Benzothiazole compound and preparation method thereof, and application as probe for hypobromous acid

A technology of benzothiazole and compounds, applied in the application fields of benzothiazole compounds and their preparation, and hypobromous acid probes, achieving the effect of short response time and increased conjugation degree

Active Publication Date: 2019-05-03
HUNAN CITY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no benzothiazole-based probes have been used to detect HBrO so far, so it is necessary to design and synthesize a benzothiazole-based probe to detect HBrO

Method used

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  • Benzothiazole compound and preparation method thereof, and application as probe for hypobromous acid
  • Benzothiazole compound and preparation method thereof, and application as probe for hypobromous acid
  • Benzothiazole compound and preparation method thereof, and application as probe for hypobromous acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthetic method of 3-bromoisatoic anhydride:

[0040] Bis(trichloromethyl)carbonate (1.039g, 3.5mmol) was added to a tetrahydrofuran solution of 2-amino-3-bromobenzoic acid (2.150g, 10mmol), and the resulting mixed solution was refluxed and stirred for 4h, then quenched by adding 20mL of water extinguished, filtered with suction, washed the filter cake with methanol, and dried in vacuo to obtain 1.754 g of the target product with a yield of 73%. 1 H NMR (400MHz, DMSO) δ11.10(s, 1H), 8.02(dd, J=8.0, 1.4Hz, 1H), 7.95(dd, J=7.8, 1.4Hz, 1H), 7.19(t, J= 7.9Hz, 1H). 13 C NMR (101MHz, DMSO) δ159.59, 146.99, 140.59, 139.94, 139.93, 129.06, 124.99, 113.34, 108.39.

[0041] The synthetic method of 2-benzothiazolyl-6-bromoaniline:

[0042] Under argon protection conditions, 3-bromoisatoic anhydride (2.226g, 9.2mmol) and 2-aminothiophenol (1.540g, 12.3mmol) and sodium acetate (0.615g, 7.5mmol) were dissolved in 80mL of acetic acid , The resulting mixed solution was heated ...

Embodiment 2

[0046] Synthesis of probes for benzothiazole compounds:

[0047] In a 50 mL round bottom flask, 2-benzothiazolyl-6-bromoaniline (2.7 mmol), 2-methylthiophenylboronic acid (3.3 mmol) and 1,1'-bis(diphenylphosphino)ferrocene Palladium(II) dichloride dichloromethane compound (0.15 mmol) was dissolved in 5 mL of toluene solution. Under argon protection, 2 mL of K was added to the mixture 2 CO 3 Solution (3.5M), reacted at 70°C for 24h. After TLC tracking detects that the reaction is complete, it is cooled to room temperature. After filtration and concentration under reduced pressure, it was purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:4) to obtain a light yellow solid-benzothiazole compound with a yield of 45%.

[0048] The synthetic method of 3-bromoisatoic anhydride and 2-benzothiazolyl-6-bromoaniline is the same as that of Example 1.

Embodiment 3

[0050] Synthesis of probes for benzothiazole compounds:

[0051] In a 50 mL round bottom flask, 2-benzothiazolyl-6-bromoaniline (3.3 mmol), 2-methylthiophenylboronic acid (3.9 mmol) and 1,1'-bis(diphenylphosphino)ferrocene Palladium(II) dichloride dichloromethane compound (0.15 mmol) was dissolved in 5 mL of toluene solution. Under argon protection, 2 mL of K was added to the mixture 2 CO 3 Solution (5M), reacted at 90°C for 24h. After TLC tracking detected that the reaction was complete, it was cooled to room temperature. After filtration and concentration under reduced pressure, it was purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:6) to obtain a light yellow solid-benzothiazole compound with a yield of 46%.

[0052] The synthetic method of 3-bromoisatoic anhydride and 2-benzothiazolyl-6-bromoaniline is the same as that of Example 1.

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Abstract

The invention provides a benzothiazole compound probe, which can be reacted with HBrO to generate a cyclo-sulfilimine bond, thus increasing the conjugation degree of the reaction system and making a red shift on the fluorescence intensity of the reaction system by 137 nm and a change on fluorescence intensity ratio by 234 times. The probe can selectively recognize the HBrO without interference byother active oxygen substances and metal ions. Besides, the probe has advantages of short responding time and high sensitivity for detecting the HBrO and can be used for measurement of content of theHBrO. In addition, by researching the influence of pH value on measurement of the HBrO by the fluorescent probe, the fluorescence intensity ratio (I580/I447) of a probe blank solution to a solution with addition of HBrO is hardly changed along with change of pH value in the range of pH 2.0-12.0, so that it is proved that the pH has no obvious influence on the fluorescence intensity ratio. Withoutaddition of HBrO to the probe, a cell has strong fluorescence of blue pathway and weak fluorescence of red pathway, and the fluorescence is hardly to be seen. After the HBrO is added, the cell has weakened fluorescence of the blue pathway and enhanced fluorescence of the red pathway.

Description

technical field [0001] The application belongs to the technical field of fluorescent probes, in particular to a benzothiazole compound and its preparation method and its application as a hypobromous acid probe. Background technique [0002] Bromine, which is the 28th element for the human body to maintain health, widely exists in animals, while hypobromous acid (HBrO) is produced in vivo by bromide (Br - ) and hydrogen peroxide (H2O2) are catalyzed by heme peroxidase such as myeloperoxidase (myeloperoxidase, MPO) or eosinophil peroxidase (eosinophilperoxidase, EPO), which are in type IV collagen Necessary factors for the formation of sulfilimine cross-linked scaffolds (Wu WJ, Chen Y H, D'Avignon A, et al. Biochemistry, 1999, 38(12): 3538-3548; Mccall A S, Cummings C F, Bhave G, et al. Cell, 2014, 157 (6): 1380-1392), wherein the type IV collagen cross-linked by sulfimide is an essential material (Fidler AL, Vanacore R M, Chetyrkin S V, etal. Proceedings of the National Aca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
Inventor 张劲彭天英张令君贺国文
Owner HUNAN CITY UNIV
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