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Phenothiazine benzaldehyde derivative and preparation method thereof, and phenothiazine quinoline molecular fluorescent probe and preparation method and application thereof

A technology of phenothiazine quinoline and fluorescent probe, which is applied in the field of phenothiazine benzaldehyde derivatives and its preparation, can solve the problems of lack of fast, effective, low-cost detection methods for environmental pollutants and intracellular active oxides, etc. Achieve the effects of simple and easy preparation method, wide range of pH value and widening of pH application range

Inactive Publication Date: 2019-08-16
SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of phenothiazine benzaldehyde derivative and its preparation method, phenothiazine quinoline molecular fluorescent probe and its preparation method and application, thereby solving the lack of rapid, effective and low-cost environment in the prior art Problems with the detection method of pollutants and intracellular reactive oxygen species

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  • Phenothiazine benzaldehyde derivative and preparation method thereof, and phenothiazine quinoline molecular fluorescent probe and preparation method and application thereof
  • Phenothiazine benzaldehyde derivative and preparation method thereof, and phenothiazine quinoline molecular fluorescent probe and preparation method and application thereof
  • Phenothiazine benzaldehyde derivative and preparation method thereof, and phenothiazine quinoline molecular fluorescent probe and preparation method and application thereof

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Embodiment 1

[0034] Embodiment 1, the preparation of phenothiazine benzaldehyde derivative

[0035] Proceed as follows:

[0036]1) Compound 4-N,N-diethylamino-2-hydroxyl-benzaldehyde (387mg, 2mmol) and 10-(6-bromo-hexyl)-10H-phenothiazine (1.08g, 3mmol) were added to In 20 mL of anhydrous acetonitrile, add 53 mg of potassium iodide, then add 550 mg of ground potassium carbonate, stir evenly, and react under reflux for 24 hours in the dark;

[0037] 2) After cooling to room temperature, add potassium tetrafluoroborate to the above reaction solution and stir for 2 hours for anion exchange, distill the obtained crude product solution under reduced pressure and extract with dichloromethane, collect the organic phase, and dry with anhydrous sodium sulfate , and the organic phase was spin-dried and purified by column separation. The eluent is petroleum ether: ethyl acetate (4 / 1, v / v). The purified product was dried in a vacuum oven to obtain 806 mg of oily substance with a yield of 85%.

Embodiment 2

[0038] Embodiment 2, the preparation of phenothiazine quinoline derivatives

[0039] Proceed as follows:

[0040] 1) Mix 4-diethylamino-2-(6-phenothiazin-10-yl-hexyloxy)-benzaldehyde (224mg, 0.5mmol) obtained in the above-mentioned Example 2 with N-ethyl-2 - Add methylquinoline iodonium salt (150 mg, 0.5 mmol) into 10 mL of absolute ethanol, add 200 μL of hexahydropyridine, and heat to reflux reaction in the dark. to 22°C;

[0041] 2) Add 63mg (0.5mmol) potassium tetrafluoroborate (KBF 4 ) and stirred and reacted for 2 hours, after anion exchange, the crude product was obtained;

[0042] 3) The above reaction solution was filtered to remove inorganic salts, the liquid phase was evaporated under reduced pressure to remove the solvent and concentrated to 3 ml, the solid product was recrystallized with 5 ml of absolute ethanol, and after drying, 246 mg of yellow solid product was obtained, which was the prepared 1 -{2-[4-Diethylamino-2-(4-phenothiazine-hexyloxy)-phenyl]-vinyl...

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Abstract

The invention provides a phenothiazine benzaldehyde derivative and a preparation method thereof, and a phenothiazine quinoline molecular fluorescent probe and a preparation method and application thereof. The phenothiazine quinoline molecular fluorescent probe is 1-{2-[4-diethylamino-2-(4-phenothiazine-hexoxy)-phenyl]-vinyl}-N-methyl quinolinium salt. According to the phenothiazine quinoline molecular fluorescent probe provided by the invention, a semi-cyanine dye is used as a fluorescent signal reporting group, and the preparation method of the phenothiazine quinoline molecular fluorescent probe is simple and easy to implement and low in cost. The molecular fluorescent probe not only has fast response to hypochlorous acid radicals, high selectivity and high detection sensitivity, but alsocan be used for detecting environmental heavy metal ions. The method is simple and easy to popularize and apply, and an important basis is provided for the fluorescent probe to be used for detectingintracellular active oxides and detecting heavy metals in environmental pollutants.

Description

technical field [0001] The invention relates to the synthesis and detection method of molecular probes in fluorescence sensing and detection technology, in particular to a phenothiazine benzaldehyde derivative and a preparation method thereof, a phenothiazine quinoline molecular fluorescent probe, a preparation method and application thereof. Background technique [0002] With the improvement of living standards and the rapid development of industry, a large amount of heavy metals are discharged into water bodies, which has become one of the important causes of water body and soil pollution. Due to the stability of heavy metals, most of them are difficult to decompose and will continue to accumulate in the natural environment, destroying the ecosystem and eventually entering the human body through drinking water and food. Heavy metals such as copper, zinc, iron, and manganese are not essential elements for life activities. Once they enter the human body, they will cause a se...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22C07D417/12C09K11/06G01N21/64
CPCC07D279/22C07D417/12C09K11/06C09K2211/1007C09K2211/1029C09K2211/1037G01N21/6428G01N21/643
Inventor 梁丽娟班业伟孙一萌赵建龙
Owner SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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