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Application of arctigenin valine ester hydrochloride to preparation of anti-tumor drugs

The technology of methyl butyrate and application is applied in the application field of arctigenin valine ester hydrochloride in the preparation of antitumor drugs, and can solve the problems of low oral bioavailability, restricted application and the like

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

[0004] Arctigenin, a lignanolactone compound, is a member of the Compositae plant Burdock ( Arctium Iappa L.) is the main active ingredient of the dried ripe fruit Arctium Fructus, and the prior art has disclosed the use of arctigenin for antitumor, but its oral bioavailability is low, which seriously restricts its clinical application

Method used

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  • Application of arctigenin valine ester hydrochloride to preparation of anti-tumor drugs
  • Application of arctigenin valine ester hydrochloride to preparation of anti-tumor drugs
  • Application of arctigenin valine ester hydrochloride to preparation of anti-tumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol 2-amino-3-methylbutyrate hydrochloride synthesis.

[0013] Weigh 0.20g (0.54mmol) arctigenin, 0.23g (1.08mmol) Boc-L-valine, 0.21g (1.08mmol) 1-ethyl-(3-dimethylaminopropyl) carbon diacetate Put imine 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 1-2 hours. The reaction was detected by TLC until the reaction was complete, and the solvent was evaporated 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 above...

Embodiment 2

[0014] Example 2 Arctigenin and 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol 2-amino-3-methylbutanoic acid The solubility of ester 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-3-methylbutyrate hydrochloride is greatly increased, which improves the shortcoming of arctigenin's low solubility and helps to improve the bioavailability.

Embodiment 3

[0017] Example 3 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol 2-amino-3-methylbutyrate hydrochloride Tumor suppression and immune function in 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 valine ester 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 Bioengineering Institute...

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Abstract

The invention provides a 4-(4-(3, 4-dimethoxy benzene methyl)-2-carbonyl) tetrahydrofurfuryl-2-methoxyphenol 2-amino-3-methyl butyric acid ester hydrochloride for resisting tumors, and belongs to the field of research of anti-tumor drugs. Experimental results indicate that the 4-(4-(3, 4-dimethoxy benzene methyl)-2-carbonyl) tetrahydrofurfuryl-2-methoxyphenol 2-amino-3-methyl butyric acid ester hydrochloride has obvious inhibition effect on hepatocarcinoma 22 solid tumor-bearing mice, immune organs of organisms can be protected to some extent, and immune functions of the organisms are enhanced.

Description

technical field [0001] The invention relates to the application of arctigenin valine ester 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 priori...

Claims

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Application Information

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IPC IPC(8): A61K31/365C07D307/33A61P35/00
CPCA61K31/365C07D307/33
Inventor 蔡恩博杨利民赵岩
Owner JILIN AGRICULTURAL UNIV
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