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Application of fructus arctii aglycon methionine ester hydrochloride to preparation of antitumor medicine

A technology for the use of methylthiobutyrate, which is applied in the field of application of arctigenin methionine hydrochloride in the preparation of antitumor drugs, and can solve the problems of restricted application and low oral bioavailability

Inactive Publication Date: 2017-02-22
JILIN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art has disclosed the use of arctigenin for anti-tumor, but its oral bioavailability is low, which seriously restricts its clinical application

Method used

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  • Application of fructus arctii aglycon methionine ester hydrochloride to preparation of antitumor medicine
  • Application of fructus arctii aglycon methionine ester hydrochloride to preparation of antitumor medicine
  • Application of fructus arctii aglycon methionine ester hydrochloride to preparation of antitumor medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 14-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol-2-amino-4-methylthiobutyrate hydrochloride Synthesis.

[0013] Weigh 0.20g (0.54mmol) arctigenin, 0.27g (1.08mmol) Boc-L-methionine, 0.21g (1.08mmol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide Put hydrochloride (EDCI), 0.03g (0.27mmol) 4-dimethylaminopyridine (DMAP) in a 100ml spinner bottle, add 10ml of acetonitrile solution, stir and dissolve in an ice-water bath, and react at room temperature for 2 hours, and TLC detects that the reaction reaches After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a light yellow viscous substance. The viscous material was separated by column chromatography with YMC reverse-phase packing, and eluted with acetonitrile / water (55:45) mixed solvent to collect the desired components, recover the organic solvent, and freeze-dry to obtain a white powdery compound. Dissolve the white powdery compound obtained a...

Embodiment 2

[0014] Example 2 Arctigenin and 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol-2-amino-4-methylthio The solubility of butyrate hydrochloride in water is shown in Table 1.

[0015]

[0016] As can be seen from Table 1, after arctigenin is structurally modified, its modified product 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofurylmethyl-2-methoxy The water solubility of phenol-2-amino-4-methylthiobutyrate hydrochloride is greatly increased, which improves the shortcoming of arctigenin's low solubility and helps to improve the bioavailability.

Embodiment 3

[0017] Example 34-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol-2-amino-4-methylthiobutyrate hydrochloride Effects on the tumor suppressor effect and immune function of H22 xenografted mice.

[0018] 1. Materials and methods

[0019] 1.1 Materials

[0020] 1.1.1 Experimental animals and cell lines

[0021] SPF grade ICR mice (male), weighing 19-21 g, animal certificate number: SCXK (Ji)-2011-0004, were purchased from Changchun Yisi Experimental Animal Technology Co., Ltd. Mouse quality inspection unit: Jilin Provincial Laboratory Animal Quality Inspection Center.

[0022] 1.1.2 Drugs and reagents

[0023] Arctigenin extraction and separation preparation

[0024] Synthesis and preparation of arctigenin methionine hydrochloride

[0025] Cyclophosphamide (CTX) Shanghai Hualian Pharmaceutical Co., Ltd.

[0026] Burea Nitrogen (BUN) Test Kit Nanjing Jiancheng Bioengineering Research Institute

[0027] Creatinine (Cr) Test Kit Nanjing Jiancheng Bi...

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Abstract

The invention provides a 4-(4-(3,4-dimethoxy phenmethyl)-2-carbonyl) tetrahydrofurfuryl-2-methoxyphenol-2-amidogen-4-methylthio butyrate hydrochloride shown as a structural formula I, which is used for tumor resistance and belongs to the field of antitumor medicine study. Experimental results show that the 4-(4-(3,4-dimethoxy phenmethyl)-2-carbonyl) tetrahydrofurfuryl-2-methoxyphenol-2-amidogen-4-methylthio butyrate hydrochloride has an obvious inhibition effect on H22 transplantation tumor mice; the immune organs of a body can be protected to a certain degree; the immune function of the body is enhanced. The formula I is shown as the accompanying drawing.

Description

technical field [0001] The invention relates to the application of arctigenin methionine hydrochloride in the preparation of antitumor drugs. Background technique [0002] With the changes of human living environment, living standards and lifestyles and the advancement of medicine, the spectrum of diseases has undergone significant changes, general infectious diseases have been gradually controlled, and malignant tumors have become increasingly common and seriously threaten human life and quality of life. one of the major diseases. At present, in China and even in the world, cancer has become the second leading cause of human death. Malignant tumor is a disease in which the body's own cells become uncontrolled proliferation and spread, and it is a type of disease in which cell proliferation and differentiation are abnormal. Therefore, the World Health Organization and the health departments of governments of various countries have listed conquering cancer as a top priority...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365C07D307/33A61P35/00
CPCA61K31/365C07D307/33
Inventor 杨利民韩梅蔡恩博赵岩高小芮
Owner JILIN AGRICULTURAL UNIV
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