Arctigenin isoleucinate hydrochloride

An amino and mouse technology, applied in organic chemistry, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problems of low oral bioavailability and restricted application

Inactive Publication Date: 2018-04-24
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. ), the main active ingredient of the dried ripe fruit Arctium Fructus, 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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  • Arctigenin isoleucinate hydrochloride
  • Arctigenin isoleucinate hydrochloride
  • Arctigenin isoleucinate hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 14-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol 3-methyl-2-amino-valerate hydrochloride synthesis

[0013] Weigh 0.20g (0.54mmol) arctigenin, 0.25g (1.08mmol) Boc-L-isoleucine, 0.21g (1.08mmol) 1-ethyl-(3-dimethylaminopropyl) carbon Put diimine 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 then react at room temperature for 1-2 hours , TLC detected the reaction until the reaction was completed, 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 (acc...

Embodiment 2

[0014] Example 2 Arctigenin and 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol 3-methyl-2-amino-pentyl Solubility of ester hydrochloride in water

[0015]

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

Embodiment 3

[0017] Example 34-(4-(3,4-dimethoxybenzyl)-2-carbonyl)tetrahydrofuranmethyl-2-methoxyphenol 3-methyl-2-amino-valerate hydrochloride Inhibition of Tumor and Immunity Function of H22 Transplanted Tumor 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 19-21g, 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 isoleucine 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 In...

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Abstract

The invention provides 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl) tetrahydrofuran methyl-2-methoxyphenol-3-methyl-2-amino-pentanoate hydrochloride with a structural formula shown as formula I, applicableto an antineoplastic purpose, belonging to the field of researches on antineoplastic drugs. Experimental results show that the 4-(4-(3,4-dimethoxybenzyl)-2-carbonyl) tetrahydrofuran methyl-2-methoxyphenol-3-methyl-2-amino-pentanoate hydrochloride can take an obvious inhibitory effect on H22 transplanted tumor mice, so that immune organs of a body can be protected and immunologic functions of the body can be enhanced (Formula).

Description

technical field [0001] The invention relates to the application of arctigenin isoleucine 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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IPC IPC(8): A61K31/341A61P35/00C07D307/28
CPCA61K31/341C07D307/28
Inventor 蔡恩博赵岩宋星卓
Owner JILIN AGRICULTURAL UNIV
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