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A fluorescent probe based on pyrrole-coumarin dihydrazone derivatives and its preparation method and application

A fluorescent probe, coumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as nervous system disorders, and achieve high sensitivity, easy availability of raw materials, and highly selective fluorescence recognition performance Effect

Inactive Publication Date: 2020-04-07
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, high concentrations of copper can cause diseases such as nervous system disorders

Method used

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  • A fluorescent probe based on pyrrole-coumarin dihydrazone derivatives and its preparation method and application
  • A fluorescent probe based on pyrrole-coumarin dihydrazone derivatives and its preparation method and application
  • A fluorescent probe based on pyrrole-coumarin dihydrazone derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of pyrrole-coumarin dihydrazone derivatives

[0026]

[0027] Dissolve 195mg of 3,5-dimethylpyrrole-2-carbaldehyde in 10mL of absolute ethanol, then add 218mg of 4-hydroxy-3-acetylcoumarin hydrazone, and drop in 2 drops of glacial acetic acid, reflux and stir for 3h under normal pressure After cooling to room temperature, a large amount of solids were precipitated, filtered under reduced pressure, and the filter residue was washed with absolute ethanol to obtain a yellow solid, which was the target product, and the yield of the target product was 68%.

[0028] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the pyrrole-coumarin dihydrazone derivative that makes, the result is as follows:

[0029] 1 H NMR (400MHz, DMSO-d 6 ), δ (ppm): 16.36 (s, 1H, OH), 11.22 (s, 1H, NH), 8.41 (s, 1H, CH=N), 7.96-7.98 (d, 1H, Aryl-H), 7.62 -7.66(t,1H,Aryl-H),7.27-7.34(q,1H,Aryl-H),5.83(s,1H,CH),2.93(s,3H,CH 3 ),2.19(s,3H,CH...

Embodiment 2

[0032] Dissolve 390mg of 3,5-dimethylpyrrole-2-carbaldehyde in 20mL of 95% ethanol, then add 436mg of 4-hydroxy-3-acetylcoumarin hydrazone, drop in 2 drops of glacial acetic acid, reflux under normal pressure for 3h, cool After reaching room temperature, a large amount of solid was precipitated, filtered under reduced pressure, and the filter residue was washed with 95% ethanol to obtain a yellow solid, which was the target product, and the yield of the target product was 72%.

Embodiment 3

[0034] Dissolve 195mg of 3,5-dimethylpyrrole-2-carbaldehyde in 10mL of 75% ethanol, then add 218mg of 4-hydroxy-3-acetylcoumarin hydrazone, drop in 2 drops of glacial acetic acid, reflux under normal pressure for 3h, cool After reaching room temperature, a large amount of solid was precipitated, filtered under reduced pressure, and the filter residue was washed with 75% ethanol to obtain a yellow solid, which was the target product, and the yield of the target product was 78%.

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Abstract

The invention provides a fluorescent probe based on pyrrole-cumarin dihydrazone derivatives as well as a preparation method and application of the fluorescent probe. The chemical structural formula of the pyrrole-cumarin dihydrazone derivatives is shown in the description. The fluorescent probe based on the pyrrole-cumarin dihydrazone derivatives is prepared by using condensation reaction; the fluorescent probe is simple to synthesize and easy for obtaining raw materials; the fluorescent probe shows higher selective fluorescence identification performance for copper ions in multiple common metal ions, thus enabling the fluorescence of a solution containing the copper ions to be significantly quenched. More importantly, the fluorescent probe also can be used for biological tissues for detecting the fluorescence imaging of the copper ions in cellular microenvironment; the fluorescent probe has the characteristics of being rapid, simple and convenient and high in sensitivity and selectivity as well as wide potential application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a pyrrole-coumarin dihydrazone derivative and a preparation method and application thereof. Background technique [0002] Cu 2+ It plays an important role in biological systems of plants, humans and living cells. However, high concentrations of copper can cause diseases such as nervous system disorders. So far, fluorescence methods based on molecular chemical sensors have become the most important tools for the identification of metal ions because of their excellent properties such as simple operation and low detection limit. For Cu 2+ For the determination of ions, a large number of fluorescent probes have been reported. Therefore, Cu 2+ The study of fluorescent probes has potential practical value. Contents of the invention [0003] Usually pyrrole imine derivatives can form stable complexes with metal copper ions. In addition, coumarin derivatives have good...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07D405/12C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643G01N2021/6432
Inventor 王元吴伟娜李慧军闫玲玲吴浩
Owner HENAN POLYTECHNIC UNIV
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