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A kind of artemisinin-piperazine-furanone derivative and its preparation method and application

A derivative, artemisinone technology, applied in the field of artemisinone-piperazine-furanone derivatives and its preparation, can solve the problems of poor therapeutic effect and high clinical recurrence rate, achieve simple operation and improve anti-tumor activity , the effect of inhibiting growth

Active Publication Date: 2021-08-03
NINGXIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For this reason, the embodiment of the present invention provides an artemisinin-piperazine-furanone derivative to solve the problem of high clinical recurrence rate and poor therapeutic effect caused by the easy decomposition of artemisinin and its derivatives in the prior art. question

Method used

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  • A kind of artemisinin-piperazine-furanone derivative and its preparation method and application
  • A kind of artemisinin-piperazine-furanone derivative and its preparation method and application
  • A kind of artemisinin-piperazine-furanone derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 1. Artemisinin-piperazine-furanone derivatives

[0056] The structural formula of the above-mentioned artemisinin-piperazine-furanone derivatives is shown in formula 1:

[0057]

[0058] 2. Preparation method

[0059] The preparation method of above-mentioned artemisinin-piperazine-furanone derivatives comprises the following steps:

[0060] (a) Artemisinone-piperazine and 3,4-dichloro-5-methoxyfuranone are dissolved in acetonitrile to obtain a mixture, wherein the molar ratio of artemisinone-piperazine to halogenated furanone is 1 : 1, the concentration of artesunate-piperazine in the mixture is 0.012mmol / mL;

[0061] (b) Diisopropylethylamine is added to the mixture, and the reaction is carried out under stirring conditions, wherein the molar ratio of diisopropylethylamine to artesunone-piperazine is 3: 1, and the reaction temperature is room temperature, The reaction time is 4h;

[0062] (c) After the reaction is completed, the solvent is evaporated, and the m...

Embodiment 2

[0070] 1. Artemisinin-piperazine-furanone derivatives

[0071] The structural formula of the above-mentioned artemisinin-piperazine-furanone derivatives is shown in formula 2:

[0072]

[0073] 2. Preparation method

[0074] The preparation method of the above artesunone-piperazine-furanone derivatives is basically the same as the preparation method in Example 1, the only difference is that 3,4-dichloro-5-menthyloxyfuranone is replaced by 3,4- Dichloro-5-methoxyfuranone.

[0075] Weigh the mass of artesunone-piperazine-furanone derivatives prepared above, and then calculate the weighed mass÷theoretical yield×100%, and the yield of the above preparation method is 82%.

[0076] The artesunone-piperazine-furanone derivatives prepared above were selected for nuclear magnetic resonance and mass spectrometry analysis; 1 H NMR spectrum, 13 C NMR spectrum and mass spectrogram as Figure 4-6 shown;

[0077] Depend on Figure 4-6 It can be seen that: 1 H NMR (CDCl 3 )δ5.78(d...

Embodiment 3

[0082] 1. Artemisinin-piperazine-furanone derivatives

[0083] The structural formula of the above-mentioned artemisinin-piperazine-furanone derivatives is shown in formula 3:

[0084]

[0085] 2. Preparation method

[0086] The preparation method of the above artesunone-piperazine-furanone derivatives is basically the same as the preparation method in Example 1, the only difference is that 3,4-dichloro-5-bornyloxyfuranone is replaced by 3,4- Dichloro-5-methoxyfuranone.

[0087] Weigh the mass of artesunone-piperazine-furanone derivatives prepared above, and then calculate the weighed mass÷theoretical yield×100%, and the yield of the above preparation method is 80%.

[0088] The artesunone-piperazine-furanone derivatives prepared above were selected for nuclear magnetic resonance and mass spectrometry analysis; 1 H NMR spectrum, 13 C NMR spectrum and mass spectrogram as Figure 7-9 shown;

[0089] Depend on Figure 7-9 It can be seen that: 1 H NMR (CDCl 3 )δ5.73(s,...

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Abstract

The embodiment of the present invention discloses an artesunone-piperazine-furanone derivative and its preparation method and application. The general formula of the derivative is as follows: wherein, R is or X is Br or Cl. Artemisinone-piperazine-furanone derivatives of the present invention form multiple hydrogen bonds or ionic bonds through the addition of piperazine to improve the biological activity of the derivatives, and adjust the solubility and acid-base balance of the derivatives to promote The pharmacokinetics of the derivative, and the addition of furanone can significantly improve the anti-tumor activity of the prepared derivative, so that the derivative can significantly inhibit the growth of tumor cells.

Description

technical field [0001] The embodiment of the present invention relates to the technical field of artemisinic sulfone derivatives, in particular to an artemisinic sulfone-piperazine-furanone derivative and its preparation method and application. Background technique [0002] Liver cancer is a malignant tumor of the liver, which can be divided into two categories: primary and secondary. Primary malignant tumors of the liver originate from the epithelial or mesenchymal tissues of the liver. The former is called primary liver cancer, which is a malignant tumor with a high incidence in China and is extremely harmful; rare. Secondary or metastatic liver cancer refers to malignant tumors originating from multiple organs throughout the body and invading the liver. Generally, it is more common in liver metastases of malignant tumors in stomach, biliary tract, pancreas, colorectum, ovary, uterus, lung, breast and other organs. [0003] Artemisinin and its derivatives (such as artes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/20A61K31/541A61P35/00
CPCA61P35/00C07D493/20
Inventor 魏梦雪于家瀛
Owner NINGXIA UNIVERSITY
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