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3-methoxy-4-(N-substituted amino sulfonyl)fenalamide compounds and application thereof

A technology based on phenylpropanamide and sulfamoyl, which is applied in the field of 3-methoxy-4-phenylpropanamide compounds and can solve problems affecting the function of oocysts

Inactive Publication Date: 2011-06-08
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

FP-1 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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  • 3-methoxy-4-(N-substituted amino sulfonyl)fenalamide compounds and application thereof
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  • 3-methoxy-4-(N-substituted amino sulfonyl)fenalamide compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Methyl 3-methoxyphenylpropionate (IV)

[0056] Dissolve 1.5 g of 3-methoxyphenylpropionic acid in an eggplant-shaped flask filled with 40 mL of anhydrous methanol, slowly add about 1 mL of concentrated sulfuric acid dropwise to the system with stirring at room temperature, and heat to 70°C for 5 hours under reflux. Cooled to room temperature, the methanol solvent in the system was distilled off under reduced pressure, followed by saturated NaHCO 3 The solution was washed, and the system was adjusted to pH=7. Extracted with ethyl acetate (20 mL×3), combined the obtained organic layers, and washed with distilled water (10 mL×3). The organic layer was dried with anhydrous magnesium sulfate, suction filtered, and the solvent was distilled off under reduced pressure to obtain 1.4 g of yellow oil (IV), with a yield of 87%.

Embodiment 2

[0058] Methyl 3-methoxy-4-chlorosulfonylphenylpropionate (V)

[0059] 1 mL of chlorosulfonic acid was slowly added dropwise to an eggplant flask containing 1.4 g of methyl 3-methoxyphenylpropionate. Control the rate of addition, keep the temperature of the reaction solution not higher than 40°C, stir for 5 hours, pour the reaction system into a beaker filled with ice cubes, extract with ethyl acetate (20mL × 3), mix the organic layer obtained, and then Wash with distilled water (10 mL×3). The organic layer was dried with anhydrous magnesium sulfate, suction filtered, and the solvent was distilled off under reduced pressure to obtain 1.4 g of light yellow oil (V), with a yield of 66%. 1 H-NMR (400Hz, CDCl 3 ), δ: 2.77(2H, t), 3.43(2H, t), 3.71(3H, s), 3.90(3H, s), 6.89(1H, d), 6.95(1H, d), 8.04(1H, d).

Embodiment 3

[0061] Methyl 3-methoxy-4-(N-(2-methyl-4-nitro)sulfamoyl)phenylpropionate (VI)

[0062] Dissolve 0.78 g of 2-methyl-4-nitroaniline in 20 mL of distilled anhydrous tetrahydrofuran, and add 2 mL of anhydrous pyridine, then add 1.4 g of 3-methoxy-4-chlorosulfonylphenylpropionic acid A solution of methyl ester (V) in anhydrous tetrahydrofuran (10 mL) was added dropwise to the above system. The whole reaction system N 2 Reflux overnight at 70°C under protection. The reaction was monitored by thin-layer chromatography, and after the reaction of the raw material (V) was complete, it was cooled to room temperature. Tetrahydrofuran in the system was distilled off under reduced pressure, dissolved in dichloromethane, and then washed with distilled water (20 mL×3) to remove a small amount of residual pyridine. The dichloromethane layer was dried with anhydrous magnesium sulfate, suction filtered, and the solvent was distilled off under reduced pressure, and the obtained oily mixture w...

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Abstract

The invention relates to a preparation method and pharmacological application of novel 3-methoxy-4-(N-substituted amino sulfonyl)fenalamide derivatives. The structural general formula of the derivatives is shown in a formula (I), wherein R1 and R2 are defined as the specifications. The compounds can serve as small molecular double inhibitors for Falcipain-2 and dihydrofolate reductase (DHFR), simultaneously blocks hemoglobin hydrolysis under the action of cysteine protease and inhibits the reduction activity of the DHFR, so as to inhibit multiplication of plasmodium. Therefore, the compounds can be expected to be developed into double-target-based novel antimalarial medicines.

Description

technical field [0001] The invention relates to 3-methoxy-4-(N-substituted sulfamoyl) phenylpropanamide compounds, a preparation method and application thereof. Background technique [0002] Malaria (Malaria) is one of the most prominent problems in public health in the world today, and it is the most widespread and harmful parasitic disease in the world. According to the World Health Organization (WHO) report statistics in 2008, there are 109 countries and regions in the world that are endemic areas of malaria, about 40% of the population is threatened by malaria, 59% of the global malaria cases are distributed in Africa, 38 % distributed in Asia, 3% distributed in the Americas. Although malaria is very rare in Europe, cases of P. falciparum malaria without travel history or blood transfusion history have been detected in a few Western European countries in 2006. Every year, 350 million to 500 million people are infected with malaria, 2.7 million people die from malaria, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/29C07D213/40C07D233/64C07D333/20C07D307/52C07D209/14A61K31/18A61K31/4406A61K31/417A61K31/381A61K31/4402A61K31/341A61K31/4045A61P33/06
CPCY02A50/30
Inventor 李剑黄瑾李洪林张钰卢伟强李蹊辛伟刘晓峰沈旭蒋华良
Owner EAST CHINA UNIV OF SCI & TECH
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