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Coumarin thiocarbazone derivatives as well as preparation method and application thereof

A technology of coumarin thiocarbazone and derivatives, which is applied in chemical instruments and methods, instruments, analytical materials, etc., can solve the problems of few probes, limited number of ratiometric fluorescent probes, complex synthesis process, etc., and achieve The effect of strong selectivity, wide potential application value, and simple synthesis method

Inactive Publication Date: 2018-07-13
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the number of existing ratiometric fluorescent probes for zinc ions or copper ions is limited and the synthesis process is complicated, and there are very few probes that can simultaneously detect zinc ions and copper ions.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of Coumarin Thiocarbazone Derivatives

[0033]

[0034] Dissolve 2.59g of 3-acetyl-7-diethylaminocoumarin in 100mL of ethanol, then add 1.06g of thiocarbazide, reflux under normal pressure and stir for 2h, cool to room temperature, precipitate a large amount of solid, filter under reduced pressure, The filter residue was washed with ethanol to obtain a yellow solid, which was the target product, and the yield of the target product was 75%.

[0035] The prepared coumarin thiocarbazone derivatives were analyzed by nuclear magnetic resonance spectroscopy, and the results were as follows:

[0036] 1 H NMR (400MHz, d 6-DMSO)δ:10.27(1H,s,NH),9.64(1H,s,NH),8.42(1H) / 7.47-7.49(1H) / 6.75-6.77(1H) / 6.55(1H) for Ar-H ,4.94(2H,s,NH 2 ),3.43-3.49(4H,q,2CH 2 ),2.22(3H,s,CH 3 ),1.12-1.16(6H,t,2CH 3 ), see the specific NMR spectrum figure 1 ;

[0037] Mass Spectrum: ESI-MS: m / z=348.1433 for [M+H] + .Specific mass spectrogram see figure 2 .

Embodiment 2

[0039] Dissolve 5.18g of 3-acetyl-7-diethylaminocoumarin in 200mL of ethanol solution, then add 2.12g of thiocarbazide, reflux and stir for 4 hours under normal pressure, cool to room temperature, a large amount of solids are precipitated, and filter under reduced pressure , the filter residue was washed with ethanol to obtain a yellow solid, which was the target product, and the yield of the target product was 78%.

Embodiment 3

[0040] Example 3 Determination of Optical Properties of Coumarin Thiocarbazone Derivatives to Copper Ions and Zinc Ions

[0041] The coumarin thiocarbazone derivatives prepared in the above-mentioned embodiment 1 were used as fluorescent probes in DMF / H 2 In O(9 / 1,v / v) medium, the molar concentration is 5×10 -6 mol / L solution, respectively, at a molar concentration of 1×10 -5 mol / L Ag + , Al 3+ , Ca 2+ , Cd 2+ ,Co 2+ , Cr 3+ , Cu 2+ , Fe 3+ , Hg 2+ , K + , Mg 2+ ,Mn 2+ , Na + , Ni 2+ ,Pb 2 ,Zn 2+ Add an equal amount of the above-mentioned fluorescent probe solution in the solution of metal ions, and adopt a fluorescence spectrometer to carry out fluorescence spectrum analysis (excitation wavelength is 420nm) to it respectively, and the fluorescence spectrum diagram of gained is shown in image 3 . pass image 3 It can be seen that the coumarin thiocarbazone derivative prepared in Example 1 of the present invention is used as a fluorescent probe to interact w...

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Abstract

The invention relates to coumarin thiocarbazone derivatives as well as a preparation method and application thereof, belonging to the technical field of organic synthesis. The preparation method of the coumarin thiocarbazone derivatives comprises the following steps: S1, adding 3-acetyl-7-diethylamino coumarin into an organic solvent for dissolving, and then adding thiocarbazide to obtain a mixture; S2, enabling the mixture obtained in the S1 to be subjected to a reflux mixing reaction at the atmospheric pressure; S3, after the reaction is finished, cooling to the room temperature, separatingout solid, filtering under the reduced pressure, and taking filter residue; S4, washing the filter residue obtained in the S3 to obtain the coumarin thiocarbazone derivatives. The coumarin thiocarbazone derivatives have higher sensitivity and selectivity when being used as a fluorescent probe for detecting zinc ions and copper ions.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a coumarin thiocarbazone derivative and a preparation method and application thereof. Background technique [0002] Zinc and copper ions are widely distributed in cells and body fluids, and are directly involved in the growth and development of cells in vivo, reproduction, tissue repair, gene transcription, metalloenzyme catalysis, neurotransmission, immune function and other life metabolic processes. Studies have reported that zinc and copper ions are closely related to diseases such as Alzheimer's disease and epilepsy. In addition, zinc ions and copper ions also become important metal pollutants due to the large-scale mining and extensive use of zinc-copper ore. Scientists have been working on the detection of zinc and copper ions in biological and environmental systems using selective fluorescent sensing probes. [0003] In recent years, fluorescent molecular probe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/643
Inventor 王元吴伟娜李慧军吴浩王碗碗
Owner HENAN POLYTECHNIC UNIV
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