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N-(4-substituted phenylethyl)acetamide compounds and their use

A technology of amide compounds and phenethyl, applied in the field of N-acetamide compounds

Active Publication Date: 2019-10-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The crystal structure of falcipain-3 has not been reported

Method used

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  • N-(4-substituted phenylethyl)acetamide compounds and their use
  • N-(4-substituted phenylethyl)acetamide compounds and their use
  • N-(4-substituted phenylethyl)acetamide compounds and their use

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preparation example Construction

[0041] The method for the compound shown in the preparation formula I provided by the invention specifically comprises the following steps:

[0042] (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, add 4-nitrophenethylamine hydrochloride, then react at room temperature for 24 hours, stop the reaction, add water to the reaction solution, and use ethyl acetate Esters were extracted, concentrated, and the solvent was distilled off under reduced pressure, the residue was washed with water, and then extracted with ethyl acetate, and the organic phase was purified by silica gel column chromatography to obtain the compound shown in formula II;

[0043] (2) the compound shown in formula II is dissolved in methanol, under stirring, add 10% palladium c...

Embodiment 1

[0049] N-(4-(((2,4-diaminopyrimidin-5-yl)methyl)amino)phenethyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-formamide (marked as "I A -1") Preparation:

[0050] (1) Preparation of N-(4-nitrophenethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-carboxamide (compound shown in formula II-1) :

[0051]

[0052] Dissolve 1.80g (10mmol) of 1,4-benzodioxane-6-carboxylic acid in 50ml of dichloromethane, and add 3.8g (20mmol) of 1-ethyl-(3-dimethylaminopropyl) under stirring ) carbodiimide hydrochloride, 2.7g (20mmol) 1-hydroxybenzotriazole, after reacting at room temperature for 1h, add 3.3mL (20mmol) N,N-diisopropylethylamine, 0.122g (1mmol) 4-Dimethylaminopyridine, add 2.03g (10mmol) 4-nitrophenethylamine hydrochloride, react at room temperature for 24h, then add an appropriate amount of water, extract with ethyl acetate, wash the organic phase with saturated brine, and concentrate the organic phase. phase (removal of solvent by distillation under reduced pressure), and the residue was separate...

Embodiment 2

[0069] N-(4-(((2,4-diaminopyrimidin-5-yl)methyl)amino)phenethyl)benzo[d][1,3]dioxolane (labeled " I A -2") Preparation:

[0070] In addition to replacing 1,4-benzodioxane-6-carboxylic acid with benzo[d][1,3]dioxolanecarboxylic acid in step (1) of Example 1, all other Need raw material, reagent and preparation method with embodiment 1, obtain white solid (I A -2), yield 50%.

[0071] 1H NMR (400MHz, DMSO) δ8.35(t, J=5.5Hz, 1H), 7.64(s, 1H), 7.41(dd, J=8.1, 1.7Hz, 1H), 7.36(d, J=1.6Hz ,1H),6.95(dd,J=15.1,8.3Hz,3H),6.52(d,J=8.4Hz,2H),6.46(s,1H),6.08(s,2H),6.03(s,2H) ,5.68(s,1H),3.89(d,J=5.2Hz,2H),3.34(s,3H),2.71–2.59(m,2H).

[0072] HRMS(EI)m / z calce C 21 h 22 N 6 o 3 (M + ) 406.1753 (theoretical value), found 406.1753.

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Abstract

The present invention relates to acetamide compounds and uses thereof. The invention discloses a class of N-(4-substituted phenylethyl) amides compounds with novel structure. The in vitro activity test experiment shows that the compound has enzyme inhibitory activity on cysteine ​​protease (FP‑2) and dihydrofolate reductase (DHFR). And the results of in vitro malaria killing experiments show that the compounds have inhibitory effects on both wild and drug-resistant Plasmodium.

Description

technical field [0001] The invention relates to acetamide compounds and uses thereof, in particular to a class of N-(4-substituted phenethyl)acetamide 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 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C07D401/12C07D409/12C07D239/48A61P33/06
CPCC07D239/48C07D401/12C07D405/12C07D409/12Y02A50/30
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