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Compounds and application thereof in preparation of anti-parasitosis drugs

A technology of compound and ketone compound, applied in the field of application in the preparation of antiparasitic drugs

Inactive Publication Date: 2015-07-08
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] None of the existing antimalarial drugs can kill all stages of the life cycle of Plasmodium, and different antimalarial drugs act on different stages

Method used

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  • Compounds and application thereof in preparation of anti-parasitosis drugs
  • Compounds and application thereof in preparation of anti-parasitosis drugs
  • Compounds and application thereof in preparation of anti-parasitosis drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Example 1. Preparation of compound 1

[0143] The reaction equation is as follows:

[0144]

[0145] Under argon protection, weigh 1.5g of p-bromomethylacetophenone, 2g of p-trifluoromethoxyphenylboronic acid, 32mg of palladium acetate, 74mg of triphenylphosphine and 3g of potassium phosphate into a 100ml round-bottom flask, add 20ml Toluene was reacted at 80°C for 8 hours under argon protection, the solvent was spin-dried under reduced pressure, the residue was dissolved in 20 ml of dichloromethane, washed twice with water, dried over anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, and the residue was used Petroleum ether:ethyl acetate=30:1 (volume ratio) was passed through a silica gel column to obtain 1.7 g of intermediate A1 (intermediate A1 was a light yellow liquid) with a yield of 81%.

[0146] Take 1g of ethyl o-chlorobenzoate in a 100ml round-bottomed flask, add 20ml of dry tetrahydrofuran to dissolve; weigh 200mg of sodium hydrid...

Embodiment 2

[0150] Example 2, the preparation of compound 2

[0151] The reaction equation is as follows:

[0152]

[0153] Take 1.2g of methyl 2,4-dichlorobenzoate in a 100ml round-bottomed flask, add 20ml of dry tetrahydrofuran to dissolve; weigh 200mg of sodium hydride and add it to the above solution, and stir at 50°C. Take 1 g of intermediate A1 and dissolve it in 5 ml of dry tetrahydrofuran solution, and slowly add the tetrahydrofuran solution of intermediate A1 dropwise to the above solution stirred at 50 °C; then increase the temperature to 80 °C, reflux for about 10h to The reaction ends. The solvent was spin-dried under reduced pressure, the residue was dissolved in dichloromethane, washed twice with water, dried with anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, and the residue was washed with petroleum ether:ethyl acetate=20:1 (volume ratio) Silica gel column to obtain 842 mg of intermediate A3 (intermediate A3 is a light yellow liquid) in a...

Embodiment 3

[0158] Example 3, the preparation of compound 3

[0159] The reaction equation is as follows:

[0160]

[0161] Take 1.3g of 2,6-dichlorobenzoyl chloride in a 100ml round-bottomed flask, add 20ml of dry tetrahydrofuran to dissolve; weigh 200mg of sodium hydride and add it to the above solution, and stir at 50°C. Take 1 g of intermediate A1 and dissolve it in 5 ml of dry tetrahydrofuran solution, and slowly add the tetrahydrofuran solution of intermediate A1 dropwise to the above solution stirred at 50 °C; then increase the temperature to 80 °C, reflux for about 10h to The reaction ends. The solvent was spin-dried under reduced pressure, the residue was dissolved in dichloromethane, washed twice with water, dried with anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, and the residue was washed with petroleum ether:ethyl acetate=20:1 (volume ratio) Silica gel column to obtain 541 mg of intermediate A4 (intermediate A4 is a light yellow liquid) in ...

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Abstract

The invention discloses compounds and an application thereof in preparation of anti-parasitosis drugs. The compounds have a structural formula represented by the formula I or the formula II. The compounds provided by the invention have rich functional group diversity and modificability, and the products are relatively easy to separate and purify. The compounds provided by the invention have quite good inhibitory effect on pernicious malaria NDH protein activity and are new anti-malarial action targets and mechanisms, and thus the compounds also have quite good inhibitory effect on many plasmodium species and strains generating resistance to traditional drugs, thereby providing a new breakthrough for current increasingly-serious plasmodium drug resistance aspect. At the same time, the plasmodium NDH and human NADH oxidordeuctase belong to different species, so that the compounds can be expected to produce fewer side effects on human. In summary, the compounds have broad development and application prospects.

Description

technical field [0001] The present invention relates to a compound and its application in the preparation of antiparasitic medicines. Background technique [0002] Malaria is a global acute infectious disease caused by Plasmodium falciparum and transmitted by Anopheles mosquitoes. It is the most harmful parasitic disease to humans. The pathogenic Plasmodium mainly includes Plasmodium vivax, Plasmodium malaria, Plasmodium ovale and Plasmodium falciparum, which cause Plasmodium vivax, Plasmodium malaria, Plasmodium ovale and Plasmodium falciparum respectively. The first three are also known as benign malaria , Plasmodium falciparum is the most widely infected, with severe symptoms and the greatest harm to human health. Worldwide, there are as many as 300 million malaria patients and millions of deaths each year. [0003] None of the existing antimalarial drugs can kill all stages of the life cycle of Plasmodium, and different antimalarial drugs act on different stages. [0...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D401/04C07D215/56C07D215/233C07D215/42A61K31/352A61K31/4709A61K31/47A61P33/06
CPCC07D215/233C07D215/42C07D215/56C07D311/30C07D401/04Y02A50/30
Inventor 饶燏杨茂君杨毅庆李小璐
Owner TSINGHUA UNIV
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