Niacin salvia miltiorrhiza phenolic ester derivative, preparation method and application thereof

A technology of nicotinic acid salvia and phenolic ester, applied in the directions of drug combination, steroids, cardiovascular system diseases, etc., can solve the problems of unstable tanshinones, low bioavailability, limited application, etc., to improve bioavailability and its stability, inhibition of flushing and hepatotoxicity, and the effect of convenient administration

Inactive Publication Date: 2011-06-01
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In addition, naturally occurring tanshinone compounds themselves also have the following defects: 1) low bioavailability, which limits their clinical application; 2) the o-quinone or p-quinone structure contained in tanshinone compounds is their activity site, but this active site has caused the instability and failure of tanshinone drugs and other defects
[0007] In addition, naturally occurring tanshinone compounds themselves also have the following defects: 1) low bioavailability, which limits their clinical application; 2) the o-quinone or p-quinone structure contained in tanshinone compounds is their activity site, but this active site has caused the instability and failure of tanshinone drugs and other defects

Method used

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  • Niacin salvia miltiorrhiza phenolic ester derivative, preparation method and application thereof
  • Niacin salvia miltiorrhiza phenolic ester derivative, preparation method and application thereof
  • Niacin salvia miltiorrhiza phenolic ester derivative, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1, nicotinic acid salvianol ester compound P1 Synthesis.

[0038] Cryptotanshinone (0.30 g) was dissolved in ethyl acetate (50 ml), and palladium on carbon (5%, 15.0 mg) was added. The air in the reaction system was pumped out with a water pump, and hydrogen gas was introduced, and this was repeated three times, so that the air in the reaction system was completely discharged. Regulate the hydrogen pressure in the system to be 1 atmosphere. After stirring for 10 minutes, a solution of nicotinic anhydride (0.50 g) and DMAP (0.30 g) in ethyl acetate was added to the reaction mixture. Stirring was continued for 2 hours and filtered. The filtrate was washed with water (17 ml X 3), dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain the target compound P1. The eluent was a mixture of ethyl acetate and petroleum ether (1:1). compound P1 The structural formula and characterization a...

Embodiment 2

[0041] Embodiment 2, nicotinic acid salvianol ester compound P1 Synthesis.

[0042] The method is the same as in Example 1, except that Raney nickel (20.0 mg) is used instead of palladium carbon, and the target product is also obtained P1 .

Embodiment 3

[0043] Embodiment 3, nicotinic acid salvianol ester compound P1 Synthesis

[0044] The method is the same as in Example 1, except that platinum dioxide (6 mg) is used instead of palladium carbon, and after catalytic hydrogenation for 5 minutes, nicotinic anhydride solution is added for reaction, and the target product is also obtained P1 .

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Abstract

The invention relates to a niacin salvia miltiorrhiza phenolic ester derivative as shown in a formula I or a formula II, a preparation method and application thereof. The preparation method comprises the following steps of: dissolving a tanshinone-type compound in an organic solvent; hydrogenating under the catalysis of a transition metal for a certain time to obtain a salvia miltiorrhiza phenolic compound as a reduced intermediate of the tanshinone-type compound, wherein no separation and purification is needed to be carried out on the intermediate; reacting the intermediate with a niacin anhydride compound to obtain a target product of the niacin salvia miltiorrhiza phenolic ester derivative after separation and purification. In the compound, a niacin-type compound and the salvia miltiorrhiza phenolic compound are connected through ester bonds, the compound is decomposed into the niacin-type compound and the salvia miltiorrhiza phenolic compound through metabolism, and the salvia miltiorrhiza phenolic compound can be spontaneously transformed into the tanshinone-type compound and collaboratively develops bioactivity together with the niacin-type compound. Therefore, the niacin salvia miltiorrhiza phenolic ester compound is a kind of potential mutual prodrug for treating the cardiovascular disease.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to a prodrug nicotinic acid salvianol ester derivative used for preparing cardiovascular diseases and a preparation method thereof. Background technique [0002] Niacin is a drug that regulates dyslipidemia and has been used clinically for more than 50 years. The main clinical effects of niacin are: lowering total cholesterol, triglycerides and low-density lipoprotein, and increasing high-density lipoprotein, thereby exerting an anti-atherosclerotic effect. It is currently the most effective drug for increasing high-density lipoprotein one. However, long-term use of niacin is likely to cause the following toxic and side effects: 1) increase the concentration of prostaglandins in the patient's body, causing flushing in the patient; 2) increase the activity of transaminases in the patient's body, causing liver poisoning in the patient. [0003] Tanshinone compounds are a class of d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61P9/00
Inventor 安林坤张大立程曦古练权
Owner SUN YAT SEN UNIV
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