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Bifunctional complexing agent containing tetraphenyl ethylene as well as preparation method and application of bifunctional complexing agent

A tetraphenylethylene, bifunctional technology, applied in the field of organic bifunctional complexing agent synthesis, can solve the problems of affecting target binding and heavy synthesis workload, and achieve the effect of simple synthesis conditions, easy operation, and mild reaction conditions

Active Publication Date: 2019-03-08
CAPITAL UNIVERSITY OF MEDICAL SCIENCES +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reported dual-modal imaging of PET and fluorescence provides accurate information for the diagnosis of diseases, but they are all obtained by combining the PET part and the fluorescent part, which has the disadvantages of heavy synthetic workload and affecting the combination with the target.
A complexing agent with fluorescence and complexation has not been reported yet

Method used

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  • Bifunctional complexing agent containing tetraphenyl ethylene as well as preparation method and application of bifunctional complexing agent
  • Bifunctional complexing agent containing tetraphenyl ethylene as well as preparation method and application of bifunctional complexing agent
  • Bifunctional complexing agent containing tetraphenyl ethylene as well as preparation method and application of bifunctional complexing agent

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Experimental program
Comparison scheme
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preparation example Construction

[0042] The synthetic method of above-mentioned bifunctional complexing agent containing tetraphenylethylene specifically comprises the steps:

[0043] 1)

[0044] Under anhydrous conditions, dissolve an equimolar amount of o-hydroxybenzoyl tetraphenylethylene derivatives or o-hydroxybenzoyl derivatives in dichloromethane, chloroform or methanol, and add half the mole of the initial aldehyde group The amount of ethylenediamine, and then react at 0-80°C for 3-12h;

[0045] 2) Reduction of Schiff base

[0046] Add solvent ethanol or methanol or tetrahydrofuran to the product obtained in step 1), then add a reducing agent twice the molar amount of the initial raw material, and react for 10 minutes;

[0047] 3) Purification of imines

[0048] Use dilute hydrochloric acid with a concentration of 1-3mol / L as a neutralizing agent for neutralization, then add ethyl acetate for extraction, dry over anhydrous sodium sulfate, remove the solvent with a vacuum rotary evaporator, and perf...

Embodiment 1

[0054] 2,2'-(Ethane-1,2-diylbis((2-hydroxy-5-(1,2,2-triphenylethenyl)benzyl)azadiyl))diacetic acid

[0055] structural formula

[0056]

[0057] Reaction formula

[0058]

[0059] Synthesis of raw materials:

[0060] 2-Hydroxy-5-(1,2,2-triphenylvinyl)benzaldehyde, the structural formula is as follows:

[0061]

[0062] References 2017 Tetrahedron Letters, 58(20), 1980-1984;

[0063] 2,2'-((ethane-1,2-diylbis(azanediyl))bis(methylene))bis(4-(1,2,2-triphenylethenyl)phenol) , the structural formula is as follows:

[0064]

[0065] Reaction formula:

[0066]

[0067] A solution of 2-hydroxy-5-(1,2,2-triphenylethenyl)benzaldehyde (0.69 g, 2 mmol) was added to 20 ml of methanol at room temperature, and ethane-1,2-diamine ( 60 mg, 1 mmol). The solution was kept at room temperature at 60°C for 3 hours. NaBH at 0°C 4 (0.14g, 4mmol) was added to the solution in batches and reacted for 10 minutes. The reaction was then acidified to pH = 7 with 1M HCl while coolin...

Embodiment 2

[0078] 2,2'-tert-butyl-(ethane-1,2-diylbis((2-hydroxy-5-(1,2,2-triphenylethenyl)benzyl)azadiyl)) Diglutaric acid, the structural formula is as follows:

[0079]

[0080] Reaction intermediate: 2,2'-(ethane-1,2-diylbis((2-hydroxy-5-(1,2,2-triphenylethenyl)benzyl)azadiyl)di Dimethyl acetate

[0081] The structural formula is as follows:

[0082]

[0083] The reaction formula is as follows:

[0084]

[0085] The compound 2,2'-((ethane-1,2-diylbis(azanediyl))bis(methylene))bis(4-(1,2,2-triphenylethenyl) Phenol) (0.4g, 0.51mmol) and K 2 CO 3 (0.28g, 2mmol) solution was added in 45mL acetonitrile, stirred at room temperature for 0.5 hours, 1-(tert-butyl) 5-methyl 2-bromoglutaric acid ester (280mg, 1mmol) was added, and then reacted at 60 Stir overnight at °C. The reaction was filtered and evaporated in vacuo, purified with flash purifier (hexane / ethyl acetate=4 / 1) to give 2,2'-(ethane-1,2-diylbis((2-hydroxy-5- Dimethyl (1,2,2-triphenylethenyl)benzyl)azadiyl)diacetat...

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Abstract

The invention relates to a bifunctional complexing agent containing tetraphenyl ethylene as well as a preparation method and an application of the bifunctional complexing agent. The bifunctional complexing agent capable of realizing complexing with radioactive nuclide such as <68>Ga<3+> and the like is obtained by modifying tetraphenyl ethylene structure, so that the bifunctional complexing agenthas the fluorescence and PET (positron emission tomography) double-imaging function, and can realize targeted diagnosis of different types of diseases by combination with different targeting molecules. The bifunctional complexing agent is expected to be widely applied to research and development of new drugs. The bifunctional complexing agent has the advantages as follows: a), the bifunctional complexing agent not only has fluorescent property, but also can realize complexing with <68>Ga<3+>; b), mark conditions of <68>Ga<3+> are mild, and yield is high; c), by combination with different targeting molecules, a series of disease diagnosis drugs with the fluorescence and PET double-imaging function can be developed; d), the bifunctional complexing agent can also be applied to rapid detectionof metal ions such as Fe<3+>, Cu<2+> and the like.

Description

technical field [0001] The present invention relates to a kind of complexing agent, particularly refer to a kind of organic complexing agent containing tetraphenylethylene and its preparation method and radioactive labeling 68 Ga 3+ The application in the invention belongs to the field of organic bifunctional complexing agent synthesis. Background technique [0002] Bifunctional group complexing agents can selectively complex different radioactive metal ions, and then can diagnose or treat different tumors, and affect the stability and pharmacokinetics of drugs in vivo. Therefore, the development of new functional complexing Reagents are one of the hotspots in the fields of drug development, ion extraction and detection. Tetraphenylethylene is an important class of materials for aggregation and luminescence, and has been applied to many fields such as ion recognition, liquid crystal materials and cell imaging. Multimodal imaging molecular imaging technology integrates the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/16C07C229/16C07C229/24C07D249/08C07C273/18C07C275/16C07J9/00C07D259/00C09K11/06G01N21/64
CPCC07C229/16C07C229/24C07C275/16C07D249/08C07D259/00C07J9/005C09K11/06G01N21/643
Inventor 吴泽辉吴仁博黄勇刘松
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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