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Tetrazine compound, method for preparing same and application of tetrazine compound

A compound, tetrazine technology, applied in the field of preparation of tetrazine compounds, can solve problems such as the limited structure of tetrazine derivatives, the application of tetrazine bio-orthogonal fluorescent probes, etc.

Active Publication Date: 2017-01-11
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a tetrazine compound, which solves the problem that the structure of tetrazine derivatives synthesized from existing tetrazine compounds is limited, and the prepared tetrazine bio-orthogonal fluorescent probe is only suitable for fluorescence in the visible light region. molecular problem

Method used

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  • Tetrazine compound, method for preparing same and application of tetrazine compound
  • Tetrazine compound, method for preparing same and application of tetrazine compound
  • Tetrazine compound, method for preparing same and application of tetrazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] In this example, R 1 is a methyl group, and R is a methyl group.

[0065] The preparation method of tetrazine compound comprises the following steps:

[0066] 1), in a 50mL round-bottomed flask, dissolve compound 1 (280mg, 2mmol) in dry dichloromethane (1mL), slowly add a solution of boron tribromide in dichloromethane (0.4M, 2mL) dropwise to react In the bottle, the reaction solution was in N 2 After reacting at -78–25°C for 3 h under protection, the reaction solution was poured into water, shaken to separate the liquid, washed with water, and the solvent was removed by rotary evaporation to obtain compound 2 (219 mg), yield: 87%;

[0067] The structural formula of compound 1 is: The structural formula of compound 2 is:

[0068] Wherein, the preparation process of compound 1 is:

[0069] In a 50 mL round bottom flask, CH 3 CN (acetonitrile) (410mg, 10mmol) and methoxyacetonitrile (213mg, 3mmol) were dissolved in dry dioxane (1mL), zinc trifluoromethanesulfonat...

Embodiment 2

[0079] This example is based on Example 1, and the preparation methods of Compound 1-Compound 4 are consistent.

[0080] Compared with embodiment 1: have following difference: used alkali is tBuOK.

[0081] Compound 4 prepared in this example is used to prepare tetrazine derivatives 1:

[0082] in N 2 Under protection, 0.2mmol of compound 4 was added to 0.16mmol of acetaldehyde in THF solution, 0.22mmol of tBuOK was added, and reacted at 25°C for 2h. Ether:ethyl acetate=2:1 The product was separated and purified, and then dried to obtain tetrazine derivative 1, yield: 35%.

Embodiment 3

[0084] This example is based on Example 1, and the preparation methods of Compound 1-Compound 4 are consistent.

[0085] Compared with embodiment 1: have following difference: used alkali is Cs 2 CO 3 .

[0086] Compound 4 prepared in this example is used to prepare tetrazine derivatives 1:

[0087] in N 2 Under protection, add 0.2mmol of compound 4 to 0.16mmol of acetaldehyde in THF solution, add 0.22mmol of Cs2 CO 3 , and reacted at 25° C. for 2 h. After the reaction, the excess solvent was removed in vacuum, and then the product was separated and purified by thin-layer chromatography (petroleum ether: ethyl acetate=2:1, and then dried to obtain tetrazine derivative 1 , Yield: 25%.

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Abstract

The invention discloses a tetrazine compound, a method for preparing the same and application of the tetrazine compound. The tetrazine compound is tetrazine phosphate ester. The tetrazine phosphate ester prepared by the aid of the method can be applied to preparing tetrazine derivatives, and the tetrazine derivatives with fluorescent groups can be used as biological orthogonal fluorescent probes. The tetrazine compound, the method and the application have the advantages that the tetrazine phosphate ester is used as an intermediate for preparing the tetrazine derivatives, accordingly, different varieties of tetrazine derivatives can be prepared from the tetrazine phosphate ester and can be applied to the biological orthogonal fluorescent probes with far infrared / near infrared emission wavelengths and long Stoke's shift, the prepared biological orthogonal fluorescent probes are high in specificity, low in background signal and sensitive and efficient in fluorescent activation, and the like.

Description

technical field [0001] The invention relates to the technical field of preparation of tetrazine compounds, in particular to tetrazine compounds and their preparation methods and applications. Background technique [0002] Tetrazine compounds and their derivatives have more physiological activities, such as anti-inflammatory, analgesic, anti-viral, anti-bacterial and anti-cancer. Among them, tetrazine derivatives containing fluorescent groups can be used as bioluminescent orthogonal probes. Tetrazine derivatives and corresponding bioorthogonal chemistry have the advantages of good biocompatibility, in vivo stability, and rapid response, and have been widely used. It is applied in important research fields such as chemical biology and pharmacy to explore the life process of cells and tissues from the molecular and subcellular structure levels. More importantly, the inherent physical and chemical properties of tetrazine compounds allow them to be designed as bioluminescent ort...

Claims

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Application Information

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IPC IPC(8): C07F9/6524C07D257/08C07D409/06C09K11/06
CPCY02P20/55C07F9/6524C07D257/08C07D409/06C09K11/06C09K2211/1074C09K2211/1092
Inventor 吴昊星游姣
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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