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Organic long-afterglow compound, and preparation method and application thereof

A compound and long afterglow technology, applied in organic chemistry, chemical instruments and methods, medical preparations containing active ingredients, etc., can solve the problems of short imaging time and complicated preparation process, and achieve low biological toxicity, long imaging time, Effect of Long Imaging Time

Active Publication Date: 2020-01-24
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the shortcomings of the above-mentioned prior art, the object of the present invention is to provide an organic long-lasting compound and its preparation method and application. The organic long-lasting compound disclosed in the present invention solves the problems of short imaging time and complicated preparation process , and has good biocompatibility, so it has a good application prospect in photodynamic therapy

Method used

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  • Organic long-afterglow compound, and preparation method and application thereof
  • Organic long-afterglow compound, and preparation method and application thereof
  • Organic long-afterglow compound, and preparation method and application thereof

Examples

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preparation example Construction

[0044] One, the preparation method of organic long afterglow compound

[0045]The first step: the general preparation method of 4-substituted ether compounds (1):

[0046]

[0047] Compound 4-substituent phenoxy group element phenols (1mmol) and compound 4-substituent halogen benzene (1~3mmol) were dissolved in N,N-dimethylformamide (10mL) solution, after adding sodium carbonate at 60 Stir at ~150°C for 8-12 hours. The formed compound was extracted with ethyl acetate and washed with saturated brine to obtain 4-substituted ether compound 1.

[0048]

[0049] The second step: the general preparation method of 4-heterofluorenes and phenazine substituent ethers (2):

[0050] Compound 1 (1 mmol), heterofluorene-type and phenazine-type substituent compounds (2-6 mmol) were dissolved in N,N-dimethylformamide (20 mL) solution, and stirred at 80-160° C. for 10-36 hours. The formed precipitate was separated by vacuum filtration, washed with saturated brine, and recrystallized i...

Embodiment 1

[0056] Embodiment 1: Synthesis of organic long afterglow compound 3

[0057] The first step: the general preparation method of 4-fluorophenyl ether (1):

[0058]

[0059] Compound 4-fluorophenol (2mmol) and compound 4-fluoroiodobenzene (6mmol) were dissolved in N,N-dimethylformamide (20mL) solution, added sodium carbonate and stirred at 150°C for 24h. The formed compound was extracted with ethyl acetate and washed with saturated brine to obtain compound 1a.

[0060]

[0061] The second step: the general preparation method of 4-carbazolylphenyl ether (2):

[0062] Compound 1a (2mmol) and carbazole (12mmol) were dissolved in N,N-dimethylformamide (30mL) solution and stirred at 1,60°C for 36h. The formed precipitate was separated by vacuum filtration, washed with saturated brine, and recrystallized in acetone to obtain compound 3, whose structural formula is as follows:

[0063]

[0064] The following are the data of the name, serial number, yield, melting point, colo...

Embodiment 2

[0066] Embodiment 2: Synthesis of organic long afterglow compound 4

[0067] The first step: the general preparation method of 4-fluorophenyl sulfide (1):

[0068]

[0069] Compound 4-fluorothiophenol (2mmol) and compound 4-fluoroiodobenzene (2mmol) were dissolved in N,N-dimethylformamide (20mL) solution, added sodium carbonate and stirred at 60°C for 8 hours. The formed compound was extracted with ethyl acetate and washed with saturated brine to obtain compound 1b.

[0070]

[0071] The second step: the general preparation method of 4-carbazolylphenyl sulfide (2):

[0072] Compound 1b (2mmol) and carbazole (4mmol) were dissolved in N,N-dimethylformamide (30mL) solution and stirred at 80°C for 10 hours. The formed precipitate was separated by vacuum filtration, washed with saturated brine, and recrystallized in acetone to obtain compound 4.

[0073]

[0074] The following is the name, serial number, yield, melting point, color, state of matter, NMR, mass spectromet...

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Abstract

The invention discloses an organic long-afterglow compound, and a preparation method and application thereof, and belongs to the technical field of photodynamic therapy. According to the invention, the long-afterglow compound with a brand-new structure is designed and synthesized on the basis of oxygen group elements. The long-afterglow compound has the following advantages: 1, the imaging time islong, and nanosecond-grade imaging of traditional fluorescent imaging agents is improved to millisecond-imaging of the organic long-afterglow material; 2, the oxygen group elements are introduced into the long-afterglow compound, so that the yield of triplet excitons of molecules is introduced, and generation of reactive oxygen is promoted; 3, the excitation range of the long-afterglow compound can be extended to visible light, and the long-afterglow compound can easily achieve a good therapeutic effect under visible light irradiation and has low biological toxicity; and 4, the long-afterglowcompound has good biocompatibility. According to the invention, experiments prove that the compound has obvious inhibitory activity on Gram-positive bacteria, and thus the compound has a potential for being used as a photosensitizer for effective photodynamic therapy.

Description

technical field [0001] The invention belongs to the technical field of photodynamic therapy, and in particular relates to an organic long-lasting compound and its preparation method and application. Background technique [0002] Bacteria threaten the health of humans and the survival of flora and fauna in the surrounding environment. Therefore, the application of antibacterial agents is of great significance. However, long-term repeated use of the same fungicide has resulted in strong resistance of pathogenic bacteria to many current fungicides. In addition, many countries have banned the use of some fungicides that have adverse effects on the environment, humans or ecology. Therefore, it is of great significance to research and develop new sterilization methods with high efficiency, low toxicity and environmental protection. [0003] Bio-optical imaging technology (Bio-imaging) refers to the method of using optical detection means combined with optical molecules to image...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06A61K41/00A61P31/04
CPCA61K41/0057A61P31/04C07D209/86C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029
Inventor 何刚许乐天周琨叱干东东
Owner XI AN JIAOTONG UNIV
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