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C-10 site carbamido substituted artemisinin derivative, preparation method and application

A kind of derivative, the technology of dihydroartemisinin, applied in the field of medicinal compound and its preparation, can solve the problem of low activity and the like

Inactive Publication Date: 2013-07-03
SHENYANG PHARMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Beekman et al. tested 60 tumor cell lines cultured from 9 different tissues and found that dihydroartemisinin was highly sensitive to leukemia, melanoma, colon cancer, prostate cancer and breast cancer cell lines, while non-small cell lung cancer, Less activity in central nervous system tumors, ovarian and kidney cancer cell lines

Method used

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  • C-10 site carbamido substituted artemisinin derivative, preparation method and application
  • C-10 site carbamido substituted artemisinin derivative, preparation method and application
  • C-10 site carbamido substituted artemisinin derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0157] Experimental example 1: 1-{2-[ (10 R Preparation of )-dihydroartemisinin-10-oxyl]ethyl}-3-(2-methylphenyl)urea

[0158]

[0159] In a 250 ml reaction vial, 4.26 g (15 mmol) of dihydroartemisinin and 3.12 g (15 mmol) of 1-(2-hydroxyethyl)-3-(2-methylphenyl)urea were dissolved in 200 ml In dry dichloromethane, cool to 0°C, add 1mL Et dropwise under stirring 2 O·BF 3 , continued the reaction at 0°C for 8 hours, and monitored the end point of the reaction by TLC to obtain 1-{2-[(10 R )-Dihydroartemisinin-10-oxyl]ethyl}-3-(2-methylphenyl)urea in dichloromethane, with saturated NaHCO 3 solution to quench the reaction, respectively, with saturated NaHCO 3 solution (50 ml×5) and water (50 ml×5) to wash the reaction solution to neutrality, separate the organic layer, and wash with anhydrous Na 2 SO 4 Dry, filter off the desiccant, and distill off the dichloromethane under reduced pressure to obtain the crude product, which is purified by column chromatography (200-300...

experiment example 2

[0160] Experimental example 2: 1-{2-[ (10 R Preparation of )-dihydroartemisinin-10-oxyl]ethyl}-3-(3-chloro-2-methylphenyl)urea

[0161]

[0162] In a 250 ml reaction vial, 4.26 g (15 mmol) of dihydroartemisinin and 3.43 g (15 mmol) of 1-(2-hydroxyethyl)-3-(3-chloro-2-methylphenyl)urea Dissolve in 200 ml of dry dichloromethane, cool to 0°C, add 1 mL of Et dropwise under stirring 2 O·BF 3 , continued the reaction at 0°C for 8 hours, and monitored the end point of the reaction by TLC to obtain 1-{2-[(10 R )-Dihydroartemisinin-10-oxyl]ethyl}-3-(3-chloro-2-methylphenyl)urea in dichloromethane solution with saturated NaHCO 3 solution to quench the reaction, respectively, with saturated NaHCO 3 solution (50 ml×5) and water (50 ml×5) to wash the reaction solution to neutrality, separate the organic layer, and wash with anhydrous Na 2 SO 4 Dry, filter off the desiccant, and distill off the dichloromethane under reduced pressure to obtain the crude product, which is purified ...

experiment example 3

[0164] Experimental example 3: 1-{2-[ (10 R Preparation of )-dihydroartemisinin-10-oxyl]ethyl}-3-phenylurea

[0165]

[0166] In a 250 ml reaction vial, 4.26 g (15 mmol) of dihydroartemisinin and 2.7 g (15 mmol) of 1-(2-hydroxyethyl)-3-phenylurea were dissolved in 200 ml of dry dichloromethane , cooled to 0°C, 1mL Et was added dropwise with stirring 2 O·BF 3 , continued the reaction at 0°C for 8 hours, and monitored the end point of the reaction by TLC to obtain 1-{2-[(10 R )-dihydroartemisinin-10-oxyl]ethyl}-3-phenylurea in dichloromethane, saturated NaHCO 3 solution to quench the reaction, respectively, with saturated NaHCO 3 solution (50 ml×5) and water (50 ml×5) to wash the reaction solution to neutrality, separate the organic layer, and wash with anhydrous Na 2 SO 4 Dry, filter off the desiccant, and distill off dichloromethane under reduced pressure to obtain the crude product, which is purified by column chromatography (200-300 mesh silica gel, petroleum ethe...

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PUM

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Abstract

The invention relates to a C-10 site carbamido substituted artemisinin derivative (I), and relates to a structure, a preparation method and an application of the novel artemisinin 10 site derivative. The structural formula is shown as a formula I, and relates to its pharmaceutically acceptable salt, a solvate, an optical isomer or a polymorphic substance and a pharmaceutical composition which takes the compound as an active component. Being as a new antimalarial agent, an antitumor agent and an antifungal agent, the compound can be used for treating or preventing malaria, fungal infection, malignant tumor and the like. The compound takes substituted carbamide as an initial raw material, and is obtained by reacting with dihydroartemisinin under catalysis of Et2O.BF3.

Description

technical field [0001] The invention relates to a medicinal compound and its preparation method and application, in particular to a new class of artemisinin derivatives and its preparation method and application. The present invention also relates to the use of such compounds and their solvates, optical isomers or polymorphs as active ingredients in the preparation for treating / or preventing various tumor diseases and fungal diseases. Background technique [0002] Cancer is a disease that seriously threatens human life. With the deepening of research on the mechanism of tumorigenesis, the molecular mechanism of cancer development has been continuously revealed. [0003] Artemisinin is a sesquiterpene lactone containing peroxy groups extracted from the stems and leaves of Artemisia annua, Artemisia annua and its derivatives such as dihydroartemisinin, artemisinin The efficacy and characteristics of the antimalarial effects of ether, artether, artesunate, etc. have been affir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20A61K31/357A61P33/06A61P35/00A61P31/10
CPCY02A50/30
Inventor 郭春骆伟孙历李文昭丛琳田野张卫军苏昕夏明钰
Owner SHENYANG PHARMA UNIVERSITY
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