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Preparation method and application of arctigenin derivatives

A technology of arctigenin and its derivatives, which is applied in the field of preparation of arctigenin derivatives, can solve the problems of arctigenin anti-cancer new drug development difficulties, low bioavailability, and low water solubility, and achieve solvent-saving and preparation The effect of simple process and easy post-processing

Inactive Publication Date: 2015-04-22
LIAONING UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, arctigenin belongs to lignan compounds, which has low water solubility and low bioavailability, which brings certain difficulties to the development of new anticancer drugs for arctigenin.

Method used

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  • Preparation method and application of arctigenin derivatives
  • Preparation method and application of arctigenin derivatives
  • Preparation method and application of arctigenin derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0029] Add 74.8 mg arctigenin and 2 mL ethanolamine solution into a round bottom flask, stir at room temperature, and stop the reaction. The reaction liquid is concentrated under reduced pressure, and the residual liquid is separated by high-efficiency preparation liquid phase to obtain the ammonolysis derivative of arctigenin 1， Among them compounds 1 for new compounds.

[0030]

[0031] Measuring conditions: INSTROM AV500

[0032] Solvent: CDCl 3

[0033] Table 1 Compound 1 13 C-NMR and 1 H-NMR nuclear magnetic resonance data

[0034]

preparation example 2

[0036] 111.6mg of arctigenin was placed in a 25mL round bottom flask, 6.0mL of n-propylamine solution was added, stirred and dissolved at 25°C, and the reaction was stopped after 24 hours of reaction. The reaction solution was concentrated under reduced pressure and recrystallized from methanol to obtain the compound 2 , where the compound 2 for new compounds.

[0037]

[0038] Measuring conditions: INSTROM AV500

[0039] Solvent: CDCl 3

[0040] Table 2 Compound 2 13 C-NMR and 1 H-NMR nuclear magnetic resonance data

[0041]

preparation example 3

[0043] Add 96mg arctigenin and 1mL benzylamine solution into a round bottom flask, and react at 160°C for 12 hours. Cool the reaction solution to room temperature, add 10% dilute hydrochloric acid to the reaction solution, extract 3-5 times with ethyl acetate, combine the extracts, concentrate, and then use high-efficiency preparative liquid phase for separation to obtain the compound 3 .

[0044]

[0045] Measuring conditions: INSTROM AV500

[0046] Solvent: CDCl 3

[0047] Table 3 Compound 3 13 C-NMR and 1 H-NMR nuclear magnetic resonance data

[0048]

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Abstract

The method of the invention adopts arctigenin as a lead compound, carries out structure modification of arctigenin by chemical methods of demethylation, oxygen atom acylation, aminomethylation, ester aminolysis and hydrolysis, and the like, synthesizes 15 arctigenin structure derivatives, seven of which are new compounds. In the structural formula, R, R'=O or R=NHR'', R'=O or R=R'=OH, R1=OCH3 or H, R2=H or COCH3 or COC6H5 or COCH2CH2COOH, R3=H or CH2NR1'R2', R4=R5=H or SO3Na, R6=OCH3 or H, R7=OCH3 or H. The invention relates to the preparation process of the derivatives and research of the antineoplastic activity of the derivatives.

Description

technical field [0001] The invention relates to a preparation method and application of arctigenin derivatives. Background technique [0002] Arctium is a plant of the genus Arctium in the family Compositae (Compositae) Arctium lappa ) of the dried ripe fruit. Burdock Fructus has the effects of dispelling wind and cooling, clearing the lungs and clearing rash, detoxifying the throat, and clearing the intestines. disease. The main medicinal component of Arctium Fructus is arctiin. Our research results and foreign reports all indicate that arctiin exerts its medicinal effect by metabolizing into arctigenin in the gastrointestinal tract. However, arctigenin is a lignan compound with low water solubility and low bioavailability, which brings certain difficulties to the development of new anticancer drugs for arctigenin. Therefore, the present invention relates to the structural modification of the traditional Chinese medicine arctigenin as the lead compound and then the deve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C231/02C07D307/33C07C59/64C07C51/09A61P35/00
Inventor 窦德强陈桂荣康廷国
Owner LIAONING UNIV OF TRADITIONAL CHINESE MEDICINE
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