give a yellow oil. Column chromatography (ethyl acetate: hexane = 2: 3), recrystallization from ethyl acetate and hexane gave colorless needles, namely Eriani...

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PUM

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Abstract

The invention discloses a chaetocin salt and preparing method and drug composition with chaetocin salt, which possesses structure formula (I) on the right, wherein R is salt of inorganic oxyacid or organic monobasic acid group and metal, ammonium salt or organic amine. The invention improves solubility greatly, which prevents tumour effectively.

Description

technical field [0001] The present invention relates to erianin salt and its preparation method. [0002] The invention also relates to pharmaceutical compositions comprising such compounds. [0003] The invention also relates to the application of the erianin salt in the preparation of antitumor drugs. Background technique [0004] Cancer has become the second killer of humans next to cardiovascular disease. Currently commonly used methods of anti-cancer chemotherapy and radiotherapy can cause serious adverse reactions to the human body. Experts at home and abroad have found that the traditional Chinese medicine Dendrobium has anti-tumor, anti-aging and blood vessel expansion effects, and its ethanol extract and its bibenzyl compounds have different degrees of anti-tumor activity in vivo. The active ingredients of Dendrobium have attracted attention at home and abroad. [0005] The research results of Wang Tianshan et al. (In vitro test of the growth inhibitory effect o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/08C07C43/235A61P35/00
CPCC07C305/04C07F9/12A61P35/00
Inventor 李亦平唐建刚李宁
Owner ZHEJIANG TIANHUANG MEDICINAL PLANT PHARMA
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