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6-hydroxy genistein-5'-sulfonate as well as preparation method and application thereof

A technology of genistein and sulfonate, which is applied in the field of 6-hydroxygenistein-5'-sulfonate and its preparation, and can solve the problems such as no reports on 6-hydroxygenistein and its activity. , to improve the body's ability to tolerate hypoxia, a wide range of applications, and prolong the survival time.

Inactive Publication Date: 2017-12-01
SICHUAN ACAD OF CHINESE MEDICINE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There is no report on the salt of 6-hydroxygenistein and its activity

Method used

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  • 6-hydroxy genistein-5'-sulfonate as well as preparation method and application thereof
  • 6-hydroxy genistein-5'-sulfonate as well as preparation method and application thereof
  • 6-hydroxy genistein-5'-sulfonate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of 6-hydroxygenistein-5′-sodium sulfonate from 6-hydroxygenistein

[0033] Add 6-hydroxygenistein into the reaction kettle, then add 4 times the amount (ml / g) of sulfuric acid (V / W), the concentration is 85-98%, stir with a mixer until it is completely dissolved, and let it stand for 2 hours to react. Slowly pour into 40 times the amount (V / W) of saturated sodium chloride aqueous solution, stir while adding, a large amount of off-white precipitate precipitates, leave it overnight, filter, and obtain the crude product of 6-hydroxygenistein-5′-sodium sulfonate ; Recrystallize twice with water to obtain the refined product of 6-hydroxygenistein-5'-sodium sulfonate with a yield of 80%. This product is light yellow needle crystal or crystalline powder; odorless; easily soluble in hot water, soluble in water, insoluble in methanol and ethanol. UV lambda max 273n m; IR, 1 H NMR, 13 See CNMR, MS Figure 1~4 .

[0034] Reaction end point with silica g...

Embodiment 2

[0037] Example 2 Preparation of 6-hydroxygenistein-5′-sodium sulfonate from Shegan aglycon

[0038] Add Shegan aglycon into the reaction kettle, then add 4 times the amount (ml / g) of sulfuric acid (V / W), stir with a mixer until it is completely dissolved, leave it to react for 2 hours, and slowly pour the reaction solution into 40 times the amount (ml / g) g) in a saturated solution of sodium chloride, stirred while adding, a large amount of off-white precipitates precipitated, left overnight, filtered to obtain the crude product of sodium sulfonate-5'-sulfonate; recrystallized twice with water to obtain aglycone-5'- The refined product of 5'-sodium sulfonate (90% yield).

[0039] Add Shegan aglycone-5'-sodium sulfonate into the reaction kettle, then add 3 times the amount (ml / g) of water, stir with a mixer and heat to reflux, after the Shegan aglycone-5'-sodium sulfonate is completely dissolved, Then add 3 times the amount (ml / g) of hydroiodic acid (content ≥ 45%), stir, heat ...

Embodiment 3

[0042] Example 3 Preparation of 6-Hydroxygenistein-5′-Sodium Sulfonate from Puertinin

[0043] Add puerarin into the reaction kettle, then add 4 times the amount (ml / g) of sulfuric acid (V / W), stir with a mixer until it is completely dissolved, leave it to react for 2 hours, and slowly pour the reaction solution into 40 times the amount (ml / g) / g) in a saturated aqueous solution of sodium chloride, stirring while adding, a large amount of off-white precipitates precipitated, left overnight, filtered to obtain the crude product of puerarin-5'-sodium sulfonate; recrystallized twice with water to obtain kudzu flower Aglycon-5'-sodium sulfonate refined product (yield 90%).

[0044] Add puerarin-5'-sodium sulfonate into the reaction kettle, then add 3 times the amount (ml / g) of water, stir with a mixer and heat to reflux until the puereside-5'-sodium sulfonate is completely dissolved Finally, add 3 times the amount (ml / g) of hydroiodic acid (content ≥ 45%), stir, heat and reflux f...

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Abstract

The invention discloses a 6-hydroxy genistein-5'-sulfonate as well as a preparation method and application thereof. The 6-hydroxy genistein-5'-sulfonate is prepared from 6-hydroxy genistein, rhizome belamcandae chinensis aglycone and flos puerariae lobatae aglycone, has pharmacological activity, namely, obvious anti-hypoxia effect, can obviously prolong the survival time of mice with acute cerebral ischemia, significantly improves the hypoxia tolerance ability of the body, shows certain activity on HCT116, MCF-7, A549 cell strains and has significant protection effects on H2O2-induced PC12 cell injury. The 6-hydroxy genistein-5'-sulfonate is applied to drugs for treating cardiovascular and cerebrovascular diseases, vascular dementia and tumors, especially is prepared into preparations of injections, tablets, capsules, pills or oral solutions to extend the application range.

Description

technical field [0001] The invention relates to 6-hydroxygenistein-5'-sulfonate and its preparation method and application, belonging to the field of medicinal chemistry. Background technique [0002] 6-Hydroxygenistein, molecular formula C 15 h 10 o 6 , the chemical name is 5,6,7,4'-tetrahydroxyisoflavone or 5,6,7-trihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, Its structural formula is [0003] [0004] There are few studies on 6-hydroxygenistein. At present, it is mainly considered to be a bacterial metabolite, which is mainly obtained by isolating from bacterial metabolites. Currently, only 6-hydroxygenistein has hepatoprotective activity, and no other activity or efficacy has been reported on its pharmacological activity. [0005] There is no report on the salt of 6-hydroxygenistein and its activity. Contents of the invention [0006] The object of the present invention is to provide a kind of 6-hydroxygenistein-5'-sulfonate and its preparation method a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/352A61P9/00A61P25/00A61P25/28A61P35/00
CPCC07D311/36
Inventor 袁崇均陈帅罗森陈雏王笳谭正怀罗霞余梦瑶熊静悦
Owner SICHUAN ACAD OF CHINESE MEDICINE SCI
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