Compound, and its preparing method and use

A compound, alkyl technology, applied in the field of small molecule organic compounds

Inactive Publication Date: 2007-06-13
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no invention of AMPK activators, and the currently used AICAR is only a non-specific AMPK activator. Therefore, research and deve

Method used

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  • Compound, and its preparing method and use
  • Compound, and its preparing method and use
  • Compound, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the preparation of compound 5a

[0044] [Chemical Reaction Formula 4]

[0045]

[0046] According to the above chemical reaction formula:

[0047] Step 1: Add 28mg of AlLiH to a 25ml round bottom flask 4 , disperse it in 10ml of freshly steamed THF, add dropwise 101mg of compound 3a (0.37mmol) in 3ml of freshly steamed THF solution at room temperature, stir the reaction at room temperature (24-26°C) for 30 minutes, and use TLC to track and measure the reaction degree of completion. After the reaction is complete, carefully add 0.5ml of water, continue stirring for 10 minutes, dilute with water, extract with ethyl acetate, and wash the organic phase with anhydrous Na 2 SO 4 After drying and concentration to remove the solvent, 2b was obtained.

[0048] The second step: add 68mg compound 2a, 20ml chloroform in 50ml round bottom flask, add active MnO under stirring 2 122mg, stirred at room temperature (24-26°C) for 5 hours, followed by TLC to deter...

Embodiment 2

[0051] Embodiment 2: the preparation of compound 5b:

[0052] [Chemical Reaction Formula 5]

[0053]

[0054] According to the above chemical reaction formula:

[0055] The first step: Compound 2b was prepared in the same manner as the first step of Example 1, except that the raw material 1a in the first step in Example 1 was replaced by raw material 1b.

[0056] Second step: Compound 3b was prepared in the same manner as the second step of Example 1, except that raw material 2b was used instead of raw material 2a in the second step of Example 1.

[0057] The third step: add 34mg of compound 3b (0.28mmol), 60mg of compound 4b (0.28mmol), 100mg of AcONa, 2ml of glacial acetic acid in a 5ml round bottom flask, reflux under nitrogen protection (100°C to 120°C) for 2 hours, and track the reaction by TLC . After the reaction was completed, it was cooled, filtered, washed and dried in vacuo to obtain 42 mg of compound 5b.

[0058] Compound 5b: 1H NMR (CDCl3, 300MHz) δ1.27~1...

Embodiment 3

[0059] Embodiment 3: the preparation of compound 5c:

[0060] Compound 5c was prepared in the same manner as in Example 1, except that the corresponding carboxylic acid or carboxylic acid ester and carbonyl compound were used as raw materials.

[0061] The structural formula of compound 5c:

[0062]

[0063] Compound 5c: 1 H NMR (DMSO-d 6 , 300MHz) δ2.32(s, 6H), 3.66(s, 3H), 3.75(s, 3H), 3.93(s, 2H), 6.78(d, 1H), 6.93(d, 1H), 7.01(s , 1H), 7.09 (s, 1H), 7.63 (s, 1H), 7.73 (s, 1H), 7.83 (d, 1H).

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PUM

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Abstract

This invention relates to a micromolecular organic compound that is used for activator of human embran mononucleotide activator protein kinase (AMPK). This compound can be used to prevent, postpone or cure diseases that are mediated by AMPK, especial type II diabetes, obesity and tumor. This invention also relates to the preparation of this compound. Otherwise, this invention also relates to application of this compound for activating human embran mononucleotide activator protein kinase or promoting intracellular amylaceum absorbing and application for preparing medicine that cure metabolic disease.

Description

technical field [0001] The invention relates to a small molecule organic compound which can be used as an activator of human adenosine mononucleotide-activated protein kinase (AMPK). The compounds can be used for preventing, delaying progression or treating diseases mediated by AMPK, especially type II diabetes, obesity and tumors. The present invention also relates to the preparation method of the compound. In addition, the present invention also relates to the application of the compound in activating human-derived adenosine mononucleotide-activated protein kinase and promoting intracellular glucose absorption and in the preparation of drugs for treating metabolic diseases. Background technique [0002] Diabetes has become one of the three major diseases that endanger human health. According to the statistics of the World Health Organization, there were 124 million diabetics in the world in 1997, and it is expected to rise to 300 million by 2025, of which 97% are type II ...

Claims

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Application Information

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IPC IPC(8): C07D413/06C07D413/14C07D417/06C07D417/14A61P3/00A61P3/10A61P3/04
CPCC07D409/06A61P3/00A61P3/04A61P3/10A61P35/00
Inventor 南发俊李佳刘冰庞涛于丽芳李静雅
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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