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Artemisinin derivative, synthesis method and applications thereof

A synthesis method and reaction technology, applied in the field of medicine, can solve problems such as undiscovered and achieve good medicinal value

Active Publication Date: 2016-03-23
GUILIN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no related report on N-(3-N’,N’-dimethylamino-propyl)-10-azadeoxyartemisinin

Method used

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  • Artemisinin derivative, synthesis method and applications thereof
  • Artemisinin derivative, synthesis method and applications thereof
  • Artemisinin derivative, synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) Take 410mg (1.44mmol) of artemisinin and 30ml of methanol in a 100ml round bottom flask, stir for 5 minutes under ice bath, add 423mg (2.88mmol) of N,N-dimethyl-1,3-di Aminopropane, under the protection of nitrogen, react at 0°C for 24 hours, evaporate the solvent to dryness after the reaction, and collect the residue;

[0025] 2) Dissolve the residue collected in the previous step in 30ml of dichloromethane, then add 550mg (2.88mmol) p-toluenesulfonic acid, react at room temperature, follow the reaction with TLC, and evaporate the solvent after the reaction is completed (about 40 hours) , extracted three times with 5w / w% sodium bicarbonate solution, then extracted with water, collected the organic phase, dried with anhydrous sodium sulfate and evaporated to dryness to obtain an oily substance;

[0026] 3) The oil obtained in the previous step was purified by silica gel column chromatography (eluting solvent: petroleum ether: dichloromethane = 1:1, volume ratio) to o...

Embodiment 2

[0035] 1) Take 410mg (1.44mmol) of artemisinin, 15ml of ethanol and 15ml of dichloromethane in a 100ml round bottom flask, stir for 5 minutes under ice bath, add 211mg (1.44mmol) of N,N-dimethyl- 1,3-diaminopropane, under the protection of nitrogen, react at 0°C for 24 hours, evaporate the solvent to dryness after the reaction, and collect the residue;

[0036] 2) Dissolve the residue collected in the previous step in 20ml of dichloromethane, add 275mg (1.44mmol) p-toluenesulfonic acid, react at room temperature, track the reaction with TLC, and use 5w / w% Sodium carbonate solution was extracted three times, and then extracted with water, the organic phase was collected, dried with anhydrous sodium sulfate, and evaporated to dryness to obtain an oily substance;

[0037] 3) The oil obtained in the previous step was purified by silica gel column chromatography (eluting solvent: petroleum ether: dichloromethane = 1:2, volume ratio) to obtain the target product (60 mg, yield 11.9%)...

Embodiment 3

[0039]1) Take 410mg (1.44mmol) of artemisinin, 5ml of n-butanol, 5ml of hexanol and 15ml of chloroform in a 100ml round bottom flask, stir for 5 minutes under ice bath, add 634mg (4.32mmol) of N,N-di Methyl-1,3-diaminopropane, under the protection of nitrogen, react at 0°C for 18 hours, evaporate the solvent to dryness after the reaction, and collect the residue;

[0040] 2) Dissolve the residue collected in the previous step in 40ml of chloroform, add 825mg (4.32mmol) p-toluenesulfonic acid, react at room temperature, track the reaction with TLC, extract three times with ammonia water after the reaction is completed (about 30 hours), and then water Extraction, collecting the organic phase, drying with anhydrous sodium sulfate and evaporating the solvent to obtain an oil;

[0041] 3) The oil obtained in the previous step was purified by silica gel column chromatography (eluting solvent: petroleum ether:dichloromethane=1:0.5, volume ratio) to obtain the target product (120 mg, ...

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Abstract

The invention discloses an artemisinin derivative, a synthesis method and applications thereof. The artemisinin derivate is N-(3-N',N'-dimethylamino-propyl)-10-azadeoxyartemisinin, which is prepared by reacting artemisinin with N,N-dimethyl-1,3-diaminopropane and p-toluene sulfonic acid in sequence. By researching the proliferation inhibition activity of the derivative on multiple human tumor cell strains and human normal cell strains, the applicant finds that the derivative has a prominent proliferation inhibition activity on human bladder cancer cell T-24, human ovarian cancer cell SK-OV-3, and human stomach cancer cell MGC80-3, has a potential medicinal value, and can be used to prepare various antitumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an artemisinin derivative and its synthesis method and application. Background technique [0002] Artemisinin is a semiterpene lactone compound obtained from the traditional Chinese medicine Artemisia annua (ie Artemisia annua). As early as 340 BC, Ge Hong of the Eastern Jin Dynasty described the antipyretic function of Artemisia annua for the first time in his book "Elbow Backing Emergency Prescription" written by him. Li Shizhen's "Compendium of Materia Medica" said that it can "cure malaria Cold and heat". Chinese scientist Tu Youyou obtained inspiration from classical literature, and used ether to separate the monomer from Artemisia annua at a temperature not exceeding 60°C, and named it artemisinin. Experiments have found that artemisinin has a 100% inhibition rate against Plasmodium malaria in mice and monkeys. In 1986, artemisinin obtained a new drug certificate. Acco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/20A61K31/4355A61P35/00
CPCC07D491/20
Inventor 郑清四彭艳张国海卢幸吴亦明杨阳
Owner GUILIN PHARMA
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