Acetamides compound and application thereof

A compound, acetamide technology, applied in the field of N-acetamide compounds

Active Publication Date: 2017-06-30
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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The crystal structure of falc

Method used

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  • Acetamides compound and application thereof
  • Acetamides compound and application thereof
  • Acetamides compound and application thereof

Examples

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preparation example Construction

[0045] The method for the compound shown in the preparation formula I provided by the invention specifically comprises the following steps:

[0046] (1) the carboxylic acid (R 2 COOH) was dissolved in dichloromethane and added 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1-hydroxybenzotriazole under stirring, reacted at room temperature for 1 hour and then added N , N-diisopropylethylamine, 4-dimethylaminopyridine, N,N-dimethylaniline, add 4-bromophenethylamine, react at room temperature for 24 hours, stop the reaction, extract with ethyl acetate , concentrated organic phase (decompression distillation to remove solvent), silica gel column chromatography purification, obtains the compound shown in formula II;

[0047] (2) Dissolve the compound represented by formula II in anhydrous tetrahydrofuran, add n-butyllithium at -78°C, react for 1 hour, then add N,N-dimethylformamide, return to room temperature, and wash with water , extracted with ethyl acetate, the...

Embodiment 1

[0053] N-(4-(((2,4-diaminoquinazolin-6-yl)amino)methyl)phenethyl)-4-nitrobenzamide (labeled "I A -1") Preparation:

[0054] (1) Preparation of N-(4-bromophenyl)-4-nitrobenzamide (compound shown in formula II-1)

[0055]

[0056] Dissolve 1.67g (10mmol) of 4-nitrobenzoic acid in 50ml of dichloromethane and add 3.8g (20mmol) of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride under stirring, 2.7g (20mmol) 1-hydroxybenzotriazole, after reacting at room temperature for 1 hour, add 2.58g (20mmol) N,N-diisopropylethylamine, 0.122g (1mmol) 4-dimethylaminopyridine, then add 2.0g (10mmol) 4-bromophenethylamine, reacted at room temperature for 24 hours, stopped the reaction, added water, extracted with ethyl acetate, concentrated the organic phase (removed solvent by distillation under reduced pressure), purified by silica gel column chromatography (elution The solution was ethyl acetate:petroleum ether=1:10, v / v), and a white solid (compound represented by formula II-1) ...

Embodiment 2

[0072] N-(4-(((2,4-diaminoquinazolin-6-yl)amino)methyl)phenethyl)-2,3-dihydrobenzo[b][1,4]dioxo Fen-6-carboxamide (marked as "I A -2") Preparation:

[0073] Except that 4-nitrobenzoic acid is replaced by 2,3-dihydrobenzo[b][1,4]dioxincarboxylic acid, all the other required raw materials, reagents and preparation methods are the same as in Example 1 to obtain a white solid ( I A -2).

[0074] 1 H NMR (400MHz, DMSO) δ8.95(t, J=7.0Hz, 1H), 8.60–8.31(m, 3H), 8.10–7.80(m, 2H), 7.50(m, 1H), 7.24(d, J=8.0Hz, 4H), 7.01(m, 5H), 6.31(t, J=5.6Hz, 1H), 4.21(d, J=5.8Hz, 2H), 3.32(dd, J=14.5, 6.5Hz, 4H), 3.17(d, J=4.8Hz, 1H), 2.84(t, J=7.5Hz, 2H).HRMS(EI) m / z calce C 26 h 26 N 6 o 3 (M + ) 470.2066 (theoretical value), experimental value (found) 470.2064.

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Abstract

The invention relates to an acetamides compound and application thereof, and discloses an N-(4-substituted phenyl ethyl) amides compound with a novel structure. An in vitro activity test experiment proves that the compound has the enzyme inhibitory activity on cysteine proteinase (FP-2) and dihydrofolate reductase (DHFR); a malaria-killing experiment result proves that the compound has an inhibition effect on wild and drug-resistant malaria protozoon.

Description

technical field [0001] The present invention relates to an acetamide compound and its use, in particular to an N-(4-substituted phenyl)acetamide compound and its use. 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 of malaria every year, about half of them are children, and 90% of them are children. Cases have occurred in poor countries in Africa and Asia. In my country, malaria-endemic areas mainly include 19 provinces, municipalities and autonomous regions including Hainan and Yunnan, and about millions of people get sick. Although there are effective antimalarial drugs, the mortality rate of malaria patients is increasing year by year, mainly because the malaria parasite quickly adapts to the limited antimalarial drugs and develops sev...

Claims

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Application Information

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IPC IPC(8): C07D239/95C07D405/12C07D409/12C07D401/12A61P33/06
CPCC07D239/95C07D401/12C07D405/12C07D409/12Y02A50/30
Inventor 朱进黄瑾陈文华姚雪凌大正王曼炯蒋华良李剑
Owner EAST CHINA UNIV OF SCI & TECH
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