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Water-soluble arteannuin derivative and preparation method thereof

A water-soluble technology of artemisinin derivatives, applied in pharmaceutical formulations, drug combinations, allergic diseases, etc., can solve the problems of low oral bioavailability, short half-life, damage to the central nervous system, etc., to increase bioavailability , reduce toxic and side effects, and have novel synthetic ideas

Inactive Publication Date: 2008-10-29
CHONGQING UNIV
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, in animal experiments, it was found that when large doses of artemisinin and its derivatives are used for a long time, there may be two toxicological effects: damage to the central nervous system and changes in the electrocardiogram
Moreover, these drugs still have high relapse rates, short half-lives, and low oral bioavailability
Artesunate is unstable in water and must be dissolved in sodium bicarbonate to make sodium salt before use, which is inconvenient to use

Method used

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  • Water-soluble arteannuin derivative and preparation method thereof
  • Water-soluble arteannuin derivative and preparation method thereof
  • Water-soluble arteannuin derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1: the reduction of artemisinin

[0066] Add 2.81g (0.01mol) artemisinin, 0.454g (0.012mol) NaHB 4 And 10mL of anhydrous methanol stirred at room temperature for 24h. The filtrate was distilled under reduced pressure to recover methanol. The residue was dissolved in 250 mL of water, then extracted three times with 50 mL of ethyl acetate, the organic layer was washed with a small amount of water, and the water washings and the water layer were combined. It was extracted with ethyl acetate, and the organic layers were combined. Evaporate solvent, dry product-dihydroartemisinin (see figure 1 );

Embodiment 2

[0067] Example 2. Preparation of bromomannose per acetylpyranoside

[0068] Take 2.00 grams of D-mannose and add it to a three-neck flask containing 10 mL of acetic anhydride suspension (wherein acetic anhydride protects the hydroxyl on the sugar molecule to make it a stable ester), add 135 mg of iodine, and stir the reaction with magnetic force at room temperature Until the reaction system is brown and transparent (indicating that the full acetylation reaction is completed for about 5-30min), then the reaction mixture is diluted with 50mL of dry dichloromethane, and 14mL of 40% hydrogen bromide in glacial acetic acid solution is added under ice-cooling (addition of bromine Hydrogen, so that the sugar molecule with a -Br). After the addition, stir the reaction at room temperature until the reaction is detected by TCL (about 1-6h). The reaction mixture was diluted with 150 mL of dichloromethane, washed successively with ice water (60 mL×2), saturated sodium bicarbonate solutio...

Embodiment 3

[0069] Example 3. Preparation of D-mannose-artemisinin:

[0070] see figure 2 . Add the artemisinin reduction product dihydroartemisinin 1.354g that embodiment 1 obtains in the 100mL three-neck bottle that magnetic stirrer is housed, tetrabutylammonium hydrogensulfate 0.2g (tetrabutylammonium hydrogensulfate is a phase transfer catalyst ), distilled water 50mL, add potassium hydroxide 0.134g, adjust the pH of the solution to be 8-9. After stirring and refluxing for 4 hours, add 1.62 g of peracetylpyranobromomannose described in Example 2 to the reaction system, condense and reflux for 5 hours, cool, filter, and recrystallize the filter cake with diethyl ether and petroleum ether to obtain the present invention. Water-soluble artemisinin derivative - D-mannose - artemisinin.

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Abstract

The invention relates to a water-soluble arteannuin derivative and a preparation method thereof. The method comprises the following steps of: (1) preparing dihydroarteannuin; (2) preparing tetra-acetyl-mannopyranosyl bromide; and (3) preparing the water-soluble arteannuin derivative. The water-soluble arteannuin derivative is proven to have good water solubility, is easy for preparing preparations and has good pharmaceutical prospect after structural identification and water solubility analysis. The inventive preparation method has the advantages of simple operation, mild reaction conditions, and no need of deprotection step. After initial cell experiments, the water-soluble arteannuin derivative is proven to have no toxic or side effects on normal cells.

Description

technical field [0001] The invention belongs to the field of chemical pharmaceutical engineering, and specifically relates to a water-soluble artemisinin derivative and its preparation and application. Background technique [0002] Artemisinin (artemisinin) is a new type of antimalarial drug extracted from Artemisia annua L. by Chinese scientists in 1971. It has the characteristics of high efficiency, quick action and low toxicity. It is the only one recognized by the World Health Organization in China. The botanical medicine researched and developed according to the research standard of western medicine is also the first traditional Chinese medicine product that is truly recognized globally. However, artemisinin's poor solubility and high recurrence rate limit its clinical application. Medicinal chemists began to do a lot of research on the structure modification and structure-activity relationship of artemisinin, and screened out some drugs with better curative effect. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/18A61K31/352A61P35/00A61P37/06
Inventor 胡宗利任彦荣陈国平
Owner CHONGQING UNIV
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