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Indole compound with antivirus activity in radix isatidis and derivative of indole compound

A compound and selected technology, applied in the field of medicine, can solve the problems of undiscovered anti-HIV and anti-influenza virus activity and the like

Active Publication Date: 2017-09-19
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] In addition, there are also literatures reporting complex structural derivatives of indole nitrogen atoms substituted with alkoxy groups and their cytotoxic activity. [39] , but they were not found to have anti-HIV and anti-influenza virus activity

Method used

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  • Indole compound with antivirus activity in radix isatidis and derivative of indole compound
  • Indole compound with antivirus activity in radix isatidis and derivative of indole compound
  • Indole compound with antivirus activity in radix isatidis and derivative of indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0228] Embodiment 1: Preparation of 2-(1-hydroxyl-1H-indol-3-yl)-N-phenylacetamide

[0229]

[0230] In the first step, weigh indole acetic acid (1.05g), add dichloromethane (20mL) to suspend and stir, add EDCI (1.27g) at room temperature, stir and dissolve; add aniline (0.62g), DMAP (0.15g), Stir the reaction at room temperature for 3 h; add 2N hydrochloric acid and stir rapidly for 10 min, and separate the phases; add saturated brine (10 mL) to the organic phase and stir for 10 min, and separate the phases; -indol-3-yl)-N-phenylacetamide.

[0231] In the second step, 2-(1H-indol-3-yl)-N-phenylacetamide was dissolved in trifluoroacetic acid (10mL), triethylsilane (1.74g) was added, and the reaction was refluxed at 60°C for 3h; the reaction solution Recover the solvent, add ethyl acetate (30mL), saturated aqueous sodium bicarbonate (30mL), stir rapidly for 15min, and separate the phases; extract the aqueous phase with ethyl acetate (30mL), and separate the phases; combine ...

Embodiment 2

[0233] Embodiment 2: Preparation of ethyl-2-[2-(1-hydroxyl-1H-indol-3-yl)acetamide]benzoate

[0234]

[0235] The first step, weigh indole acetic acid (1.05g), add dichloromethane (20mL) to suspend and stir, add EDCI (1.27g) at room temperature, stir to dissolve; add ethyl anthranilate (1.09g), DMAP (0.15g), stirred at room temperature for 3h; added 2N hydrochloric acid and stirred quickly for 10min, and separated the phases; added saturated brine (10mL) to the organic phase and stirred for 10min, and separated the phases; the organic phase was removed under reduced pressure at 40°C to obtain light reddish-brown oil Crude ethyl-2-[2-(1H-indol-3-yl)acetamide]benzoate.

[0236]In the second step, ethyl-2-[2-(1H-indol-3-yl)acetamide]benzoate was dissolved in trifluoroacetic acid (10mL), triethylsilane (1.74g) was added, 60 Reflux reaction at ℃ for 3h; the solvent was recovered from the reaction solution, ethyl acetate (30mL) and saturated aqueous sodium bicarbonate (30mL) wer...

Embodiment 3

[0238] Embodiment 3: the preparation of methyl-3-[2-(1-hydroxyl-1H-indol-3-yl)acetamide]-4-methylbenzoate

[0239]

[0240] The first step, weigh indole acetic acid (1.05g), add dichloromethane (20mL) to suspend and stir, add EDCI (1.27g) at room temperature, stir to dissolve; add 4-methyl-3-amino-benzoic acid methyl Ester (1.09g), DMAP (0.15g), stirred at room temperature for 3h; added 2N hydrochloric acid and stirred rapidly for 10min, and separated the phases; added saturated brine (10mL) to the organic phase and stirred for 10min, and separated the phases; the organic phase was removed under reduced pressure at 40°C , to obtain crude methyl-3-[2-(1H-indol-3-yl)acetamide]-4-methylbenzoate as light reddish brown oil.

[0241] In the second step, methyl-3-[2-(1H-indol-3-yl)acetamide]-4-methylbenzoate was dissolved in trifluoroacetic acid (10mL), and triethylsilane ( 1.74 g), reflux at 60°C for 3 h; the solvent was recovered from the reaction solution, ethyl acetate (30 mL...

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PUM

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Abstract

The invention discloses an indole compound extracted from radix isatidis shown in a general formula (I) and a derivative of the indole compound, as well as a salt acceptable on pharmacy, a preparation method of the compound, and a medicinal composite. The compound has apparent HIV-resisting activity and influenza virus-resisting activity, and can be used for preparing drugs or healthcare products for resisting HIV or influenza viruses. (The formula is shown in the description.).

Description

technical field [0001] The present invention relates to an indole derivative and its pharmaceutically acceptable salt, their preparation method, a pharmaceutical composition containing this type of compound, and the application of this type of compound in anti-HIV virus and anti-influenza virus, belonging to field of medical technology. Background technique [0002] Human Immunodeficiency Virus (Human Immunodeficiency Virus, HIV) infects human immune cells and destroys the human immune system, causing patients to eventually die of complications such as severe infection or secondary tumors. The disease caused by the virus is called Acquired Immunodeficiency Syndrome, or AIDS [1] . [0003] According to the report of the United Nations Program on AIDS (UNAIDS), by the end of 2012, the number of HIV-infected people in the world was 35 million [32.2 million-38.8 million], including 3.3 million children [3 million-3.7 million]. In 2012, there were 2.3 million [1.9 million-2.7 ...

Claims

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Application Information

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IPC IPC(8): C07D209/18C07D401/12C07D209/30A61K31/405A61K31/4439A61P31/18A61P31/16
CPCC07D209/18C07D209/30C07D401/12
Inventor 石建功郭颖徐成博霸明宇陈明华陈勍朱承根杨颖蒋建东曹颖莉郭庆兰张超林生唐克杨永春郭家梅
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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