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Scutellarin compounds and preparation method and application thereof

A technology of scutellarin and compounds, which is applied in the field of scutellarin compounds and their preparation, can solve the problems of low absolute bioavailability and poor water solubility of scutellarin, and achieve the effect of solving adverse reactions

Active Publication Date: 2016-06-29
GUANGZHOU HENOVCOM BIOSCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Based on this, the object of the present invention is to overcome the defects of poor water solubility and low absolute bioavailability of scutellarin in the prior art, and to provide a scutellarin compound, which is highly water-soluble scutellarin Derivative prodrugs that can be rapidly converted to scutellarin in blood or in vivo by intrinsic enzymes

Method used

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  • Scutellarin compounds and preparation method and application thereof
  • Scutellarin compounds and preparation method and application thereof
  • Scutellarin compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation of embodiment 1 scutellarin sodium phosphate

[0065] Follow the directions below:

[0066]

[0067] (1) Preparation of scutellarin methyl ester of formula 2

[0068] Take 100mL of methanol in a two-necked flask, protect it with nitrogen, cool to 0°C, add acetyl chloride (2mL, 2.8mmol), add scutellarin (Compound 1) (4.62g, 10mmol) in DMF 15mL after 30min, and stir for 15 minutes , slowly return to room temperature, a white solid gradually precipitated out, react at 40°C for 4h, cool at -10°C for 1h, filter, wash the filtrate once with water, and dry the filter cake in vacuum. 3.65 g of yellow solid scutellarin methyl ester (shown in Formula 2) was obtained, with a yield of 77%. Product Characterization Data: 1 HNMR(400MHz,DMSO)δ10.37(s,1H,Ar-OH),8.61(s,1H,Ar-OH),7.94,7.92(d,2H,C 2’,6’ -H),6.99(s,1H,Ar-H),6.95-6.93(d,2H,C 3’,5’ -H),6.81(s,1H,C 8 -H),5.53-5.25(m,5H,Glu-H),4.18(s,3H,OMe).

[0069] (2) the preparation of the whole acetyl scutellari...

Embodiment 2

[0078] The preparation of embodiment 2 scutellarin sodium sulfonate

[0079] Follow the directions below:

[0080]

[0081] (1) preparation of formula 7 compounds

[0082]Place 2.58g of partial acetyl scutellarin of formula 4 and 0.716g of pyridine sulfur trioxide in a dry 50mL single-necked round bottom flask, add 5mL of pyridine and 10mL of DMF under stirring at room temperature, the reaction solution becomes clear, and continue stirring for 24 hours. Evaporate pyridine, add an appropriate amount of water, neutralize the eluent with 2N NaOH solution (2 equivalents of NaOH) to pH 7, separate macroporous resin AB-8, collect by elution with pure water, and evaporate to dryness under reduced pressure to obtain a yellow powder 1.2 g of the solid is the compound of formula 7. Product Characterization Data: MS(ESI):m / z=681.0[M-1] - .

[0083] (2) preparation of scutellarin sodium sulfonate of formula 13'

[0084] Place the compound of formula 7 in a 100mL round bottom flask...

Embodiment 3

[0086] The preparation of embodiment 3 scutellarin sodium methoxyphosphate

[0087] Follow the directions below:

[0088]

[0089] (1) Preparation of formula 9' compound

[0090] Dissolve 1 g of partial acetyl scutellarin of formula 4 in THF, add potassium carbonate, chloromethoxy di-tert-butyl phosphate, after TLC traces the reaction is complete, evaporate THF, add appropriate amount of water, and extract three times with DCM , dichloromethane:methanol ratio of 13:1 was used for column chromatography to obtain 400mg of the compound of formula 9'. Product Characterization Data: MS(ESI):m / z=677.0[M-1] - .

[0091] (2) Preparation of scutellarin methoxyphosphoric acid of formula 10

[0092] 200 mg of the compound of formula 9' was dissolved in 5 mL of 5% TFA in DCM, stirred at room temperature for 1 h, and the solvent was removed by rotary evaporation to obtain 160 mg of scutellarin methoxyphosphate compound (shown in formula 10).

[0093] (3) preparation of scutellarin ...

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Abstract

The invention discloses scutellarin compounds and a preparation method and an application thereof, and belongs to the technical field of medicinal chemistry. The compounds have the structural characteristic represented by the formula I, and have the advantages of good water solubility and high bioavailability. Moreover, the scutellarin compounds can be rapidly converted into scutellarin by an intrinsic enzyme in blood or bodies, so the scutellarin compounds can be used as prodrugs and are used for treatment of cardiovascular and cerebrovascular diseases, and the drug efficacy is improved compared with that of direct administration of scutellarin.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a scutellarin compound and its preparation method and application. Background technique [0002] Scutellarin, also known as scutellarin, scutellarin, scutellaria, etc., is a flavonoid compound extracted from the Yi nationality medicine scutellaria breviscapus, and its molecular structure is: [0003] [0004] Scutellarin is mainly used clinically to treat cerebral thrombosis, cerebral infarction, paralysis after stroke, coronary heart disease, angina pectoris and other diseases, with definite curative effect. However, due to its poor solubility (0.056g / L), the absolute oral bioavailability is low, only 0.4±0.19%, seriously affecting the effect of its oral application. Ordinary injections and powder injections have a short half-life and are eliminated rapidly in the body. Therefore, the clinical application of scutellarin is limited to a certain extent. [0005] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00C07H1/02A61K31/7048A61P9/00A61P9/10A61P7/02
CPCY02P20/55
Inventor 张健存王坤顾自强张袁超刘燕李德耀
Owner GUANGZHOU HENOVCOM BIOSCI CO LTD
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