Derivative of acyl thiourea pyridine, method for preparing same and application thereof

A technology of acyl thiouracil and derivatives, which is applied in the field of acyl thiouracil derivatives and their preparation, and can solve the problems of affecting physiological activity and the like

Inactive Publication Date: 2011-04-27
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that substitutions at different positions on the pyrimidine ring will significantly affect its physiological activity

Method used

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  • Derivative of acyl thiourea pyridine, method for preparing same and application thereof
  • Derivative of acyl thiourea pyridine, method for preparing same and application thereof
  • Derivative of acyl thiourea pyridine, method for preparing same and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation of embodiment 1,2-amino-5-bromo-4-bromomethylpyrimidine (compound 2)

[0043] Put 1.09g (10mmol) of compound (1) in a 250mL round bottom flask, add 40mL glacial acetic acid to dissolve, add 0.256mL liquid bromine, and the solution is transparent yellow. Stir at room temperature and monitor by TLC. After the reaction, NaOH and Na 2 CO 3 The pH was adjusted to 7, and a large amount of solid precipitated out. Suction filtration, wash with a large amount of water, transfer the filter cake, and dry to obtain a white solid.

Embodiment 2

[0044] The preparation of embodiment 2,2-amino-5-bromo-4-bromomethylpyrimidine (compound 3)

[0045] Put 1.09g (10mmol) of compound (1) in a 250mL round-bottomed flask, add 40mL of glacial acetic acid to dissolve, add dropwise 0.76mL of liquid bromine, and the solution turns orange-red. After stirring at room temperature, the solution became cloudy after 15 minutes. Continue to stir, and when the solution turns from turbid to clear (about 1 h), quickly add 160 mL of distilled water to obtain a white powdery precipitate and a light yellow supernatant. Filter with suction, wash with a small amount of water, and transfer the filter cake. Methanol-dioxane was recrystallized and dried in vacuo to obtain a white solid.

Embodiment 3

[0046] Embodiment 3, the synthesis of N-[5-bromo-4-phenacylmethylpyrimidin-2-yl]benzoylthiourea

[0047] R 1 =Br

[0048] (1) Preparation of (2-amino-5-bromo-pyrimidin-4-ylmethyl) benzoate (8)

[0049]Add 31.00 g (3.7 mmol) of compound (3) and about 10 mL of DMF to a 100 mL Erlenmeyer flask, and then add 5 mL of an aqueous solution containing 1.60 g (11.1 mmol) of sodium benzoate. Ultrasonic reaction 4h. Add about 50 mL of distilled water, refrigerate and crystallize, filter with suction, wash, and dry in vacuo to obtain a milky white solid. Yield: 75.8%. m.p.130℃~135℃.

[0050] (2) Preparation of benzoyl isothiocyanate

[0051] Add 880mg (9mmol) of KSCN and about 15ml of freshly distilled anhydrous CH to a 100ml eggplant-shaped bottle 3 CN, slowly dropwise into anhydrous CH containing 0.84 mL of benzoyl chloride 3 CN about 10mL, reflux for 2h, and filter with suction. The filtrate was directly carried out to the next reaction without further processing.

[0052]...

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Abstract

The invention relates to a thiourea compound, a method for preparing the same and application thereof, in particular to a derivative of acyl thiourea pyridine, a method for preparing the same and application thereof. The method comprises the following steps: using 2-amino-4-methyl pyridine as a raw material to synthesize a derivative of the 2-amino-4 substituted pyridine; reacting acyl chloride and potassium thiocyanate to obtain a coarse product of acyl isothiocyanate, and reacting the coarse product and the pyridine derivative to obtain the corresponding acyl thiourea pyridine compound. Thederivative of the acyl thiourea pyridine prepared by the method has the actions of resisting the influenza virus activity, the hepatitis B virus activity and the oxidization and inhibiting the regeneration of vascular smooth muscles, so that the derivative of the acyl thiourea pyridine can be used for preparing medicaments of resisting the influenza virus activity, the hepatitis B virus activity and the oxidization and inhibiting the regeneration of the vascular smooth muscles.

Description

technical field [0001] The present invention relates to a thiourea compound and its preparation method and use, in particular to an acylthiouracil derivative and its preparation method and use. Background technique [0002] A large number of experiments have found that pyrimidine compounds are a class of compounds with important "dominant structures" and special effects. This type of compounds has become a hot spot for structure selection in the development of new drugs. Especially in recent years, the research and development of pyrimidine derivatives has attracted the attention of more and more scholars at home and abroad. Studies have shown that substitutions at different positions on the pyrimidine ring will significantly affect its physiological activity. It has been reported in the literature that 2,4-diaminopyrimidine derivatives have good protein tyrosine phosphatase 1B inhibitory activity; 2-amino-4-alkoxy substituted pyrimidine derivatives have biological activity...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42C07D401/12C07D405/12A61K31/505A61K31/506A61P31/16A61P31/20A61P39/06A61P9/00
Inventor 李青山田静班树荣
Owner SHANXI MEDICAL UNIV
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