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5-site aromatic ring substituted diarylpyrimidine derivative as well as preparation method and application thereof

A technology of derivatives and substituents, applied in the fields of diarylpyrimidine derivatives and their preparation, derivatives and their preparation, can solve problems such as side effects and poor oral availability

Pending Publication Date: 2020-11-03
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the marketed drugs etravirine and rilpivirine, as typical representatives of the second-generation NNRTIs, have received extensive attention. However, due to the poor oral availability or side effects of these two drugs, further research is needed. Structural modifications to overcome the above problems

Method used

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  • 5-site aromatic ring substituted diarylpyrimidine derivative as well as preparation method and application thereof
  • 5-site aromatic ring substituted diarylpyrimidine derivative as well as preparation method and application thereof
  • 5-site aromatic ring substituted diarylpyrimidine derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Preparation of 4-((2-chloropyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile (IVB-2)

[0053] Weigh 2,4-dichloropyrimidine (IVB-1, 0.2g, 1.34mmol) and 4-hydroxy-3,5-dimethylbenzonitrile (0.16g, 1.07mmol) and dissolve in 20mL N,N-dimethyl In base formamide, add K 2 CO 3 (0.22g, 1.61mmol) and stirred overnight at room temperature. After the reaction, the above reaction solution was added dropwise to 150mL of water, a large amount of white solid was precipitated, filtered and dried in vacuum to obtain the intermediate IVB-2 with a yield of 86% and a melting point of 195-197°C.

Embodiment 2

[0054] Example 2: Preparation of 4-((2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile (IVB-3)

[0055] Weigh palladium acetate (0.11g, 0.5mmol) and 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.29g, 0.5mmol) into 15mL 1,4-dioxane , stirred at room temperature for 15 min. Then the above intermediate IVB-2 (3.12g, 10mmol) and cesium carbonate (4.89g, 15mmol) were added and stirred for another 10min. Finally, p-aminobenzonitrile (1.18g, 10mmol) was added, heated to 80°C for 6h under nitrogen protection, cooled and filtered, then concentrated, dissolved ethyl acetate (80mL), water (20mL×3), saturated saline (20mL) Washing in sequence, drying with anhydrous sodium sulfate, and silica gel column chromatography after filtration to obtain white solid IVB-3 with a yield of 50% and a melting point of 275-277°C.

Embodiment 3

[0056] Example 3: 4-((2-((4-cyanophenyl)amino)-5-iodopyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile (IVB-4) preparation

[0057] Weigh the above intermediate IVB-3 (0.94g, 3.3mmol) in a round bottom flask, add acetonitrile 20mL, add trifluoroacetic acid (1mL, 13.2mmol) and N-iodosuccinimide (0.97 g, 4.3mmol), continue stirring at room temperature. After the reaction, a white solid precipitated out. Filter and dry to obtain crude IVB-4. Yield: 97%, melting point: 283-285°C.

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Abstract

The invention provides a diarylpyrimidine derivative substituted by a 5-site aromatic ring. The diarylpyrimidine derivative has a structure as shown in a general formula I which is described in the specification. The invention also relates to a preparation method of the derivative and application of the derivative as an HIV inhibitor in preparation of anti-AIDS drugs.

Description

technical field [0001] The invention relates to a derivative and its preparation method and application, in particular to a 5-position aromatic ring substituted diarylpyrimidine derivative and its preparation method and application, belonging to the technical field of medicine. Background technique [0002] AIDS, also known as acquired immunodeficiency syndrome (Acquired immunodeficiency syndrome, AIDS), is an infectious disease mainly caused by the pathogen of AIDS, human immunodeficiency virus (Human immunodeficiency virus, HIV), mainly T cell immune function deficiency . Since its discovery in the 1980s, AIDS has become one of the major infectious diseases that seriously endanger human health. At present, the most commonly used clinical method for preventing and treating AIDS is highly active antiretroviral therapy (Highly Active Antiretroviral Therapy, HAART). Although the implementation of this therapy has greatly improved the suppression efficiency of HIV virus, but b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47C07D401/04C07D409/04C07D405/04A61P31/18
CPCA61K31/505A61K31/506A61P31/18C07D239/47C07D401/04C07D405/04C07D409/04
Inventor 刘新泳高萍展鹏宋淑
Owner SHANDONG UNIV
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