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Tetrazine compound and its preparation method and application

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

Active Publication Date: 2019-03-01
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 and its preparation method and application
  • Tetrazine compound and its preparation method and application
  • Tetrazine compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] In this embodiment, R 1 Is methyl and R is methyl.

[0065] The preparation method of tetrazine compounds includes the following steps:

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

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

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

[0069] In a 50mL round bottom flask, add CH 3 CN (acetonitrile) (410mg, 10mmol) and methoxyacetonitrile (213mg, 3mmol) were dissolved in dry dioxane (1mL), zinc triflate (108mg, 0.3mmol) was added and hydrazine was...

Embodiment 2

[0079] This example is based on Example 1, and the preparation methods of compound 1 to compound 4 are the same.

[0080] Compared with Example 1: It has the following difference: the base used is tBuOK.

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

[0082] In N 2 Under protection, 0.2 mmol of compound 4 was added to 0.16 mmol of acetaldehyde in THF solution, 0.22 mmol of tBuOK was added, and the reaction was carried out at 25°C for 2 hours. After the reaction, the excess solvent was removed in vacuo, and then thin layer chromatography (petroleum Ether: ethyl acetate=2:1 to separate and purify the product, and then dry to obtain tetrazine derivative 1, yield: 35%.

Embodiment 3

[0084] This example is based on Example 1, and the preparation methods of compound 1 to compound 4 are the same.

[0085] Compared with Example 1: It has the following difference: the base used is Cs 2 CO 3 .

[0086] The 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 Cs 2 CO 3 And react at 25℃ for 2h. After the reaction, the excess solvent is removed in vacuo, and the product is separated and purified by thin-layer chromatography (petroleum ether: ethyl acetate = 2:1), and then dried to obtain tetrazine derivatives 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 preparation methods and applications thereof. Background technique [0002] Tetraazine compounds and their derivatives have many physiological activities, such as anti-inflammatory, analgesic, antiviral, antibacterial and anticancer. Among them, tetrazine derivatives containing fluorescent groups can be used as biofluorescence orthogonal probes. Tetraazine derivatives and the corresponding bioorthogonal chemistry have the advantages of good biocompatibility, in vivo stability, and rapid reaction. It is used 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 level. More importantly, the inherent physical and chemical properties of tetrazine compounds allow it to be designed as bio-fluorescence orthogonal probes. The fluorescen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6524C07D257/08C07D409/06C09K11/06
CPCY02P20/55
Inventor 吴昊星游姣
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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