Biphenyl furocoumarin compound and preparation method and application thereof

A technology of furanocoumarins and compounds, which is applied in the field of biphenyl-type furanocoumarins and their preparation, can solve the problems of toxic and side effects of chemical medicines, and that the treatment of chemical medicines cannot meet expectations, and achieve cheap and easy-to-obtain reagents, The effect of mild reaction conditions and simple operation of the reaction process

Active Publication Date: 2014-07-02
豆黄金食品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the different degrees of toxic and side effects of chemical drugs themselves, hypertension drugs with different mechanisms of action have different shortcomings, which often make the chemical ...

Method used

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  • Biphenyl furocoumarin compound and preparation method and application thereof
  • Biphenyl furocoumarin compound and preparation method and application thereof
  • Biphenyl furocoumarin compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] R in the structural formula of embodiment 1 1 is a fluorine atom, n is 2, R 2 Be the compound of dimethylamino, prepare by the following steps:

[0047] 1) Xanthotoxin (1) is demethylated by boron tribromide to obtain the compound Xanthoxylin (2)

[0048] Take 4.32g (20.00mmol) prickly ash toxin in a 250ml eggplant-shaped bottle, add 73ml of anhydrous dichloromethane, stir to dissolve, put it in an ice bath under nitrogen protection, and stir for 10-15min; at the same time, add 6.88ml of three Boron bromide was dissolved in 73ml of anhydrous dichloromethane to prepare a 1mol / L boron tribromide-dichloromethane solution for use.

[0049] When the temperature inside the eggplant-shaped bottle is constant, place the prepared boron tribromide-dichloromethane solution in a constant pressure dropping funnel, slowly drop it into the eggplant-shaped bottle stirred in an ice bath, and finish the dripping within 30 minutes. After the drop, the ice bath was removed, and the reac...

Embodiment 2

[0062] R in the structural formula of embodiment 2 1 is trifluoromethyl, n is 2, R 2 Be the compound of dimethylamino, prepare by the following steps:

[0063] Steps 1), 2), and 3) are the same preparation steps as in Example 1; Step 4) 5-bromo-9-(2-(dimethylamino)ethoxy)-7H-furan[3,2-g ] Chromene-7-one reacts with 2-trifluoromethylphenylboronic acid in a suzuki reaction, specifically:

[0064] 0.5g of 5-bromo-9-(2-(dimethylamino)ethoxy)-7H-furo[3,2-g]chromene-7-one was placed in a 50ml round bottom flask, and 20ml of 1,4-di Oxyhexane and 5ml of water were dissolved, and 0.6g of sodium carbonate, 0.25g of 2-trifluoromethylphenylboronic acid, and 0.33g of tetrakistriphenylphosphine palladium were added thereto, and the mixture was refluxed for 2.5 hours under nitrogen protection. After the reaction was completed, it was poured into water, extracted several times with a small amount of chloroform, the organic phase was dried over anhydrous sodium sulfate, the solvent was evap...

Embodiment 3

[0068] R in the structural formula of embodiment 3 1 is a fluorine atom, n is 2, R 2 Be the compound of pyrrole, prepare by the following steps:

[0069] Step 1) is the same as in Example 1, that is, the preparation steps from the compound xanthotoxin (1) to the compound xanthoxylin (2) are the same; after that, the phenolic hydroxyl group and N-(2-chloroethyl)pyrrole hydrochloride generate ether reaction, specifically:

[0070] Dissolve 0.40g (2.00mmol) of compound (2) in 10ml of treated anhydrous N,N-dimethylformamide (DMF), add 1.10g (8.00mmol) of anhydrous potassium carbonate, stir at room temperature for 30min, and then Add 0.55g (3.00mmol) of N-(2-chloroethyl)pyrrole hydrochloride, and react in an oil bath at 80°C under temperature control for 30h under nitrogen protection. After the reaction was cooled to room temperature, the system was poured into ice water and allowed to stand until the ice melted. After a small amount of extraction with chloroform several times, ...

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Abstract

The invention discloses a biphenyl furocoumarin compound and a preparation method and an application thereof; the provided biphenyl furocoumarin compound is a new compound with vasodilating activity, which is obtained by modifying and optimizing the structure based on a natural product imperatorin, reserving the pharmacological activity, improving the physicochemical property and enhancing the druggability. The preparation method of the biphenyl furocoumarin compound provided by the invention has the advantages of easily-obtained material source, mild reaction conditions, simple operation in reaction process, and cheap and easily-obtained reagents. The prepared biphenyl furocoumarin compound is a ramification of the imperatorin and has the effect similar to the imperatorin; an in vitro vascular ring tension research shows that the biphenyl furocoumarin compound has a relaxant effect on the mesenteric microvessels of rats, so that the biphenyl furocoumarin compound can be applied to preparing antihypertensive drugs.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and relates to a biphenyl type furanocoumarin compound and a preparation method and application thereof. Background technique [0002] Hypertension is currently one of the major diseases that seriously affect human health and threaten human life. It is the most common cardiovascular disease and is closely related to myocardial infarction, stroke, coronary heart disease, heart failure, and renal failure. At present, the incidence of hypertension in the global population has exceeded 10%, and the number of hypertensive patients in my country has exceeded 100 million. [0003] According to reports, the incidence of hypertension is increasing with age, but with the social pressure, environmental factors, improvement of living conditions and changes in dietary structure in recent years, the age of onset of hypertension is becoming more and more biased. Low, over the age of 30 has become a key gro...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/37A61K31/4025A61K31/453A61P9/08A61P9/12
CPCC07D493/04
Inventor 贺浪冲贺怀贞王涛王程张杰周楠
Owner 豆黄金食品有限公司
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