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Parthenolide dimer as well as salt, pharmaceutical composition and application thereof

A parthenolide and dimer technology, applied in the field of pharmacy, can solve the problems of water solubility, poor plasma stability, and low activity

Pending Publication Date: 2021-03-19
ACCENDATECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its water solubility and plasma stability are poor, and its activity is also low. It is expected to further improve its activity, water solubility and plasma stability by modifying its structure.

Method used

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  • Parthenolide dimer as well as salt, pharmaceutical composition and application thereof
  • Parthenolide dimer as well as salt, pharmaceutical composition and application thereof
  • Parthenolide dimer as well as salt, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the synthesis of compound 5-16

[0016] Synthesis of compound 1

[0017]

[0018] At 0°C, dissolve selenium dioxide (1.25g, 11.3mmol) in dichloromethane (60mL), add tert-butanol peroxide (4mL), and after 30 minutes, parthenolide (8.06g, 32.5 mmol) was dissolved in dichloromethane (65mL) and slowly added to the above system, and the reaction system was stirred at room temperature for 24 hours. After the plate reaction was completed, saturated sodium thiosulfate solution (125mL) was added, Extracted three times, the organic phase was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and passed through a silica gel chromatography column (petroleum ether / ethyl acetate=5:1 to 2:1) to obtain compound 1 (white solid, 5.38g, yield: 62.7 %) while obtaining compound 2 (white solid, 0.991 g, yield: 11.6%).

[0019] Synthesis of Compound 2

[0020]

[0021] Compound 1 (4.5 g, 17 mmol) dissolved in DCM solution (115 mL) was placed in...

Embodiment 2

[0040] Example 2: Pharmacological effects of parthenolide dimer or its salt

[0041] Match various cancer cells into 2×10 5 / mL cell suspension, add to 96-well round-bottom cell culture plate, add parthenolide dithiocarbamate derivative or its salt respectively, 3 wells for each test concentration, place at 37°C, 5% CO 2 Cultivate under saturated humidity conditions for 72 hours, use MTT method to measure the absorbance (A) value at the wavelength of 570nm of the enzyme-linked detector, calculate the inhibitory effect of the compound of the present invention on the test cancer cells, and repeat three times.

[0042] Table 1 The inhibitory activity (IC of parthenolide dimer) to various cancer cells 50 , μM)

[0043]

[0044] Among them, U87, U118, SF126, SHG44, U251, and C6 are brain tumor cell lines, and 3T3 is a normal fibroblast cell line.

[0045] The results of the activity test showed that the screened compounds exhibited inhibitory activity against the tested brain...

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PUM

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Abstract

The invention provides a parthenolide dimer as shown in a formula (I) and salt, a pharmaceutical composition and application thereof, and particularly relates to application of the parthenolide dimerand the salt thereof in preparation of drugs for treating cancers and auxiliary drugs for treating cancers.

Description

technical field [0001] The present invention relates to a pharmaceutical composition for treating cancer or adjuvantly treating cancer with parthenolide dimer and its salt as an active ingredient, and the application of the pharmaceutical compound and composition in the preparation of anticancer or auxiliary anticancer drugs. belongs to the field of pharmacy. Background technique [0002] Cancer stem cells, also known as tumor-initiating cells, refer to cancer cells with stem cell properties. Cancer stem cells can initiate tumors and drive tumor proliferation, can achieve unlimited proliferation of cancer cells through self-renewal, and can produce more mature ordinary cancer cells through differentiation [T.Reya,, S.J.Morrison,, M.F.Clarke, and I.L.Weissman,, Nature .2001, 414, 105–111.]. Since cancer stem cells play an important role in tumor initiation, metastasis and drug resistance [J.E.Visvader, G.J.Lindeman, Cell Stem Cell 2012,10,717-728], targeting cancer stem cel...

Claims

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Application Information

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IPC IPC(8): C07D519/00A61K31/365A61K31/77A61P35/00C08G65/332
CPCC07D519/00A61P35/00C08G65/3328
Inventor 陈悦张泉丁亚辉李静郭宏宇王蒙蒙
Owner ACCENDATECH