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Preparation method for a series of acridine chemiluminescence agents

A chemiluminescence and acridine technology, applied in the direction of organic chemistry, can solve the problems of high price, complex preparation process, single acridine compound, etc., and achieve the effect of low cost and simple process

Active Publication Date: 2013-09-11
SHENZHEN MAXCHEMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the complex preparation process of acridinium esters and acridine sulfonamide derivatives, there are only a few suppliers in the world, which leads to their high prices and hinders their promotion in the application of chemiluminescence detection.
[0004] At present, there is no comprehensive patent literature on the synthesis of acridine series in China, and foreign literatures are mostly limited to the synthesis of a single acridine compound, and the method is seriously polluted, and it is even impossible to complete the synthesis of acridine series compounds according to the literature method

Method used

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  • Preparation method for a series of acridine chemiluminescence agents
  • Preparation method for a series of acridine chemiluminescence agents
  • Preparation method for a series of acridine chemiluminescence agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] R=H, the preparation of acridine sulfonamide Ⅰ:

[0033] The first step: preparation of compound 2. Put 1.03g (10mmol) of compound 1, namely 4-aminobutyric acid, in a round bottom burner, add 40mL of dichloromethane, stir magnetically, cool to 0°C, add 2.02g (20mmol) of triethylamine and p-toluenesulfonate in sequence Acyl chloride 2.10g (11mmol), kept at 0°C for 1h, adjusted the pH to 3 with 1mol / L hydrochloric acid after the reaction, then extracted the product twice with 200mL ethyl acetate, took the organic phase and added anhydrous sodium sulfate After drying, the solvent was removed under reduced pressure to obtain 2.19 g (8.50 mmol) of the product compound 2 with a yield of 85%.

[0034] The second step: the preparation of compound 3. Put 1.12g (5mmol) of 9-acridinecarboxylic acid in a round-bottomed flask, add 25mL of tetrahydrofuran to dissolve it, stir magnetically, cool to -10°C, add 0.61g (6mmol) of triethylamine and 0.54% ethyl chloroformate in sequence ...

Embodiment 2

[0039] R=OMe (this substituent is attached as figure 1 On the carbon of the 1 position marked above), the preparation of acridine sulfonamide Ⅱ:

[0040] The first step: preparation of compound 2. Put 1.03g (10mmol) of compound 1, namely 4-aminobutyric acid, in a round bottom burner, add 40mL of dichloromethane, stir magnetically, cool to 0°C, add 2.02g (20mmol) of triethylamine and p-toluenesulfonate in sequence Acyl chloride 2.10g (11mmol), kept at 0°C for 1h, adjusted the pH to 3 with 1mol / L hydrochloric acid after the reaction, then extracted the product twice with 200mL ethyl acetate, took the organic phase and added anhydrous sodium sulfate After drying, the solvent was removed under reduced pressure to obtain 2.19 g (8.50 mmol) of the product compound 2 with a yield of 85%.

[0041] The second step: the preparation of compound 3, put 1.27g (5mmol) of 1-methoxy-9-acridinecarboxylic acid in a round bottom flask, add 25mL tetrahydrofuran to dissolve it, stir magnetically...

Embodiment 3

[0046] R=OMe, (this substituent is attached as figure 1 On the carbon of the 2 position marked above), the preparation of acridine sulfonamide Ⅲ

[0047] The first step: preparation of compound 2. Put 1.03g (10mmol) of compound 1, namely 4-aminobutyric acid, in a round bottom burner, add 40mL of dichloromethane, stir magnetically, cool to 0°C, add 2.02g (20mmol) of triethylamine and p-toluenesulfonate in sequence Acyl chloride 2.10g (11mmol), kept at 0°C for 1h, adjusted the pH to 3 with 1mol / L hydrochloric acid after the reaction, then extracted the product twice with 200mL ethyl acetate, took the organic phase and added anhydrous sodium sulfate Drying, removal of solvent under reduced pressure gives product 2.19g (8.50mmol) of compound 2, and the yield is 85%;

[0048] The second step: the preparation of compound 3. Put 1.27g (5mmol) of 2-methoxy-9-acridinecarboxylic acid in a round-bottomed flask, add 25mL of tetrahydrofuran to dissolve it, stir it magnetically, cool to ...

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Abstract

The invention provides a preparation method for a series of acridine chemiluminescence agents. The preparation method comprises the following steps: 1, dissolving 4-aminobutyric acid in a first solvent, stirring, cooling, sequentially adding triethylamine and p-toluenesulfonyl chloride, and carrying out pressure reduction solvent removing to obtain a product (a compound 2); 2, placing 9-acridinecarboxylic acid in a round bottom flask, adding a second solvent to dissolve the 9-acridinecarboxylic acid, stirring, cooling, sequentially adding a third solvent, carrying out a reaction, filtering the obtained solid, collecting the filtrate to obtain a filtrate A, dissolving the compound 2 with the second solvent, cooling, slowly adding an inorganic alkali in batches, carrying out a reaction, slowly adding the filtrate A to the reaction system in a dropwise manner, heating the reaction system to a room temperature, and carrying out the reaction overnight; and 3, placing a compound 3 in a flask, adding 1,3-propanesultone, stirring, carrying out a heating reaction, cooling to a room temperature, washing, filtering, and collecting the solid to obtain a compound 4 crude product. With the method, characteristics of simple process, green environmental protection, and low cost are provided.

Description

technical field [0001] The invention relates to a series of preparation methods of acridine esters and acridine sulfonamide derivatives, in particular to a chemical synthesis and purification method for preparing high-purity acridine series compounds. Background technique [0002] Acridine esters and acridine sulfonamide derivatives are a class of chemical substances that can be used as chemiluminescent markers. Its application to chemiluminescence detection has many advantages. The main advantages are: ① low background luminescence, high signal-to-noise ratio; ② less interference factors for luminescence reaction; ③ fast and concentrated light release, high luminous efficiency, and high luminous intensity; ④ easy to bind with proteins and the photon yield does not decrease after the association; ⑤ Markers are stable. Therefore, it is a class of very effective and very good chemiluminescent markers. [0003] Due to the complicated preparation process of acridinium esters ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
Inventor 任琪宫磊张娟凤谈宇清
Owner SHENZHEN MAXCHEMTECH
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