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Benzene alkyl amides compound and usage thereof

A technology of benzalkonium compounds and compounds is applied in the field of benzalkonium compounds and can solve problems such as affecting the function of oocysts

Inactive Publication Date: 2009-12-02
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Falcipain1 is the first expressed Plasmodium cysteine ​​protease, and its biological research shows that it has no effect on the asexual reproduction stage of Plasmodium, but can significantly affect the function of oocysts

Method used

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  • Benzene alkyl amides compound and usage thereof
  • Benzene alkyl amides compound and usage thereof
  • Benzene alkyl amides compound and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of methyl 3-phenylpropionate (compound II-1)

[0055] Dissolve 3.0 g of 3-phenylpropionic acid in a 50 mL round-bottomed flask filled with 30 mL of anhydrous methanol, heat to reflux at 70°C, then cool to 20°C-30°C, control this temperature, and slowly dissolve 1 mL of concentrated sulfuric acid under stirring Add it dropwise to the reaction liquid, raise the temperature to 70°C, and reflux for 5 hours. Remove the solvent by distillation under reduced pressure, add 30 mL of ethyl acetate, wash with distilled water (10 mL×3), 5% sodium bicarbonate (10 mL×3), and distilled water (10 mL×3) successively, and dry the ethyl acetate layer with anhydrous magnesium sulfate , filtered, and the solvent was removed under reduced pressure to obtain 2.9 g of methyl 3-phenylpropionate (II-1) as a colorless liquid with a yield of 88%. MS (EI) m / z 164 (M + ).

Embodiment 2

[0057] Preparation of methyl 3-(4-chlorosulfonylphenyl)propionate (compound III-1)

[0058] Add 5.5 mL of chlorosulfonic acid dropwise to 2.9 g of methyl 3-phenylpropionate (II-1), control the rate of addition, keep the temperature of the reaction solution not higher than 40°C, and continue stirring for 1.5 hours after the addition. The reaction solution was poured into 80 mL of ice water, extracted with dichloromethane (30 mL×3), washed with brine (10 mL×3) and distilled water (10 mL×3) successively, the organic phase was dried with anhydrous magnesium sulfate, filtered, and removed under reduced pressure The solvent was used to obtain 3.3 g of methyl 3-(4-chlorosulfonylphenyl)propionate (III-1) as a white solid with a yield of 72%. mp 62-64°C; MS (EI) m / z 262 (M + ).

Embodiment 3

[0060] Preparation of methyl 3-(4-(N-phenethyl-sulfamoyl)phenyl)propionate (compound IV-1)

[0061] Add 1.0 g of 2-phenylethylamine to 20 mL of pyridine, stir at 20°C-30°C, and add 1.0 g of 3-(4-chlorosulfonylphenyl)propionic acid methyl ester (III-1) in batches to In the reaction solution, after the addition, continue to stir for 2 hours, remove the solvent under reduced pressure, add an appropriate amount of water and extract with dichloromethane, wash with 6N hydrochloric acid in turn, dry the dichloromethane with anhydrous magnesium sulfate, filter, and remove the solvent under reduced pressure 0.78 g of methyl 3-(4-(N-phenethyl-sulfamoyl)phenyl)propionate (IV-1) was obtained as light yellow liquid with a yield of 60%. MS (EI) m / z 347 (M + ).

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Abstract

The invention relates to a substituted benzene alkyl amides compound, i.e. 4-(N-substituted amino-sulfonyl) benzene alkyl amide compound and a usage thereof. The inventor makes comprehensive use of CADD and SPR experiment based on Biacore, finds the substituted benzene alkyl amides compound and applies a reasonable drug design method to modify the structure of the substituted benzene alkyl amides compound so as to finally obtain the 4-(N-substituted amino-sulfonyl) benzene alkyl amide compound; after tests, the obtained 4-(N-substituted amino-sulfonyl) benzene alkyl amide compound inhibits the activity of falcipain-2 in in-vitro enzyme level experimental tests; and the result shows that the 4-(N-substituted amino-sulfonyl) benzene alkyl amide compound has strong falcipain-2 activity inhibiting capability and can be used for preparing medicaments for treating malaria caused by plasmodium.

Description

technical field [0001] The present invention relates to phenylalanamide compounds and uses thereof, in particular to a substituted phenylalanamide compound, namely 4-(N-substituted sulfamoyl) phenylalanamide compounds and uses thereof. Background technique [0002] Malaria is one of the world's worst epidemics. About 3 billion people in more than 100 countries and regions are threatened by malaria. There are 350 to 500 million people who suffer from malaria every year in the world, and 1.5 to 2.7 million patients die from malaria every year, and about half of them are children. Although there are effective antimalarial drugs, the mortality rate of malaria patients is still increasing year by year. The main reason is that the Plasmodium that causes malaria has adapted to the limited antimalarial drugs, that is, it has developed severe drug resistance. [0003] Malaria control also relies heavily on the prevention and treatment of chemical drugs. In the past 70 years, only a...

Claims

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Application Information

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IPC IPC(8): C07D319/18C07D317/66C07D277/82C07D277/64C07D213/40C07C311/16C07D285/135A61K31/357A61K31/428A61K31/433A61K31/18A61P33/06
CPCY02A50/30
Inventor 蒋华良李剑黄瑾李洪林车鹏卢伟强朱进陈曈刘彦青庄静静陈莉莉沈旭洛夫希金弗
Owner EAST CHINA UNIV OF SCI & TECH
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