A kind of isoxazole derivative and its synthetic method and the application of detecting hydrogen sulfide

A synthesis method and derivative technology, applied in chemical instruments and methods, organic chemistry, measuring devices, etc., can solve problems such as long reaction time, achieve obvious detection signals, convenient operation, and shorten reaction time

Active Publication Date: 2020-04-17
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Then came a series of probes with nitro groups, for example linked to cyanine dyes and coumarins, but they all required long reaction times

Method used

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  • A kind of isoxazole derivative and its synthetic method and the application of detecting hydrogen sulfide
  • A kind of isoxazole derivative and its synthetic method and the application of detecting hydrogen sulfide
  • A kind of isoxazole derivative and its synthetic method and the application of detecting hydrogen sulfide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation and characterization of BDP-ZN1

[0037] 1) Stir anisaldehyde (6.0mmol, 0.84g) and 2,4-dimethylpyrrole (13.2mmol, 1.26g) in deoxymethylene chloride (250ml). Add 3 drops of trifluoroacetic acid and continue stirring at room temperature for 24 hours under the protection of argon. Dichlorodicyanobenzoquinone (6.0 mmol, 1.36 g) was then added and stirring was continued for 4 hours before triethylamine (15 mL) was added. Add BF after 30 minutes 3 ·Et 2 O (15mL), and the mixture was stirred at room temperature for 24 hours, and the mixture was concentrated and purified by silica gel column chromatography (ethyl acetate / dichloromethane / petroleum ether, 1 / 1 / 10, V / V, eluting) , to obtain the desired compound 1 as a dark red powder;

[0038] 2) Compound 1 (1mmol, 0.3g) and pre-prepared DMF / POCl 3 The mixture (6 mL / 6 mL, stirred in ice bath for 30 min) was dissolved in 1,2-dichloroethane, and the mixture was refluxed at 65° C. for 4 hr. Concentrated and purified ...

Embodiment 2

[0041] In the fluorescence cuvette, add 1800 μL PBS buffer solution, 200 μL DMSO, 1 μM BDP-ZN1 DMSO solution, gradually add hydrogen sulfide aqueous solution (0-280 μM), and measure the fluorescence intensity at 522 nm on a fluorescence spectrometer after 1 min after each addition. , the fluorescence intensity gradually increased (see Figure 4 ).

Embodiment 3

[0043] Prepare a PBS buffer solution with a pH of 7.4 and a concentration of 10 mM, prepare a 2 mM BDP-ZN1 solution with DMSO, and prepare a 2 mM hydrogen sulfide aqueous solution; in 8 cuvettes, take 1800 μL PBS buffer solution, 200 μL DMSO, and 1 μM BDP-ZN1 DMSO solution, the amount of hydrogen sulfide solution added was 35, 70, 105, 140, 175, 210, 245, 280μM, and after 1min, the fluorescence intensity at 522nm was measured on a fluorescence spectrometer as 205.9, 275.5, 353.8, 455.2, 539.2, 600.7, 635.9, 719.2, take the hydrogen sulfide concentration as the abscissa and the fluorescence intensity as the ordinate to draw a graph to obtain the working curve of the hydrogen sulfide concentration; the linear regression equation is: F-F 0 =2.14619c-137.4, the unit of c is 10 -6 mol / L (see Figure 5 ).

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Abstract

The invention provides an isoxazole derivative as well as a synthesis method and application thereof to detection of hydrogen sulfide. The Chinese name of the isoxazole derivative is (E)-5-(2-(5,5-difluoro-10-(4-methoxyphenyl)-1,3,7,9tetramethyl-5hydrodipyrrolo[1,3,2]diazaboro-2-yl)vinyl)-3-methyl-4-nitroisoxazole. The invention also provides a method for rapidly detecting the hydrogen sulfide; based on the isoxazole derivative, the method is used for quantitatively detecting the content of the hydrogen sulfide in a PBS (Phosphate Buffer Solution) (with the pH (Potential of Hydrogen) of 7.4) through a fluorescence spectrometer. By adopting the method, the hydrogen sulfide is rapidly and conveniently detected.

Description

technical field [0001] The invention relates to isoxazole derivatives, in particular to an isoxazole derivative and a synthesis method thereof, and the application of the derivative in rapid detection of hydrogen sulfide. Background technique [0002] For a long time, hydrogen sulfide has been considered as an odorous gas that is not friendly to the environment, and it is also considered to be very harmful to humans. However, when the existence of hydrogen sulfide was first discovered in the human brain in 1989, further experimental research showed that it is a signal molecule like NO and CO, and it is called the third gas signal molecule. Studies have shown that hydrogen sulfide, as an active sulfur species (RSS), plays an important role in the living body and affects the healthy growth of living bodies. As a signaling molecule, it can regulate vasodilation to maintain blood pressure, regulate cell growth and Apoptosis, regulation of inflammation, control of oxidative and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1055G01N21/6428G01N21/643
Inventor 霍方俊周娜阴彩霞
Owner SHANXI UNIV
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