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Amide derivative and purpose thereof

A technology of amide derivatives and formamide, which is applied in the field of amide derivatives and can solve problems affecting the function of oocysts

Inactive Publication Date: 2011-09-28
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Falcipain 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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  • Amide derivative and purpose thereof
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  • Amide derivative and purpose thereof

Examples

Experimental program
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preparation example Construction

[0036] Formula I A Preparation of the indicated compounds:

[0037] 1) Methyl 5-chloromethylfuran-2-carboxylate, R 3 OH (such as substituted aryl phenol), inorganic base and organic solvent are mixed, reflux overnight; most of the solvent is evaporated, water is added, organic solvent is extracted, dried, and the solvent is evaporated to dryness to obtain 5-(substituted aryloxymethyl)furan- Methyl 2-formate (compound represented by formula II).

[0038] 2) Put the compound II and inorganic base obtained in step 1) into an appropriate amount of methanol, and stir overnight at 50°C; evaporate most of the solvent, add water, adjust the pH to 1 with hydrochloric acid, precipitate a solid, and filter with suction to obtain 5-(substituted aryloxymethyl)furan-2-carboxylic acid (compound represented by formula III).

[0039] 3) R at room temperature 1 The substituted amine is reacted with p-acetamidobenzenesulfonyl chloride in an alkaline solution at a temperature of 40°C to 45°C ...

Embodiment 1

[0051] Preparation of methyl 5-(4-chloro-3-methylphenoxymethyl)furan-2-carboxylate (compound II-1)

[0052] Mix 2.5 g of 5-chloromethylfuran-2-methylcarboxylate, 2.2 g of 4-chloro-3-methylphenol, 2.6 g of potassium carbonate and 40 ml of acetonitrile, and reflux overnight; evaporate most of the solvent, add water, acetic acid Ethyl ester was extracted, the ester layer was dried, and the solvent was evaporated to dryness to obtain 3.8 g of white solid with a yield of 94.5%. mp 56-58°C; 1 H-NMR (DMSO-d 6 , 500MHz) δ2.29(s, 3H), 3.81(s, 3H), 5.14(s, 2H), 6.80(d, 1H), 6.91(dd, 1H), 7.07(d, 1H), 7.20(d , 1H), 7.30-7.33 (m, 2H); MS (EI) m / z 280 (M + ).

Embodiment 2

[0054] Preparation of 5-(4-chloro-3-methylphenoxymethyl)furan-2-carboxylic acid (compound III-1)

[0055] Put 1.7 g of II-1 and 0.5 g of lithium hydroxide monohydrate into 20 ml of methanol, and stir overnight at 50°C. Most of the solvent was evaporated, water was added, the pH was adjusted to 1 with hydrochloric acid, a solid was precipitated, and 1.58 g of white solid (III-1) was obtained by suction filtration, with a yield of 97.5%. mp 194-195°C; 1 H-NMR (DMSO-d 6 , 500MHz) δ2.28(s, 3H), 5.11(s, 2H), 6.74(d, 1H), 6.89(dd, 1H), 7.05(d, 1H), 7.20(d, 1H), 7.30(d , 1H); MS (EI) m / z 266 (M + ).

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Abstract

The invention relates to an amide derivative and a purpose thereof. The invention discloses an N-(4-substiguted aminoacyl phenyl)-5-substited furan-2-formamide compound and tests the activity of the compound for inhibiting falcipain-2 in experiment of enzyme level in vitro, and the result indicates that the compound has strong inhibitory activity to falcipain- 2. Therefore, the N-(4-substiguted aminoacyl phenyl)-5-substited furan-2-formamide compound provided in the invention can act as cysteine protease (falcipain-2) inhibitor in food vacuole of plasmodium to stop further proliferation of plasmodium in a host.

Description

technical field [0001] The present invention relates to an amide derivative and its use, in particular to an N-(4-substituted aminoacylphenyl)-5-substituted furan-2-carboxamide compound and its use. Background technique [0002] Malaria, the most frequent parasitic disease on Earth, is a potentially fatal disease transmitted by Anopheles mosquitoes. With the continuous increase of drug resistance to existing antimalarial drugs, the incidence of malaria is increasing, and the discovery of new antimalarial drugs with therapeutic effects is urgently needed. [0003] Plasmodium in the erythrocytic stage hydrolyzes the host's hemoglobin in its acidic food vacuole to obtain the energy and amino acids needed for its own life. Biological studies have shown that the food vesicles of Plasmodium contain a series of hydrolytic enzymes, such as plasmepsins, falcipains, and falcilysins. These enzymes have emerged as potential targets for malaria chemotherapy. [0004] Cysteine ​​protea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C07D307/68A61K31/341A61K31/506A61P33/02
CPCY02A50/30
Inventor 蒋华良李洪林李剑黄瑾朱进陈曈车鹏刘彦青卢伟强陈莉莉沈旭洛夫希金弗
Owner EAST CHINA UNIV OF SCI & TECH
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