Coumarin-Tr * ger's base Fe < 3 + > fluorescent probe and preparation method thereof

A fluorescent probe, coumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve many problems such as

Active Publication Date: 2020-10-30
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of fluorescent probes have been designed and synthesized to identify Fe in the natural environment 3+ , but endogenous Fe in cells 3+ There are not many reports on the detection, imaging, and tracing of base(TB) is the Fe of the skeleton 3+ fluorescent probe

Method used

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  • Coumarin-Tr * ger's base Fe &lt; 3 + &gt; fluorescent probe and preparation method thereof
  • Coumarin-Tr * ger's base Fe &lt; 3 + &gt; fluorescent probe and preparation method thereof
  • Coumarin-Tr * ger's base Fe &lt; 3 + &gt; fluorescent probe and preparation method thereof

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Experimental program
Comparison scheme
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Embodiment

[0044] 1. Coumarin- Synthesis of base derivatives:

[0045] (1) Synthesis of compound 6, including:

[0046]

[0047] Intermediates 1-5 were synthesized with reference to literature methods. Dissolve Intermediate 5 (2.0mmol), Intermediate 3 (2.2mmol) and three drops of piperidine in absolute ethanol (15.0mL), reflux for 48h, cool to room temperature after the reaction, spin dry the solvent, and pass the crude product through a column Chromatographic purification (V Petroleum ether :V Ethyl acetate =3:1) Compound 6 (0.79 g, 69%) was obtained.

[0048] (2) Synthesis of compound 7:

[0049]

[0050] Intermediate 5 (2.0mmol), Intermediate 4 (2.2mmol) and three drops of piperidine were dissolved in ethanol (15.0mL) and heated to reflux for 48h. After the reaction, the mixture was cooled to room temperature and the solvent was spin-dried. The crude product was subjected to column chromatography. Purification (V Petroleum ether :V Ethyl acetate =3:1) Compound 7 (0.69 g, 66%) was obtai...

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Abstract

The invention discloses a coumarin-base Fe < 3 + > fluorescent probe which has a structural formula shown in the specification, and is prepared from multiple raw materials such as p-bromoaniline and paraformaldehyde through a multi-step reaction. The synthesis process has the advantages of mild reaction conditions, short reaction time and high yield. The coumarin-base Fe < 3 + > fluorescent probesolution emits green fluorescence and red fluorescence in a solid state, the fluorescence brightness is high, and all compounds have specific recognition capability on Fe < 3 + >, and are low in detection limit, quick in response and good in stability. Tests show that part of the product has a good inhibition effect on cancer cells.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a class of coumarin- base class Fe 3+ High-brightness fluorescent probe and its preparation method and application. Background technique [0002] As an essential trace element for the human body, iron is an essential component of hemoglobin and myoglobin, and participates in the transport and exchange of oxygen and carbon dioxide. But excessive iron can cause harm to the human body. Therefore, it is of great significance to establish a fast and efficient detection method. The current methods for detecting iron ions mainly include atomic absorption spectroscopy and high performance liquid chromatography. However, some methods are cumbersome to process, costly, and require large instruments and professional operations. Fluorescence spectroscopy has the advantages of fast response speed, low cost and high sensitivity, and is widely used in the identification of iron ions....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08C09K11/06A61K49/00G01N21/64
CPCC07D487/08C09K11/06A61K49/0039G01N21/6428C09K2211/1044C09K2211/1088G01N2021/6432G01N2021/6417
Inventor 吴翚陈雯苑睿张鹏宛瑜
Owner XUZHOU NORMAL UNIVERSITY
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