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Preparation method and use of N-4-trifluoromethylphenylsalicylamide derivatives

A technology of trifluoromethyl phenyl salicylic amide and N-4- is applied in the field of preparation of N-4-trifluoromethyl phenyl salicylic amide derivatives, and can solve the problems of poor oral bioavailability and the like, To achieve the effect of good anti-tuberculosis bacteria activity, good anti-tuberculosis activity, and easy operation

Inactive Publication Date: 2015-09-02
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor oral bioavailability of niclosamide itself limits its further development and application.

Method used

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  • Preparation method and use of N-4-trifluoromethylphenylsalicylamide derivatives
  • Preparation method and use of N-4-trifluoromethylphenylsalicylamide derivatives
  • Preparation method and use of N-4-trifluoromethylphenylsalicylamide derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The structural formula of compound 11 is:

[0047]

[0048] The chemical reaction equation for the preparation of compound 11 is:

[0049]

[0050]The preparation method of compound 11 comprises the following steps:

[0051] 2-Hydroxy-5-methoxyformylbenzoic acid (0.2g, 1.0mmol) and p-trifluoromethylaniline (0.15mL, 1.2mmol) were dissolved in xylene and heated to 110°C under argon atmosphere Add PCl dropwise 3 (0.09mL, 1.0mmol), at this time the system changed from colorless and clear to yellow turbid state. React at 110°C for 3 hours, wait for the reaction system to cool down to room temperature, add a large amount of ethyl acrylate (EA) to dissolve, wash the organic phase with saturated saline and water, collect the organic phase, dry and concentrate, column chromatography gives light yellow Compound 11, the mass is 0.14g, and the yield is 41.2%.

[0052] The proton nuclear magnetic resonance spectrum data of compound 11 is:

[0053] 1 H-NMR: (400MHz, d-CHC...

Embodiment 2

[0055] The structural formula of compound 12 is:

[0056]

[0057] The chemical reaction equation for the preparation of compound 12 is:

[0058]

[0059] The preparation method of compound 12 is:

[0060] 2-Hydroxy-5-acetylbenzoic acid (1.0mmol) and p-trifluoromethylaniline (0.15mL, 1.2mmol) were dissolved in xylene, heated to 130°C, and PCl was added dropwise under argon atmosphere 3 (0.09mL, 1.0mmol), at this time the system changed from colorless and clear to yellow turbid state. React at 130°C for 3 hours, wait for the reaction system to cool to room temperature, add a large amount of ethyl acrylate (EA) to dissolve, wash the organic phase with saturated saline and water, collect the organic phase, dry and concentrate, column chromatography gives light yellow The solid, that is, compound 12, has a mass of 0.14 g and a yield of 41.2%.

[0061] The proton nuclear magnetic resonance spectrum data of compound 12 is:

[0062] 1 H-NMR: (400MHz, d-CHCl 3 )12.48(s, 1H...

Embodiment 3

[0064] The structural formula of compound 13 is:

[0065]

[0066] The chemical reaction equation for the preparation of compound 13 is:

[0067]

[0068] The preparation method of compound 13 is:

[0069] 2-Hydroxy-5-nitrobenzoic acid (1.0mmol) and p-trifluoromethylaniline (0.15mL, 1.2mmol) were dissolved in xylene and heated to 120°C, and PCl was added dropwise in an argon atmosphere 3 (0.09mL, 1.0mmol), at this time the system changed from colorless and clear to yellow turbid state. React at 120°C for 3 hours, wait for the reaction system to cool to room temperature, add a large amount of ethyl acrylate (EA) to dissolve, wash the organic phase with saturated saline and water, collect the organic phase, dry and concentrate, column chromatography gives light yellow The solid, namely compound 13, yielded 66.2%.

[0070] The proton nuclear magnetic resonance spectrum data of compound 13 is:

[0071] 1 H-NMR: (400MHz, d-DMSO) 10.83(s, 1H), 8.68(s, 1H), 8.29(d, J=9.2Hz...

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Abstract

The invention discloses a preparation method and use of N-4-trifluoromethylphenylsalicylamide derivatives shown in a general formula (I). The preparation method of the N-4-trifluoromethylphenylsalicylamide derivatives or pharmaceutically acceptable salt thereof has the advantages of easy acquisition of raw materials and operation easiness and is suitable for industrial production. The N-4-trifluoromethylphenylsalicylamide derivatives have good inhibition effects on growth of a tubercle bacillus standard strain H37Rv and clinical drug-resistant tubercle bacillus, can be used in preparation of an antitubercular drug and has the lowest bacteriostasis concentration of 5 micrograms per milliliter.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method and application of N-4-trifluoromethylphenyl salicylamide derivatives. Background technique [0002] Tuberculosis (TB) is caused by Mycobacterium tuberculosis (Mtb) infection and is one of the most prevalent diseases in the world. Among human tuberculosis, the most common is pulmonary tuberculosis. Due to the emergence of drug-resistant tuberculosis and the concurrent infection of AIDS, coupled with the lack of new anti-tuberculosis drugs in the past forty years, it is difficult to treat tuberculosis. [0003] At present, about 2 billion people in the world are infected with tuberculosis, and about 8-10 million new tuberculosis patients appear every year, and about 2-3 million deaths due to tuberculosis every year. my country is one of the 22 countries with severe tuberculosis epidemics in the world, and it is also one of the 27 countries with severe mult...

Claims

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Application Information

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IPC IPC(8): A61K31/609C07C237/44C07C235/64C07C235/84C07C231/02A61P31/06
Inventor 丁克陆小云张天宇汤健鲁明辉李宇鹏张章梁镇兴钱政江
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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