Puerarin derivatives containing nitrate substituent groups and preparation method and medicinal application thereof

A technology of puerarin derivatives and substituents, which is applied in the field of chemical pharmaceuticals and can solve problems such as instability and failure

Inactive Publication Date: 2011-05-11
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the aqueous solution of nitric oxide is very difficult to prepare and very unstable, resulting in a large number of experiments all ended in failur

Method used

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  • Puerarin derivatives containing nitrate substituent groups and preparation method and medicinal application thereof
  • Puerarin derivatives containing nitrate substituent groups and preparation method and medicinal application thereof
  • Puerarin derivatives containing nitrate substituent groups and preparation method and medicinal application thereof

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Experimental program
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Embodiment Construction

[0061] The method for chemically synthesizing above-mentioned nitrate derivatives provided by the invention is shown in the following synthetic route:

[0062]

[0063] 1) Methylsulfonylation of the 6-position hydroxyl group of puerarin (P->Ms-P);

[0064] Dissolve 2.49g (6mmol) puerarin in 15ml pyridine, put it in a 100ml pear-shaped bottle, connect a 60ml constant pressure dropping funnel, and fill the funnel with 30ml pyridine and 0.71g (6.2mmol) methanesulfonyl chloride. The liquid was dripped under constant pressure at 0 degrees Celsius, and the dripping was completed for about 2 hours, and the stirring was continued overnight, and the temperature was gradually increased from 0 degrees Celsius to room temperature. The supernatant was diluted and developed by TLC (developing solvent: ethyl acetate: methanol: acetic acid = 20: 1: 0.5), the main product Rf = 0.4. After the mixture was filtered, the solvent was evaporated and then separated by column chromatography with m...

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Abstract

The invention discloses puerarin derivatives containing nitrate substituent groups (-ONO2). The puerarin nitrate derivatives are obtained with high yield by compact and efficient chemical reaction. The problems of poor water solubility and lipid solubility of puerarin and poor stability of NO donors are solved. The puerarin derivatives are flavone glycoside compound nitrate derivatives with synergism function, which are obtained by taking puerarin derivatives of a structural general formula I as parent compounds and substituting nitrate (-ONO2) substituent groups for one or more hydrogen atoms in the parent compounds. The puerarin derivatives have potential medicinal values on the aspect of treating heart and brain circulating diseases, central nervous system diseases and gastrointestinal system diseases.

Description

【Technical field】: [0001] The invention belongs to the technical field of chemical pharmacy. Specifically, it relates to a preparation method of a nitrate derivative of a flavonoid isoflavone glycoside compound and its medicinal use. Based on the natural active precursors of flavonoid isoflavone glycosides, the method utilizes chemical means and drug combination technology to prepare a kind of flavonoid isoflavone glycoside compound nitrate drug derivatives with synergistic function. Improve efficacy, reduce toxic and side effects, and provide a new way for the development of new traditional Chinese medicine flavonoid isoflavones. 【Background technique】: [0002] Research in the past ten years has shown that endogenous NO is an important vascular endothelial relaxing factor (endotheli-umderived relaxing factor, EDRF). EDRF acts on adjacent vascular smooth muscle, causing smooth muscle relaxation by increasing the level of intracellular cGMP. Vasodilation, hypertension and ...

Claims

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Application Information

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IPC IPC(8): C07D407/04A61K31/352A61P9/00A61P25/28A61P1/00
Inventor 王文君金辰李铁海郭丽娜赵炜王鹏
Owner NANKAI UNIV
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