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6,8-dimethylol chrysin and 6,8-dimethylol ether chrysin, method for preparing same and pharmaceutical use

A technology of dihydroxyl and chrysin, applied in the direction of drug combination, pharmaceutical formula, medical preparations containing active ingredients, etc., can solve the problem of weak effect, achieve low production cost, good anti-hypoxia effect, and good therapeutic effect Effect

Inactive Publication Date: 2008-11-19
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

They have fewer side effects in the body, but their effects are weaker

Method used

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  • 6,8-dimethylol chrysin and 6,8-dimethylol ether chrysin, method for preparing same and pharmaceutical use
  • 6,8-dimethylol chrysin and 6,8-dimethylol ether chrysin, method for preparing same and pharmaceutical use
  • 6,8-dimethylol chrysin and 6,8-dimethylol ether chrysin, method for preparing same and pharmaceutical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] In this example, chrysin, solid KOH equal in mass to chrysin, and methanol solvent 20 times the mass of chrysin were added to the reaction kettle, and chrysin was completely dissolved in the solvent under stirring, and then 37% formaldehyde aqueous solution was added , make chrysin and formaldehyde carry out chemical reaction, the molar ratio of chrysin and formaldehyde used is 1: 5, make the temperature of reaction liquid be 15 ℃ with temperature adjustment device, after reacting for 40 hours, add 10% HCl to acidify to pH = 4. Poured into 5 times the volume of the reaction solution in water, a pale yellow precipitate precipitated out, filtered to obtain the crude product of formula (1), and purified the crude product by recrystallization with methanol to obtain the pure product of formula (1) (yield 85%). Adopt the formula (1) prepared by the present embodiment, after testing, its physical and chemical properties are as follows:

[0053] Pale yellow needle-like crystal...

Embodiment 2

[0059] In this example, add chrysin, solid KOH of the same quality as chrysin, and methanol solvent with 15 times the mass of chrysin in the reaction kettle, and completely dissolve chrysin in the solvent under stirring, then add paraformaldehyde to make Chrysin and paraformaldehyde carry out chemical reaction, the molar ratio of chrysin and paraformaldehyde used is 1: 3, make the temperature of reaction solution be 50 ℃ with temperature regulating device, after reacting for 10 hours, add 5% HCl to acidify to pH = 5, poured into 7 times the volume of the reaction solution in water, a pale yellow precipitate precipitated out, and the other processes were the same as in Example 1.

Embodiment 3

[0061] In this example, add chrysin, solid KOH equal in mass to chrysin, and methanol solvent with 25 times the mass of chrysin in the reaction kettle, completely dissolve chrysin in the solvent under stirring, and then add 15% formaldehyde solution , make chrysin and formaldehyde carry out chemical reaction, the molar ratio of chrysin and formaldehyde used is 1: 9, make the temperature of reaction liquid be 5 ℃ with temperature regulating device, after reacting for 70 hours, add 15% HCl to acidify to pH = 3. Poured into 5 times the volume of the reaction solution in water, there was a pale yellow precipitate, and the other processes were the same as in Example 1.

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PUM

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Abstract

The invention provides a 6, 8-bis(hydroxymethyl) chrysin, 6, 8-bis(hydroxymethyl) ether chrysin and a method for preparing the same. A preparation process comprises the following steps that: 6, 8-bis(hydroxymethyl) chrysin is obtained by using chrysin as lead compound to react with formaldehyde and potassium hydroxide in methanol; then 6, 8-bis(hydroxymethyl) ether chrysin-5, 7-dihydroxy-6, 8-bis(methoxymethyl) flavone, 5, 7-dihydroxy-6, 8- bis(ethoxy methyl) flavone and 5, 7-dihydroxy-6, 8-bis(butoxy methyl) flavone are synthesized by using the 6, 8-bis(hydroxymethyl) chrysin as an intermediate to react with methanol, ethanol and butanol; a pure product of a compound of the invention can be obtained through recrystallization. The invention also provides a medicine and a composition for treating cardiovascular and cerebrovascular diseases, wherein the medicine and the composition contain the 6, 8-bis(hydroxymethyl) chrysin or 6, 8-bis(hydroxymethyl) ether chrysin with effective therapeutic dose, as well as acceptable vector in pharmacy.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to a heterocyclic compound containing a six-membered ring without hydrogenation, with an oxygen atom as the only ring heteroatom, and fused with other rings. Background technique [0002] Flavonoids are the active ingredients of many commonly used Chinese herbal medicines, and have a wide range of pharmacological activities, such as: anti-cardiocerebral ischemia, anti-arrhythmia, anti-free radicals, analgesia, liver protection, anti-virus, anti-tumor and other pharmacological effects. They have fewer side effects in the body, but their effects are weaker. Chrysin (Chrysin), also known as chrysin, widely exists in nature and has high biological activity. Vascular and other pharmacological effects. Since the 1980s, people have started research on the chemical synthesis of chrysin. In recent years, research hotspots have focused on the synthesis of chrysin ...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P9/00
Inventor 李发荣张尊听陈莉莉吴臻王喆之
Owner SHAANXI NORMAL UNIV
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