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Preparation method and application of dibenzofuran compound

A technology of diphenylfuran and compounds, applied in the field of preparation and application of diphenylfuran compounds, can solve the problems of low content of natural active compounds, limited resource sources, complex extraction and separation, etc., to achieve inhibition of proliferation, easy availability of raw materials, and high rate effect

Active Publication Date: 2017-10-24
KUNMING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The content of natural active compounds in animal and plant resources is often very low, and the source of resources is limited. The extraction and separation are complicated and costly, which is the biggest obstacle to the development and application of natural active compounds.

Method used

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  • Preparation method and application of dibenzofuran compound
  • Preparation method and application of dibenzofuran compound
  • Preparation method and application of dibenzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Diphenylfuran compounds of the present invention: 6-acetyl-2-(1-amino-ethylene)-7,9-dihydroxy-8,9b-dimethyl-9bH-diphenylfuran-1,3- The chemical synthesis and structure identification of diketone (6-Acetyl-2-(1-amino-ethylene)-7,9-dihydroxy-8,9b-dimethyl-9bH-dibenzofuran-1,3-dione).

[0058] Using D-lichenic acid (CAS: 7562-61-0, (+)-Usnic Acid) and hexamethyldisilazane (CAS: 999-97-3, C 6 h 19 NSi 2 or (Me 3 Si) 2 NH) is chemically synthesized as substrates in different solvent media. The results show that using chloroform or ethyl acetate as the solvent medium is the best, the product yield is high, easy to purify, high in purity, and the process is simple. The product yield in methanol and ethanol medium is low, and many impurity by-products will be formed in acetone medium, and the synthesis reaction cannot be carried out in petroleum ether and oily medium. The mol ratio of D-lichenic acid and hexamethyldisilazane is preferably 1:1.7-2.1; the preferred ratio of...

Embodiment 2

[0072] Example 2: Compound 6-acetyl-2-(1-amino-ethylene)-7,9-dihydroxy-8,9b-dimethyl-9bH-diphenylfuran-1 represented by formula (I) , the antitumor effect of 3-diketone (6-Acetyl-2-(1-amino-ethylene)-7,9-dihydroxy-8,9b-dimethyl-9bH-dibenzofuran-1,3-dione), combined antitumor Biological experiment results of action, toxicological safety and anti-tumor mechanism

[0073] The formula (I) compound 6-acetyl-2-(1-amino-ethylene)-7,9-dihydroxyl-8,9b-dimethyl-9bH- Diphenylfuran-1,3-dione has significant, selective, cell-targeted anti-tumor effects, and combined anti-tumor effects with clinical anti-tumor drugs, anti-tumor effects are superior to clinical anti-tumor drugs, and its toxicology Safety and antitumor mechanism of action.

[0074] 1. The effect of diphenylfuran compounds of the present invention on inhibiting and killing human cancer cells in vitro:

[0075] In vitro anti-tumor test method: the diphenylfuran compound of the present invention is dissolved in analytically p...

Embodiment 3

[0107] Example 3: Compound 6-acetyl-2-(1-amino-ethylene)-7,9-dihydroxy-8,9b-dimethyl-9bH-diphenylfuran-1 represented by formula (I) , The mechanism of anticancer action of 3-diketone

[0108] 1. Effect on the growth cycle of cancer cells

[0109] The cell culture test method is the same as the aforementioned in vitro anticancer test method. After the liver cancer cell HepG2 was treated with the diphenylfuran compound represented by formula (I) (at a dose of 1.0 μg / ml) for 48 hours, the cell cycle and apoptosis were detected by flow cytometry (FACS). The positive control group was cisplatin (DDP, 1.5 μg / ml) and 5-fluorouracil (5-Fu, 5.0 μg / ml). The results are shown in Table 4.

[0110] Results: The diphenylfuran compounds represented by the formula (I) can significantly affect the differentiation and cycle of cancer cells, block the cells in the G2 / M phase, and reduce the cells in the G0 / G1 phase and S phase.

[0111] Table 4. Effects on cell cycle (HepG2 cells)

[0112] ...

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Abstract

The invention relates to a preparation method and application of a dibenzofuran compound and belongs to the technical field of medicinal chemistry. The structure of the compound is shown as formula (I). The preparation method comprises the following steps: taking d-usninic acid and hexamethyl disilazane as substrates and then performing amination synthetic reaction in an organic solvent medium under room temperature. The preparation method is characterized by easily acquired raw materials, simple and quick compounding steps, easiness in purifying and high yield of products and low cost. After the compound is fed into the stomach through the mouth of the rat, no acute toxicity exists, the compound has no obvious toxic influence on animal weight increasing, viscera development, blood biochemistry and blood routine index under the valid anticancer dosage and the compound can obviously increase the total serum protein and albumin level. The compound provided by the invention has an antitumor function and a joint antitumor function with clinic antitumor drugs, can be used for preparing antitumor chemical treatment drugs, antitumor drug compounds and auxiliary antitumor healthcare products and has wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a preparation method and application of a diphenylfuran compound, which is 6-acetyl-2-(1-amino-ethylene)-7,9-dihydroxy-8 ,9b-Dimethyl-9bH-diphenylfuran-1,3-dione (English structural name: 6-Acetyl-2-(1-amino-ethylidene)-7,9-dihydroxy-8,9b-dimethyl- 9bH-dibenzofuran-1,3-dione). Background technique [0002] Malignant tumor is a major disease that seriously threatens human health and life safety. It has become the main cause of death of human beings and seriously threatens human health and life safety. According to data released by the International Cancer Institute of the World Health Organization in Globocan, there were 12.661 million new cancer cases and 7.564 million deaths worldwide in 2008; among them, 2.816 million new cancer cases and 1.958 million deaths in China. In 2012, there were 14.1 million new cancer cases in the world, 8.2 million deaths, and 32.6 milli...

Claims

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Application Information

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IPC IPC(8): C07D307/91A61K31/343A61K31/337A61K31/513A61K33/24A61K31/675A61P35/00A23L33/10
CPCA23V2002/00A61K31/337A61K31/343A61K31/513A61K31/675A61K33/24A23L33/10C07D307/91A61K2300/00A23V2200/308
Inventor 贺小琼
Owner KUNMING MEDICAL UNIVERSITY
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