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A kind of organic long afterglow compound and its preparation method and application

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 complex preparation process and short imaging time, and achieve simplified preparation process, low biological toxicity, The effect of low toxicity

Active Publication Date: 2021-04-20
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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  • A kind of organic long afterglow compound and its preparation method and application
  • A kind of organic long afterglow compound and its preparation method and application
  • A kind of organic long afterglow compound and its preparation method and application

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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 its preparation method and application, belonging to the technical field of photodynamic therapy. The present invention designs and synthesizes a class of organic long-lasting compounds with a new structure based on oxygen group elements, which has the following advantages: 1. The imaging time is long, improving from the nanosecond level imaging of traditional fluorescent imaging agents to the millisecond level of organic long afterglow materials Imaging; 2. The introduction of oxygen group elements into organic long-lasting compounds increases the yield of triplet excitons of molecules and promotes the generation of active oxygen; 3. Its excitation can be extended to visible light, and it is easy to achieve better under visible light irradiation. 4. Good biocompatibility. The present invention proves through experiments that the above compound has significant inhibitory activity on Gram-positive bacteria, and thus has the potential of being 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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Patent Type & Authority Patents(China)
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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