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Artemisinin-coumarin heterozygous molecule, method for preparing same and application of artemisinin-coumarin heterozygous molecule

A technology of dihydroartemisinin and halogen, applied in the directions of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc., can solve the problems of poor water solubility, low bioavailability, and limited clinical application.

Active Publication Date: 2016-12-07
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, natural coumarin often has defects such as unsatisfactory activity, poor water solubility, or low bioavailability, which limits its clinical application.

Method used

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  • Artemisinin-coumarin heterozygous molecule, method for preparing same and application of artemisinin-coumarin heterozygous molecule
  • Artemisinin-coumarin heterozygous molecule, method for preparing same and application of artemisinin-coumarin heterozygous molecule
  • Artemisinin-coumarin heterozygous molecule, method for preparing same and application of artemisinin-coumarin heterozygous molecule

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0058] Experimental example 1: Preparation of 7-{[(10S)-dihydroartemisinin-10-oxyl]}-4-methyl-2H-benzothiopyran-2-one (TY-1)

[0059]

[0060] Add 2.8g (0.01mol) of dihydroartemisinin and 1.01g (0.01mol) of triethylamine into a 100mL reaction flask, add 30mL of dry dichloromethane, stir to dissolve, cool to -5°C, and drop Add 1.4mL (0.01mol) trifluoroacetic anhydride, after dropping, continue to react at 0°C for 8 hours to obtain a dichloromethane solution of 10-trifluoroacetoxydihydroartemisinin, which can be used directly for Next reaction. 1.8 g (0.01 mol) of 7-hydroxy-4-methylcoumarin was added to the solution prepared above, and the stirring reaction was continued at room temperature for 24 h after the addition was completed (monitored by TLC at the end of the reaction). Add 30 mL of dichloromethane to the reaction solution, separate the organic layer, and wash with saturated sodium bicarbonate solution 5 times (5 × 20 mL), dry the organic phase with anhydrous sodium ...

experiment example 2

[0061] Experimental example 2: Preparation of 7-{[(10S)-dihydroartemisinin-10-oxyl]}-4-trifluoromethyl-2H-benzothiopyran-2-one (TY-2)

[0062]

[0063] Add 2.8g (0.01mol) of dihydroartemisinin and 1.01g (0.01mol) of triethylamine into a 100mL reaction flask, add 30mL of dry dichloromethane, stir to dissolve, cool to -5°C, and drop Add 1.4mL (0.01mol) of trifluoroacetic anhydride, after dropping, continue to stir and react at 0°C for 8 hours to obtain a dichloromethane solution of 10-trifluoroacetoxydihydroartemisinin, without further treatment, directly use react in the next step. 2.3 g (0.01 mol) of 7-hydroxy-4-trifluoromethylcoumarin was added to the solution prepared above, and the stirring reaction was continued at room temperature for 14 hours after the addition was completed (the end point of the reaction was monitored by TLC). Add 30 mL of dichloromethane to the reaction solution, separate the organic layer, and wash with saturated sodium bicarbonate solution 5 time...

experiment example 3

[0064] Experimental example 3: Preparation of 7-{[(10S)-dihydroartemisinin-10-oxyl]}-4-nitro-2H-benzothiopyran-2-one (TY-3)

[0065]

[0066] Add 2.8g (0.01mol) of dihydroartemisinin and 1.01g (0.01mol) of triethylamine into a 100mL reaction flask, add 30mL of dry dichloromethane, stir to dissolve, cool to -5°C, and drop Add 1.4mL (0.01mol) of trifluoroacetic anhydride, after dropping, continue to stir and react at 0°C for 8 hours to obtain a dichloromethane solution of 10-trifluoroacetoxydihydroartemisinin, without further treatment, directly use react in the next step. 2.1 g (0.01 mol) of 7-hydroxy-4-nitrocoumarin was added to the solution prepared above, and the stirring reaction was continued at room temperature for 5 hours after the addition was completed (the end of the reaction was monitored by TLC). Add 30 mL of dichloromethane to the reaction solution, separate the organic layer, and wash with saturated sodium bicarbonate solution 5 times (5 × 20 mL), dry the orga...

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Abstract

The invention aims to provide an artemisinin-coumarin heterozygous molecule, a method for preparing the same and application of the artemisinin-coumarin heterozygous molecule, provides pharmaceutically acceptable salt, solvate, an optical isomer or a polymorphic substance of the artemisinin-coumarin heterozygous molecule and further provides a medicine with a derivative or salt of the derivative. The derivative or the salt of the derivative is an active ingredient of the medicine. Structural formulas of compounds or the pharmaceutically acceptable salt, the solvate, the optical isomer or the polymorphic substance are shown as a formula (I), wherein an L in the formula represents O, O(CH<2>)<n>O, the n is equal to 0-3, and an R1 and an R2 in the formula independently represent hydrogen atoms, halogen, hydroxyl, C1-C10 carboxyl, C1-C10 ester, cyan, nitro, C1-C10 alkyl, C1-C10 alkoxy, C3-C7 naphthene, halogenated C1-C10 alkyl and halogenated C1-C10 alkoxy.

Description

technical field [0001] The invention relates to a medicinal compound, its preparation method and its application in antitumor, in particular to a new class of artemisinin-coumarin hybrid molecules, its preparation method and application. Background technique [0002] "Molecular hybridization" refers to the design of multi-target drugs or drugs with synergistic effects on the basis of the original single-target drug. The main types include: combining two types of drugs (or chemical structures) with different mechanisms of action A new molecule (drug) connected by a linking group hydrolyzed by a specific enzyme, which can form two types of drugs that bind to different targets after being hydrolyzed by an enzyme in the body to exert a synergistic pharmacological effect, also known as a synergistic prodrug; One type is: the binding mode is similar to the synergistic prodrug, but the linking group is stable and not easily hydrolyzed by enzymes. The two types of chemical structure...

Claims

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Application Information

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IPC IPC(8): C07D493/20A61K31/37A61P35/00A61P35/02
CPCC07D493/20
Inventor 郭春田野候壮郭梦笔李见腾牟艳华夏明钰
Owner SHENYANG PHARMA UNIVERSITY
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