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Method for preparing Artemisin G

A technology for artemisinin and raw materials, applied in the field of preparing ArtemisininG, can solve the problems of unsuitability for industrial production, cumbersome processing steps, large dosage, etc., and achieves the effects of easy handling, concise synthesis route, and simple reaction operation.

Active Publication Date: 2021-12-03
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the commonly used methods for synthesizing Artemisinin G include dissolving artemisinin in acetonitrile, adding FeCl 2 4H 2 O reaction can reach a higher yield (78%) ( Helv. Chim. Acta 1996, 79 , 1475-1487), but FeCl 2 4H 2 The amount of O is relatively large (1 equivalent), the subsequent processing steps are cumbersome, and the by-product is similar in nature to Artemisinin G, which is difficult to separate through simple steps, making it unsuitable for industrial production

Method used

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  • Method for preparing Artemisin G
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Experimental program
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Effect test

Embodiment 1

[0018]

[0019] Mix 3 mL of acetonitrile and 0.6 mL of chloroform, add artemisinin (0.282 g, 1 mmol) and TBADT (13.6 mg, 0.005 mmol) at room temperature. The reaction system was an argon atmosphere, and it was placed at room temperature and reacted under 370 nm light for half an hour. The solvent was then removed to obtain a crude product, which was purified by silica gel column chromatography (PE / EtOAc = 4:1, volume ratio) to obtain a white solid (0.259 g, reaction yield 92%).

[0020] Physical state: white powdery solid;

[0021] Melting point: 91-93℃;

[0022] 1 H NMR (400 MHz, CDCl 3 ) δ 6.65 (1H, s), 4.21 (1H, t, J = 7.6 Hz), 3.94(1H, dd, J = 7.4, 15.8 Hz), 3.16 (1H, dq, J = 2.7, 7.2 Hz), 2.16 (3H, s), 1.8-2.1 (4H, m), 1.73 (1H, m), 1.60 (1H, m), 1,47 (1H, m), 1.21 (3H, d, J =7.3 Hz), 1.08 (1H, m), 0.99 (3H, d, J = 6.3 Hz).

[0023] 13 C NMR (90 MHz, CDCl 3 ) δ 12.4, 20.3, 21.1, 24.2, 27.6, 30.8, 34.6, 34.9, 46.6, 54.8, 69.1, 79.3, 92.9, 168.3, 171.5. ...

Embodiment 2

[0026] Mix 15 mL of acetonitrile and 3 mL of chloroform, add artemisinin (1.41 g, 5 mmol) and TBADT (68 mg, 0.025 mmol) at room temperature. The reaction system was filled with argon, and placed at room temperature under 370 nm light for half an hour to react. The solvent was then removed to obtain a crude product, which was purified by silica gel column chromatography (PE / EtOAc = 4:1, volume ratio) to obtain a white solid (1.33 g, 94%).

Embodiment 3

[0028] Mix 150 mL of acetonitrile and 30 mL of chloroform, add artemisinin (14.1 g, 50 mmol) and TBADT (680 mg, 0.25 mmol) at room temperature. The reaction system was filled with argon, and placed at room temperature under 370 nm light for half an hour to react. The solvent was then removed to obtain a crude product, which was purified by silica gel column chromatography (PE / EtOAc = 4:1, volume ratio) to obtain a white solid (12.8 g, 91%).

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Abstract

The invention belongs to the technical field of medicines, and provides a method for preparing Artemisin G. According to the method, artemisinin is taken as an initial raw material, and Artemisinin G is synthesized through a one-step reaction. Reagents used for synthesis are commonly used reagents in laboratories, and the reaction can be rapidly completed at room temperature. In conclusion, the needed materials are easy to obtain, the cost is low, the reaction operation is simple, the reaction time is short, the reaction liquid is easy to treat, and a large amount of Artemisinin G can be obtained and used for medicine research and development.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a method for preparing Artemisinin G. Background technique [0002] Artemisinin and its derivatives are often used in the development of anti-malarial drugs, and artemisinin-based combination therapy is also the most effective and important means of treating malaria. In recent years, with the deepening of research, more and more other effects of artemisinin drugs have been discovered and applied research, such as anti-tumor, treatment of pulmonary hypertension, anti-diabetes, anti-fungal, immune regulation, anti-virus, anti- Pulmonary fibrosis, cardiovascular effects and other pharmacological effects. Li et al. extracted another active substance Artemisinin G ( Planta Med, 1992, 58 ). Artemisinin G can be obtained after biological metabolism of artemisinin in the body. Artemisinin G does not contain the characteristic peroxygen bridge of artemisinin, so it is speculated th...

Claims

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Application Information

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IPC IPC(8): C07D493/10
CPCC07D493/10Y02A50/30
Inventor 陈海军罗伊宁张宇彤高瑜
Owner FUZHOU UNIV
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