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Ligustrazine acylhydrazone derivatives, and preparation method and application thereof

A technology of ligustrazine acyl hydrazone and ligustrazine hydrazide is applied in the field of ligustrazine acyl hydrazone derivatives, which can solve the problems of high normal cytotoxicity, low yield, low antitumor activity and the like, and achieves low normal cytotoxicity, Simple synthetic route and strong antitumor activity

Active Publication Date: 2017-09-01
WEIFANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, when preparing ligustrazine acylhydrazone derivatives, there are defects of low yield, low antitumor activity and high toxicity to normal cells

Method used

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  • Ligustrazine acylhydrazone derivatives, and preparation method and application thereof
  • Ligustrazine acylhydrazone derivatives, and preparation method and application thereof
  • Ligustrazine acylhydrazone derivatives, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Example 1 A preparation method of ligustrazine acylhydrazone derivatives

[0046] Include the following steps:

[0047] (1) Preparation of Ligustrazinic Acid

[0048] 8.4% KMnO 4 Aqueous solution (contains KMnO 4 6.32g) was added dropwise to 3.8g ligustrazine, and the dropwise addition was completed within 60 minutes. The reaction temperature was controlled at 35°C, reacted for 24 hours, filtered, the filtrate was concentrated under reduced pressure, cooled in an ice-water bath, adjusted to pH 1 with dilute hydrochloric acid, and kept in the refrigerator overnight Refrigerate, extract with chloroform, concentrate under reduced pressure, and then recrystallize with 95% ethanol to obtain ligustrazinic acid as a light yellow crystalline powder.

[0049] (2) Preparation of Ethyl Ligustrazinate

[0050] Add 0.75mL (0.0138mol) of concentrated sulfuric acid to 1.66g (0.01mol) of ligustracinic acid and 17mL of absolute ethanol (0.29mol), and reflux for 24h. Concentrate und...

Embodiment 2

[0056] Embodiment 2 A kind of preparation method of ligustrazine acylhydrazone derivatives

[0057] Include the following steps:

[0058] (1) Preparation of Ligustrazinic Acid

[0059] Will contain 8.4% KMnO 4 Aqueous solution (contains KMnO 4 63.2g) was added dropwise to 38g ligustrazine, and the dropwise addition was completed within 60 minutes. The reaction temperature was controlled at 35°C, reacted for 24 hours, filtered, the filtrate was concentrated under reduced pressure, cooled in an ice-water bath, adjusted to pH 1 with dilute hydrochloric acid, and refrigerated overnight , extracted with chloroform, concentrated under reduced pressure, and then recrystallized with 95% ethanol to obtain ligustrazinic acid as a pale yellow crystalline powder.

[0060] (2) Preparation of Ethyl Ligustrazinate

[0061] Add 1.5mL (0.0276mol) of concentrated sulfuric acid to 16.6g (0.1mol) of ligustracinic acid and 170mL (2.9mol) of absolute ethanol, and reflux for 16h. Concentrate un...

Embodiment 3

[0067] Embodiment 3 A kind of preparation method of ligustrazine acylhydrazone derivatives

[0068] Include the following steps:

[0069] (1) Preparation of Ligustrazinic Acid

[0070] Will contain 8.4% KMnO 4 Aqueous solution (contains KMnO 4 3.16g) was added dropwise to 19g ligustrazine, and the dropwise addition was completed within 60 minutes. The reaction temperature was controlled at 35°C, reacted for 24 hours, filtered, the filtrate was concentrated under reduced pressure, cooled in an ice-water bath, adjusted to pH 1 with dilute hydrochloric acid, and refrigerated overnight , extracted with chloroform, concentrated under reduced pressure, and then recrystallized with 95% ethanol to obtain ligustrazinic acid as a pale yellow crystalline powder.

[0071] (2) Preparation of Ethyl Ligustrazinate

[0072] Add 0.86mL (0.0158mol) of concentrated sulfuric acid to 8.2g (0.049mol) of ligustracinic acid and 83mL of absolute ethanol (1.42mol), and reflux for 16h. Concentrate ...

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Abstract

The invention discloses a preparation method and application of ligustrazine acylhydrazone derivatives. The structural formula of the ligustrazine acylhydrazone derivatives is as shown in the description; and the chemical name of the ligustrazine acylhydrazone derivatives is N-(2-hydroxybenzmethylene)-3,5,6-trimethyl pyrazine-2-formylhydrazine, the molecular formula is C15H16N4O2, and the relative molecular weight is 284.13. The preparation method of the ligustrazine acylhydrazone derivatives is simple, convenient and high in yield. The ligustrazine acylhydrazone derivatives have anti-tumor effect, have low toxicity on normal cells, and may become a novel, efficient and low-toxicity anti-tumor medicine.

Description

technical field [0001] The invention relates to a ligustrazinyl hydrazone derivative with antitumor activity, a preparation method and an application thereof, belonging to the field of chemical medicine. Background technique [0002] Cancer seriously affects human health and life safety, and the development and application of antitumor drugs is an important way to solve this problem. Ligustrazine is the main active ingredient of the traditional Chinese medicine Ligusticum Chuanxiong, which has the functions of anti-platelet aggregation and dilating blood vessels. It is mainly used clinically for the treatment of ischemic cardiovascular and cerebrovascular diseases. In recent years, studies have found that ligustrazine and its derivatives can inhibit the growth, invasion and metastasis of lung cancer by improving the hypercoagulable state of tumor-bearing organisms and inducing the apoptosis pathway of tumor cells. Ligustrazine and its derivatives show good application prosp...

Claims

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Application Information

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IPC IPC(8): C07D241/24A61P35/00
CPCC07D241/24
Inventor 刘冬梅盛继文张维芬
Owner WEIFANG MEDICAL UNIV
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