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Bromodihydroartemisinin and preparation method thereof

A dihydroartemisinin, brominated technology, applied in the field of chemistry, can solve the problems of limited application, toxic and side effects of chemical drugs, large toxic and side effects, etc.

Active Publication Date: 2007-10-17
SICHUAN KELUN PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemical drugs are quite effective in killing tumor cells, but they have serious limitations: 1. Too many toxic and side effects. Many cancer patients do not die from tumors, but from the toxic and side effects of chemical drugs
2. High drug resistance
But its drug effect is still not as strong as chemical drugs such as doxorubicin, which is used in a larger amount on the market, which limits its clinical application.

Method used

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  • Bromodihydroartemisinin and preparation method thereof
  • Bromodihydroartemisinin and preparation method thereof
  • Bromodihydroartemisinin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Mix 9g of dihydroartemisinin and 300ml of acetonitrile, and introduce 2ml of bromine water at a temperature of 40°C. The bromine water conduit should go deep into the bottom of the reactant while stirring so that the reactant can fully contact with bromine water. After 50 minutes, pour into Add 9ml of 10% sodium thiosulfate solution to the reaction mixture, collect the organic phase, then add 60ml of 10% sodium bicarbonate solution, add ethyl acetate to collect the organic layer, and dehydrate the organic layer with anhydrous sodium sulfate and concentrate under reduced pressure to obtain Crystallized and dried to obtain brominated dihydroartemisinin as yellowish block crystals, which were recrystallized with n-hexane to obtain white needle crystals.

[0023] IRv KBr max : 1745, 1115, 831, 881cm -1 . The infrared spectrum of brominated dihydroartemisinin is shown in Figure 3. Compared with the infrared spectrum of dihydroartemisinin, there are more bromine peaks such...

Embodiment 2

[0114] 1.5g of dihydroartemisinin and 50ml of dimethylformamide were mixed, and 0.3ml of bromine was introduced at 25°C. After 5 minutes, 15ml of 10% sodium thiosulfate solution was added to the reaction mixture, and the organic phase was collected. Then add 30ml of 10% sodium bicarbonate solution, add ethyl acetate to collect the organic layer, dehydrate the organic layer with anhydrous sodium sulfate and concentrate under reduced pressure to form crystals, wash the crystals with n-hexane, filter the crystals, and dry to obtain bromobis Hydrogenartemisinin is yellowish block crystal. Recrystallization with n-hexane gave white needle crystals.

Embodiment 3

[0116] Mix 1.5g of dihydroartemisinin and 50ml of acetic acid, add 0.3ml of bromine water at 0°C, stir and react for 200 minutes, add water and stir for debromination, collect the organic layer and concentrate under reduced pressure to form crystals, wash the crystals with n-hexane , filtered out the crystals, and dried to obtain brominated dihydroartemisinin. After drying, white needle-like crystals were obtained.

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Abstract

The present invention relates to bromodihydro arteannuin and also provides its preparation method which comprise the following steps: dissolving dihydro arteannuin in protecting solvent of bromination reaction, adding bromine or bromide under 0-40 degree, stirring 10-200min, filtering, washing with bromine removing solution, Collecting organic layer, dehydrating the organic layer, then vacuum concentrating of organic layer. using normal hexane for recrystallization, obtaining final product. In vitro anticancer test prove that bromodihydro arteannuin possess good anticancer effect.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to brominated dihydroartemisinin and a preparation method thereof. Background technique [0002] Malignant tumors are currently one of the most serious diseases that endanger people's lives and health. According to the statistics of the World Health Organization (WHO), there are about 10 million cancers in the world every year, and about 7 million deaths. Tumor is a systemic and complex systemic disease, and surgery and radiotherapy can only solve local problems. Chemical drugs have considerable effects in killing tumor cells, but they have serious limitations: 1. Too many toxic and side effects. Many cancer patients do not die from tumors, but from the toxic and side effects of chemical drugs. Second, high drug resistance. After several years of use, the efficacy of the drug decreases significantly. In order to achieve the original effect, the clinical dose has to be increased, resultin...

Claims

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Application Information

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IPC IPC(8): C07D493/18A61K31/357A61P35/00
CPCC07D493/18A61P35/00
Inventor 石雁羽程志鹏梁隆祝华军李明验
Owner SICHUAN KELUN PHARMA CO LTD