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Acetylsalicylic acid-pyrazinamide hybrid as well as preparation method and application thereof

A technology of acetylsalicylic acid and pyrazinamide, which is applied in the fields of organic chemistry and antibacterial drugs, can solve the problem of uncertain specific action targets of pyrazinamide, and achieve the prevention of drug resistance of Mycobacterium tuberculosis, strong activity, and improved The effect of curative effect

Inactive Publication Date: 2018-12-21
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the specific target of pyrazinamide is still uncertain. From the perspective of enzyme kinetics, Ngo et al. pointed out that pyrazinamide, pyrazinic acid and halogenated pyrazinamide can inhibit the purified Mycobacterium fatty acid synthase I (FASI), and FASI can As a potential target for researching new drugs against tuberculosis
No similar studies have been published

Method used

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  • Acetylsalicylic acid-pyrazinamide hybrid as well as preparation method and application thereof
  • Acetylsalicylic acid-pyrazinamide hybrid as well as preparation method and application thereof
  • Acetylsalicylic acid-pyrazinamide hybrid as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] 1) Weigh 0.8 g of acetylsalicylic acid, add it together with 7 mL of dichloromethane into a 100 mL single-necked bottle, and stir at room temperature for 30 min. After the acetylsalicylic acid is fully dissolved, add 3ml of thionyl chloride (SOCl 2 ) and stirred at room temperature for 30 min, then added dropwise 1 drop of DMF, and after stirring found that gas was slowly generated, the temperature was raised to 40° C. for reflux reaction for 3 hours, and finally the crude product of acetylsalicylic acid chloride was obtained by distillation under reduced pressure.

[0033] 2) Put 0.5 g of pyrazinamide and 40 mL of chloroform in a three-necked flask, raise the temperature to 39° C. to fully dissolve, and then add 1 mL of triethylamine to obtain a pyrazinamide reaction solution.

[0034] 3) Add the crude product of acetylsalicylic acid chloride obtained in step 1 into 2 ml of dichloromethane for dilution to obtain a reaction solution of acetylsalicylic acid chloride. Th...

Embodiment 2

[0038]1) Weigh 1.0 g of acetylsalicylic acid, add it together with 10 mL of dichloromethane into a 100 mL single-necked bottle, and stir at room temperature for 30 min. After the acetylsalicylic acid is fully dissolved, add 5ml of thionyl chloride (SOCl 2 ) and stirred at room temperature for 30 min, then added dropwise 1 drop of DMF, and after stirring found that gas was slowly generated, the temperature was raised to 40° C. for reflux reaction for 3 hours, and finally the crude product of acetylsalicylic acid chloride was obtained by distillation under reduced pressure.

[0039] 2) Put 0.5 g of pyrazinamide and 40 mL of chloroform in a three-necked flask, raise the temperature to 40° C. to fully dissolve, and then add 1 mL of triethylamine to obtain a pyrazinamide reaction solution.

[0040] 3) Add the crude product of acetylsalicylic acid chloride obtained in step 1 into 2 ml of dichloromethane for dilution to obtain a reaction solution of acetylsalicylic acid chloride. Th...

Embodiment 3

[0044] 1) Weigh 1.0 g of acetylsalicylic acid, add it together with 10 mL of dichloromethane into a 100 mL single-necked bottle, and stir at room temperature for 30 min. After the acetylsalicylic acid is fully dissolved, add 5ml of thionyl chloride and stir at room temperature for 30 minutes, then add 1 drop of DMF dropwise, after stirring and find that gas is slowly generated, heat up to 40°C for reflux for 3 hours, and finally reduce Distilled under high pressure to obtain the crude product of acetylsalicylic acid chloride.

[0045] 2) Put 0.6 g of pyrazinamide and 40 mL of chloroform in a three-necked flask, raise the temperature to 40° C. to fully dissolve, and then add 1 mL of triethylamine to obtain a pyrazinamide reaction solution.

[0046] 3) Add the crude product of acetylsalicylic acid chloride obtained in step 1 into 2 ml of dichloromethane for dilution to obtain a reaction solution of acetylsalicylic acid chloride. Then slowly add the acetylsalicylic acid chloride...

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Abstract

The invention relates to an acetylsalicylic acid-pyrazinamide hybrid as well as a preparation method and application thereof in an antituberculosis aspect. Firstly, acetylsalicylic acid and thionyl chloride are used as raw materials to synthesize acetylsalicylic chloride, and then the acetylsalicylic chloride reacts with pyrazinamide to obtain a target product acetylsalicylic acid-pyrazinamide hybrid. The acetylsalicylic acid-pyrazinamide hybrid provided by the invention has the advantages that applicable sites are more, the specificity is strong, side effects are less, the drug resistance isunlikely to generate, the tuberculosis treatment effect can be improved, toxic and side effects of acetylsalicylic acid and pyrazinamide are reduced, the effect of each pharmacological activity is developed to make good for deficiency, and the drug resistance of mycobacterium tuberculosis can be relieved and even prevented.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical synthesis, in particular to a novel anti-tuberculosis drug-acetylsalicylic acid-pyrazinamide hybrid and its preparation method and application. Background technique [0002] As early as ancient Greece and Rome, people extracted salicylic acid from willow and poplar bark, and found that it can be used as analgesic, antipyretic and anti-inflammatory drugs, but salicylic acid will damage the oral and esophageal mucosa, and then It has a greater stimulating effect on the stomach. In 1898, German chemist Felix Hoffmann (Felix Hoffmann) successfully synthesized an effective drug that could replace salicylic acid—acetylsalicylic acid (also known as aspirin, molecular weight 180.16), and in 1900 in Germany Bayer company Start production. So far, aspirin is still widely used antipyretic, pain relief, good medicine for treating colds. In addition, scientists have found that aspirin also has new fu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/24A61P31/04
CPCA61P31/04C07D241/24
Inventor 祝宏李雪张焕李丽曾祥聪丁娇
Owner WUHAN INSTITUTE OF TECHNOLOGY
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