Coumarin derivatives as well as preparation method and application thereof

A technology of coumarin derivatives and hydroxycoumarin, which is applied in biological testing, chemical instruments and methods, material inspection products, etc., can solve the problems of enhanced fluorescence intensity and no significant fluorescence response, and achieve the effect of enhanced fluorescence intensity

Inactive Publication Date: 2014-02-12
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, people have begun to pay attention to the design and synthesis of fluorescent probes with specific responses to cysteine, and synthesized several types of organic fluorescent probes, the representative ones are: coumarins, rhodamines, fluorescent Chrysin, fluorescent dye BODIPY, and naphthylhydrazone derivatives. After the probe compound reacts with cysteine, the fluorescence intensity is significantly enhanced, and some other common amino acids have almost no significant fluorescence response.

Method used

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  • Coumarin derivatives as well as preparation method and application thereof
  • Coumarin derivatives as well as preparation method and application thereof
  • Coumarin derivatives as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The preparation of embodiment 1 coumarin derivatives

[0025] (1) In a 100mL reaction flask, add 50mL of concentrated sulfuric acid, cool to 0°C with an ice-water bath, start stirring, add 5.5g (50mmol) resorcinol, and then dropwise add 6.8g (41.3mmol) 4-chloroacetyl Ethyl acetate, the rate of addition was controlled to keep the temperature of the reaction system at 0±2°C, and the reaction was stirred overnight at room temperature after the addition was complete. The reaction solution was poured into ice water, and a white solid was precipitated, filtered, washed with water, and dried to obtain 6.9 g of 4-chloromethyl-7-hydroxycoumarin, with a yield of 79.4%.

[0026] (2) In a 2L reaction flask, add 6.9g (32.8mmol) of 4-chloromethyl-7-hydroxycoumarin and 900mL of water, heat to reflux for 36 hours, cool, and precipitate a white solid, filter, wash with water, After drying, 5.9 g of 4-hydroxymethyl-7-hydroxycoumarin was obtained, with a yield of 93.7%.

[0027] (3) In ...

Embodiment 2

[0033] The preparation of embodiment 2 coumarin derivatives

[0034] (1) Same as embodiment 1;

[0035] (2) Same as embodiment 1;

[0036] (3) Same as embodiment 1;

[0037] (4) In a 10mL reaction flask, add 2mL water and 0.38g (2mmol) 7-hydroxycoumarin-4-carbaldehyde, start stirring, then add 0.198g (3mmol) malononitrile and 32μL 1-methylimidazole, The reaction was stirred at room temperature for 12 hours. Filter, wash with water, and dry to obtain 0.368g of 2,2-dicyano-3-(7-hydroxy-4-coumarinyl)oxirane, with a yield of 72.6%.

Embodiment 3

[0038] The preparation of embodiment 3 coumarin derivatives

[0039] (1) Same as embodiment 1;

[0040] (2) Same as embodiment 1;

[0041] (3) Same as embodiment 1;

[0042] (4) In a 10mL reaction flask, add 2mL water and 0.38g (2mmol) 7-hydroxycoumarin-4-carbaldehyde, start stirring, then add 0.264g (4mmol) malononitrile and 48μL 1-methylimidazole, The reaction was stirred at room temperature for 12 hours. Filter, wash with water, and dry to obtain 0.356g of 2,2-dicyano-3-(7-hydroxy-4-coumarinyl)oxirane, with a yield of 70.2%.

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Abstract

The invention provides coumarin derivatives as well as a preparation method and application thereof. The coumarin derivatives have the molecular formula: Cl3H6N2O4. The preparation method comprises the steps: firstly, preparing 4-chloromethyl-7-hydroxycoumarin, 4-hydroxymethyl-7-hydroxycoumarin and 7-hydroxycoumarin-4-formaldehyde; and then, adding the 7-hydroxycoumarin-4-formaldehyde into water, next, adding malononitrile and 1-methylimidazole, stirring at the room temperature, and filtering to obtain 2, 2-dicyano-3-(7-hydroxyl-4-coumarinyl)oxacyclopropane. The 2, 2-dicyano-3-(7-hydroxyl-4-coumarinyl)oxacyclopropane prepared by the preparation method can be used as a fluorescent probe for selectively detecting cysteine in an organism and can also be used for fluorescently marking cysteine in a cell so as to provide help for the diagnosis of related diseases in clinical medicals.

Description

technical field [0001] The present invention relates to a coumarin derivative, specifically a preparation method of 2,2-dicyano-3-(7-hydroxy-4-coumarinyl)oxirane and its use as a fluorescent probe in the detection of living organisms Cysteine ​​applications. Background technique [0002] Amino acid is the most basic substance that constitutes the protein of organisms and is related to life activities, and has a close relationship with the life activities of organisms. As one of the essential amino acids for the human body, cysteine ​​is one of the 20 amino acids involved in protein synthesis, and is also one of the three amino acids that build important glutathione; while homocysteine ​​is methyl sulfide It is an intermediate product of amino acid metabolism and does not participate in protein synthesis itself. The level of homocysteine ​​content in the body is associated with many diseases. Modern medical research shows that the expression of intracellular homocysteine ​​...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04C09K11/06G01N21/64G01N33/52
CPCC07D407/04C09K11/06C09K2211/1088G01N21/6402
Inventor 钞建宾张永斌张艳
Owner SHANXI UNIV
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