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Isoflavone derivative, preparation method and application thereof

A technology for compounds and solvates, applied in the field of isoflavone derivatives and their preparation, achieves the effects of broad market prospect and simple and efficient preparation method

Active Publication Date: 2017-04-05
四川省川科中医药产业发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is no clinically effective drug for the treatment of Coxsackie virus. Antiviral drugs such as ribavirin, interferon, nutritional preparations, traditional Chinese medicine Huangqi Shenmai injection and other symptomatic and conservative treatments are commonly used.

Method used

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  • Isoflavone derivative, preparation method and application thereof
  • Isoflavone derivative, preparation method and application thereof
  • Isoflavone derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of the compound 4',7-diethylaglycone-5'-sulfonate (MJJ-S) of the present invention

[0032]

[0033] 1. Extraction and separation of Sheganoside

[0034] Chuanshegan crude drug was dried at 60°C, crushed into coarse powder and passed through a 20-mesh sieve, placed in an extraction container, heated and refluxed with 95% ethanol to extract 3 times, each time 1 hour, and the amount of each solvent was 4 times that of the medicinal material ( v / w). Filtrate while hot, combine filtrate, 60 DEG C depressurize recovery solvent, obtain the syrup-like substance (brown yellow extract) of specific gravity 1.2g / mL (60 DEG C measure), its yield is 49~51% (w / w). Treat the above-mentioned extract with chloroform, recover the solvent, add 95% ethanol (1 / 5 of the medicinal material, v / w) to the residue, stir evenly, and filter with suction to obtain the crude shegan glycoside. Take the crude product of Sheganoside, add 95% ethanol and heat it under reflux ...

Embodiment 2

[0044] Example 2 Preparation of the compound 4′,7-diethylaglycone-5′-sulfonate (MJJ-S) of the present invention

[0045] ① Shegan aglycon + diethyl carbonate → 4′,7-diethylshegan aglycone

[0046]

[0047]Take 100g of aglycone, add 20g of NaOH, mix well, add 300mL of 95% ethanol to a 2-liter round bottom flask, heat and boil in a water bath for 5 minutes, add 200mL of diethyl carbonate, react for half an hour, take it out, and use immediately Adjust the pH to 2-5 with hydrochloric acid, add water, stir and let cool. Filter to obtain a colorless powder, stir evenly with 95% ethanol, filter, wash repeatedly until the filtrate is nearly colorless, dry under reduced pressure at 60°C to obtain 100g of 4′,7-diethylsheganaglycone (light yellow crystalline powder, yield 70%). The sulfonation reaction is the same as in Example 1.

Embodiment 3

[0048] Example 3 Preparation of the compound 4′,7-diethylaglycone-5′-sulfonate (MJJ-S) of the present invention

[0049]

[0050]

[0051] Take Shegan aglycone 100g, iodoethane 100g, K 2 CO 3 100g was dissolved in 500mL DMF, and reacted for 6 hours at 60°C under the action of 40HZ ultrasonic waves. After the reaction was completed, the reactant was cooled to room temperature, and the insoluble matter was filtered off. The filtrate was distilled under reduced pressure to obtain a light yellow solid, which was recrystallized in chloroform to obtain 4′ , 7-diethyl shegan aglycone 100g (light yellow crystalline powder, yield 70%).

[0052] The sulfonation reaction is the same as in Example 1.

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PUM

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Abstract

The invention discloses an isoflavone derivative, which specifically is a compound shown as formula (I), or its solvate, or its pharmaceutically acceptable salt. Specifically, R1-R3 are independently selected from alkyl of C1-C6 respectively, and M represents alkali metal or hydrogen. Experiments prove that the compound provided by the invention has anti-Coxsachie virus effect in test mice, and has effects superior to those of control drugs under high, medium and low doses. Therefore, the compound provided by the invention can be used for preparation of anti-Coxsachie virus drugs, and has simple and efficient preparation method, thus having broad market prospects. (formula (I)).

Description

technical field [0001] The invention relates to an isoflavone derivative and its preparation method and application. Background technique [0002] Coxsackie virus is an enterovirus, divided into two types, type A and type B. After the virus enters the human body and reproduces in the pharynx and intestinal mucosal cells, it can invade the blood to form viremia, and then spread to the Central nervous system, respiratory tract, heart, muscle, skin, etc., can cause aseptic meningitis, rash fever, acute myocarditis and pericarditis, epidemic myalgia, upper flu, herpetic pharyngitis and infant diarrhea Wait. [0003] There is no clinically effective drug for the treatment of Coxsackievirus. Antiviral drugs such as ribavirin, interferon, nutritional preparations, traditional Chinese medicine Huangqi Shenmai injection and other symptomatic and conservative treatments are commonly used. [0004] Therefore, there is an urgent need for a better anti-Coxsackie virus drug in this fiel...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61P31/14
CPCC07D311/36
Inventor 袁崇均陈帅罗森王笳张磊李利民陈雏吴燕宁楠
Owner 四川省川科中医药产业发展有限公司
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