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Methylquinolin-benzopyrylium derivative and preparation method and application thereof

A technology of benzopyrylium and methylquinoline, which is applied in the field of methylquinoline-benzopyrylium derivatives and their preparation, can solve the problems of poor sensitivity, application limitation, long response time, etc., and achieves enhanced Electrophilicity, achieve ultra-sensitive response, speed up effect

Active Publication Date: 2021-02-23
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A number of methods for the detection of SO have been reported 2 fluorescent probes, but they are sensitive to SO 2 The detection has defects such as long response time, poor sensitivity, nucleophilic interference ions have a great influence on its detection, and low fluorescence quantum yield. Or less organic solvents are introduced, which limits its application (Coordin. Chem. Rev., 2019, 388, 310; Free Radic. Biol. Med., 2019, 145, 42-60)

Method used

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  • Methylquinolin-benzopyrylium derivative and preparation method and application thereof
  • Methylquinolin-benzopyrylium derivative and preparation method and application thereof
  • Methylquinolin-benzopyrylium derivative and preparation method and application thereof

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Effect test

Embodiment 1

[0057] Embodiment 1 Synthesis of methylquinoline-benzopyrylium derivatives

[0058] (1) Synthesis of compound 1

[0059]

[0060] Put 3-diethylaminophenol (60.52 mmol, 10 g) and phthalic anhydride (60.52 mmol, 8.96 g) in a round bottom flask, add toluene (100 mL) under argon atmosphere, and reflux at 110 °C After reacting for 4 hours, cool the reaction mixture to 50-60°C, then add NaOH (50 mL) aqueous solution with a mass concentration of 35%, and react at 90°C for 6 hours. Acidified and placed at room temperature for 2 h, a precipitate precipitated out, filtered the precipitate, and recrystallized from ethanol to obtain a pale pink solid 2-(4-(diethylamino)-2-hydroxybenzoyl)benzoic acid (compound 1), the yield 89%.

[0061] (2) Synthesis of compound 2

[0062]

[0063] Compound (1 mmol, 313 mg) and 3-acetylquinoline (1 mmol, 171 mg) were dissolved in methanesulfonic acid (3 mL), reacted at 90 ° C for 9 h, the reaction system was cooled to room temperature, and Slowl...

Embodiment 2

[0070] Embodiment 2 CMQ is to SO in water phase system 2 selective detection of

[0071] Prepare CMQ with an initial concentration of 3 mM, prepare various anions and amino acids with an initial concentration of 30 mM, add 2.98 mL PBS and 10 μL CMQ to the fluorescence cuvette, and then add 10 μL sodium bisulfite (10 μM ), sodium sulfite (10 μM), sodium cyanide, sodium carbonate, sodium bicarbonate, sodium sulfate, sodium acetate, sodium nitrate, sodium chloride, sodium sulfide (10 μM), sodium sulfide (20 μM), sodium phosphate, bromine Sodium Chloride, Sodium Fluoride, Cysteine, Homocysteine, Glutathione, L-Serine, DL-Methionine, L-Phenylalanine, L-Lysine, L-Leucine, L-Proline, L-Histidine solution, SO only 2 Two forms of HSO exist in the aqueous system 3 - (sodium bisulfite) and SO 3 2- (Sodium sulfite) can significantly enhance the fluorescence intensity of CMQ at 640 nm, while other anions and amino acids cannot significantly change the fluorescence intensity of CMQ at...

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Abstract

The invention provides a methylquinolin-benzopyranium derivative and a preparation method and application thereof. The preparation method of the methylquinolin-benzopyranium derivative is simple, rawmaterials are cheap and easy to obtain, the synthesis cost is low, the methylquinolin-benzopyranium derivative shows the advantages of high selectivity, low detection limit, large Stokes shift and ultra-sensitive responsiveness to SO2 detection, and CMQ has good water solubility and can realize efficient detection of SO2 in a water phase system. Meanwhile, the CMQ has good biocompatibility, has agood fluorescence development effect in living cells, and can be used for detecting SO2 in the cells. The methylquinolin-benzopyranium derivative can also realize quantitative detection of SO2 additives in foods, can also be prepared into an SO2 detection kit, is convenient for determination of the content of SO2 additives in various foods, and has a wide market application prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and biosensing technology, and specifically relates to a methylquinoline-benzopyrylium derivative and a preparation method thereof, and also relates to the methylquinoline-benzopyrylium derivative It is used in the detection of sulfur dioxide in aqueous phase systems, food and living cell mitochondria. Background technique [0002] For a long time, sulfur dioxide (SO 2 ) is considered to be a toxic environmental pollutant, when the human body is acutely or chronically exposed to SO 2 increased risk of respiratory and cardiovascular disease, lung cancer, and many neurological disorders. At the same time, HSO 3 − / SO 3 2− It has good antibacterial, antibacterial and antioxidative properties, so it has been widely used as a preservative in food, wine and pharmaceutical processing industries. However, HSO 3 − / SO 3 2− Excessive ingestion of large amounts can cause asthma and other allergic ...

Claims

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Application Information

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IPC IPC(8): C07D405/04C09K11/06G01N21/64
CPCC07D405/04C09K11/06G01N21/6428G01N21/643G01N21/6486C09K2211/1029C09K2211/1088Y02A50/30
Inventor 包霞珍霍聪德袁勇
Owner NORTHWEST NORMAL UNIVERSITY
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