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Coumarin derivatives, preparation method of coumarin derivatives, and elastase activity detection method and kit

A technology of coumarin derivatives and elastase, which is applied in the application field of activity, can solve the problem of high-throughput screening of elastase inhibitors or accelerators, tedious high-performance liquid chromatography experiment process, storage and Harsh transportation conditions and other issues, to achieve the effect of low price, high atomic utilization rate, and high detection effectiveness

Active Publication Date: 2014-09-10
HUAZHONG NORMAL UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, the experimental process of high performance liquid chromatography is cumbersome, the cycle is long, and it is difficult to achieve high-throughput screening of elastase inhibitors or accelerators
The second is ultraviolet absorption spectrometry, which is simple to operate and fast in response, and has been widely used at present, but this method has the following two defects: First, the large background interference of ultraviolet absorption spectrometry leads to low sensitivity of analysis
The disadvantage of this method is that most of the peptide probes have poor stability under normal conditions, the storage and transportation conditions are harsh, and the atom utilization rate is low.
[0003] At present, there is no report on the use of non-peptide fluorescent probes for the detection of elastase activity and the screening of inhibitors or accelerators at home and abroad.

Method used

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  • Coumarin derivatives, preparation method of coumarin derivatives, and elastase activity detection method and kit
  • Coumarin derivatives, preparation method of coumarin derivatives, and elastase activity detection method and kit
  • Coumarin derivatives, preparation method of coumarin derivatives, and elastase activity detection method and kit

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preparation example Construction

[0026] The preparation method of the coumarin derivative of the present invention comprises: under the condition of nucleophilic reaction and the presence of an acid-binding agent, in an organic solvent, the compound represented by formula (2) is contacted with one of acid chloride or acid anhydride;

[0027] Formula (2)

[0028] Wherein, the acid chloride is selected from pentafluoropropionyl chloride, one of heptafluorobutyryl chloride, preferably, the acid chloride is pentafluoropropionyl chloride; the acid anhydride is selected from pentafluoropropionic anhydride, heptafluorobutyric anhydride One, preferably, the acid anhydride is pentafluoropropionic anhydride.

[0029] In the preparation method of the coumarin derivatives described in the present invention, the nucleophilic reaction is a reaction between the amino group and various substituted acid chlorides and acid anhydrides, and the conditions of the nucleophilic reaction include a temperature of minus 5 to 30°C, a...

Embodiment 1

[0071] This example is used to illustrate the preparation method of the coumarin derivatives of the present invention.

[0072] In an organic solvent (dichloromethane, 20ml), in the presence of an acid-binding agent (pyridine, 2.5mmol), the compound (7-amino-4-trifluoromethylcoumarin, 1mmol) represented by formula (2) ) and acid anhydride (pentafluoropropionic anhydride, 2 mmol) at 5° C. for 30 minutes to obtain a contacted material. Then the contacted material was washed with water (50ml) and saturated citric acid solution (50ml) in sequence to obtain the washed material. The oil phase in the washed material was separated and dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was purified by a silica gel column to obtain 0.15 g of a white solid product (1).

[0073] Detect this white solid product with NMR and MS, data is 1 H NMR (600MHz, DMSO-d 6 ): δppm: 7.03(s,1H), 7.79(s,2H), 7.88(s,1H), 11.82(s,1H)....

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Abstract

The invention provides coumarin derivatives. The coumarin derivatives are shown in the formula (1), and in the formula (1), R1 represents one of pentafluoroethyl and heptafluoropropyl and R2 represents one of trifluoromethyl, methyl, cyano group, pyridine ring and benzothiazole ring. The invention also provides a use of the coumarin derivatives in detection of elastase activity, and an elastase activity detection method and kit. The coumarin derivatives as fluorescent probes have high sensitivity, high enzyme affinity and high atom utilization rate in elastase activity detection. The coumarin derivatives are non-peptide fluorescent probes. Compared with the peptide fluorescent probes, the coumarin derivatives have higher stability, better use convenience and lower price.

Description

technical field [0001] The invention relates to a coumarin derivative, its preparation method and its application in detecting the activity of elastase. Background technique [0002] There are three main methods for measuring the activity of elastase (EC number: 3.4.21.37) in the prior art. The first is conventional high-performance liquid chromatography (HPLC), which can be directly used to detect neutrophil elastase-mediated hydrolysis of fibrinogen. However, the high-performance liquid chromatography experiment process is cumbersome, the period is long, and it is difficult to achieve high-throughput screening of elastase inhibitors or accelerators. The second is ultraviolet absorption spectrometry, which is simple to operate and fast in response, and has been widely used at present, but this method has the following two defects: first, the large background interference of ultraviolet absorption spectrometry leads to low sensitivity of analysis . Secondly, the substrate...

Claims

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Application Information

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IPC IPC(8): C07D311/18C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/6428
Inventor 杨光富杨文超李俊孙琦张春芳
Owner HUAZHONG NORMAL UNIV
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