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3-alkoxyl-6-carboxyl rhein or officinal salt thereof and preparation method and application thereof

A technology of alkoxyemodin ether and alkoxyl, which is applied in the field of emodin derivatives, can solve the problems that have not yet been seen in the research reports on the preparation method and application of 3-alkoxyl-6-carboxyrhein, and achieve Good development and application prospects, high product yield, strong antibacterial effect

Inactive Publication Date: 2009-12-30
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are no research reports on 3-alkoxyl-6-carboxyrhein or its pharmaceutically acceptable salts and their preparation methods and applications

Method used

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  • 3-alkoxyl-6-carboxyl rhein or officinal salt thereof and preparation method and application thereof
  • 3-alkoxyl-6-carboxyl rhein or officinal salt thereof and preparation method and application thereof
  • 3-alkoxyl-6-carboxyl rhein or officinal salt thereof and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1,3-alkoxy-6-carboxyrhein

[0030] Include the following steps:

[0031] The preparation of a, 3-alkoxyemodin ether

[0032] Weigh 5mmol of emodin and 6mmol of sodium carbonate, add 50ml of DMF, stir to dissolve, add dropwise a mixture of 5-15mmol of haloalkane and 50ml of DMF. ) method to monitor the reaction process, after the reaction, adjust the pH to 8~9 with the sodium carbonate solution of 2.5% with the mass percentage concentration, suction filtration, the filter cake is washed with the sodium carbonate solution of 2.5% with the mass percentage concentration, ethyl acetate weighs Crystallize and dry to obtain 3-alkoxyemodin ether. See Table 1 for the preparation of some 3-alkoxyemodin ethers.

[0033] Table 1, the preparation situation of part 3-alkoxyemodin ether

[0034]

[0035] Continued Table 1

[0036]

[0037] b. Preparation of 3-alkoxy-1,8-diacetylemodin ether

[0038] Weigh 0.5mmol of the 3-alkoxyemodin ether ob...

Embodiment 2

[0055] The preparation of embodiment 2,3-alkoxy-6-carboxyrheinate

[0056] Weigh 0.005 mol of 3-alkoxy-6-carboxyrhein obtained in Example 1, add equimolar alkali solution, and stir for reaction to obtain 3-alkoxyl-6-carboxyrheinate. See Table 5 for the preparation of some 3-alkoxyl-6-carboxyrheinates.

[0057] Table 5, the preparation situation of part 3-alkoxy-6-carboxyrheinate

[0058]

[0059]According to the method described in Example 1 or 2, the 3-alkoxy-6-carboxyrhein of the present invention or its pharmaceutically acceptable salt can be obtained by using a haloalkane with a carbon number of 1 to 24, and the structure of the product is determined by ultraviolet spectroscopy. (UV), infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy (NMR) for confirmation. The following are some structural characterization results of 3-alkoxy-6-carboxyrhein:

[0060] 3-butoxy-6-carboxyrhein: orange crystals, m.p.260~261.5℃; IR(KBr)υ: 3467, 3100, 2961, 1702, 1626...

experiment example 1

[0065] Antibacterial activity detection of experimental example 1, 3-alkoxy-6-carboxyrhein or its pharmaceutically acceptable salt

[0066] Emodin or 3-alkoxyl-6-carboxyrhein or 3-alkoxyl-6-carboxyrheinate were dissolved in water respectively to make a solution with a concentration of 1000ppm / ml as the test solution; 0.5ml of product solution, half-diluted with MH broth, the dilutions were 1:2, 1:4, 1:8, 1:16, 1:32, 1:64, 1:128, 1:256, 1:512; at the same time, a negative control without adding the test solution was set; each group was added with a titer of 10 8 cfu / ml Staphylococcus aureus or Escherichia coli bacterial solution 0.05ml, mixed evenly, cultured at 37°C for 24 hours, and tested the minimum inhibitory concentration (MIC).

[0067] The results are shown in Table 6. The minimum inhibitory concentrations of 3-alkoxyl-6-carboxyrhein are lower than emodin, especially 3-octyloxyl-6-carboxyrhein or its pharmaceutically acceptable salts. The bacterial concentration is 1 / ...

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Abstract

The invention discloses a 3-alkoxyl-6-carboxyl rhein with a general formula of (I) or an officinal salt thereof, and a preparation method and an application thereof. In the formula, R is straight-chain or branched-chain alkyl with 1-24 of carbon atoms. The preparation method comprises the following steps: positioning emodin and haloalkane in a solution for reaction in the presence of alkali so asto obtain 3-alkoxyl emodin ether; causing the 3-alkoxyl emodin ether to react with acetic oxide under the catalyzing of the alkali so as to obtain 3-alkoxyl-1,8-diacetyl emodin ether; causing the 3-alkoxyl-1,8-diacetyl emodin ether to react with oxidizer so as to obtain 3-alkoxyl-1,8-diacetyl-6-carboxyl rhein; and finally, causing the 3-alkoxyl-1,8-diacetyl-6-carboxyl rhein to react with the alkali to remove acetyl, and adding acid for acidification so as to obtain the 3-alkoxyl-6-carboxyl rhein. Compared with the emodin, the 3-alkoxyl-6-carboxyl rhein or the officinal salt thereof has a higher activity in antibacterium, blood fat reduction and blood sugar level reduction. In addition, the 3-alkoxyl-6-carboxyl rhein or the officinal salt thereof has simple preparation method, high productyield rate and low preparation cost and can be used for preparing highly-effective and safe drugs with the functions of antibacterium, blood fat reduction and blood sugar level reduction.

Description

technical field [0001] The invention relates to an emodin derivative, in particular to 3-alkoxyl-6-carboxyrhein or its pharmaceutically acceptable salt, and also relates to the preparation method and application of the compound or its pharmaceutically acceptable salt. Background technique [0002] Finding out valuable new drugs and lead compounds from the active ingredients of Chinese herbal medicines and modifying their structures is one of the directions of current drug research. Rhubarb is the dried root and rhizome of Rheum palmatum L., Rheum tanguticum Maxim.ex Balf., or medicinal Rheum officinale Baill. of the Polygonaceae plant; it is bitter in taste and cold in nature; it belongs to the spleen, stomach, large intestine, and liver , Pericardium Meridian; It has the effects of purging heat and dredging intestines, cooling blood and detoxification, and removing blood stasis to stimulate menstruation. Modern pharmaceutical research has found that the active ingredients ...

Claims

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Application Information

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IPC IPC(8): C07C65/40C07C51/16A61K31/192A61P31/00A61P3/06A61P3/10
Inventor 李学刚朱小康叶小利
Owner SOUTHWEST UNIVERSITY
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