Preparation method and usage for nitrogen-containing flavone derivatives

A technology of derivatives and flavonoids, applied in the field of organic compound synthesis, can solve problems such as inefficiency, and achieve the effects of low production cost, mild reaction conditions and easy operation

Inactive Publication Date: 2007-09-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But FAA Shows Inefficiency in Clinical Trials

Method used

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  • Preparation method and usage for nitrogen-containing flavone derivatives
  • Preparation method and usage for nitrogen-containing flavone derivatives
  • Preparation method and usage for nitrogen-containing flavone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: 2-hydroxy-4,6-dimethoxy-3-allyl acetophenone (compound III)

[0024] 3.9g (20.0mmol) of compound I, 4g (30.0mmol) of anhydrous potassium carbonate and 30mL of anhydrous acetone were put into the reaction flask, and 17.3mL (20.0mmol) of allyl bromide was added dropwise with stirring. After the addition, the temperature was raised to reflux for 4 hours. The reaction solution was cooled and filtered with suction, and the filtrate was evaporated to remove the solvent to obtain 4.5 g of compound II, which was directly used in the next reaction.

[0025] Compound II was dissolved in DMF (20mL), heated and refluxed for 6h, the reaction solution was distilled off the solvent under reduced pressure, diluted with water, extracted with dichloromethane (40mL×3), washed with saturated sodium chloride solution (40mL×3), anhydrous Na2SO4 dried. After filtration, the filtrate was recovered under reduced pressure, and the crude product was subjected to column chromatography...

Embodiment 2

[0026] Embodiment 2: 2-chlorobenzoic acid-(2-acetyl-3,5-dimethoxy-6-allyl)phenol ester (compound IV 1 )

[0027] 2.4 g (10.0 mmol) of compound III was dissolved in 16 mL of dry pyridine, and 1.9 g (11.0 mmol) of o-chlorobenzoyl chloride was slowly added dropwise under cooling in an ice-water bath. After the addition was complete, stir overnight at room temperature. The dilute HCl solution containing crushed ice was poured into the above reaction solution and stirred evenly, a white solid was precipitated, filtered with suction, and the solid was dried under reduced pressure, with a yield of 86%.

Embodiment 3

[0028] Embodiment 3: 4-trifluoromethylbenzoic acid-(2-acetyl-3,5-dimethoxy-6-allyl)phenol ester (compound IV 2 )

[0029] Compound III 1.5g (6.4mmol) and p-trifluoromethylbenzoic acid 1.4g (6.9mmol) were dissolved in dry pyridine 16mL, and SOCl was slowly added dropwise at room temperature 2 (0.4 mL). After addition, stir at room temperature for 12h. The dilute HCl solution containing crushed ice was poured into the above reaction solution and stirred evenly, a white solid was precipitated, filtered with suction, and the solid was dried under reduced pressure, with a yield of 86%.

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Abstract

The invention discloses a 8-alkylamine propyl-5, 7-disubstituted flavone derivant, which is characterized by the following: adopting flavone with tumour-proof activity as primer; introducing different alkylamine propyls into 8-position of mother core of flavone; synthesizing a series of product with ECA-109, A-549, HL-60, PC-3 and so on to inhibit external breeding.

Description

technical field [0001] The present invention belongs to the synthesis of organic compounds, and relates to a preparation method of nitrogen-containing flavone derivatives, in particular to a preparation method of 8-alkylaminopropyl-5,7-disubstituted flavone derivatives, and its application in the preparation of antitumor drugs . Background technique [0002] Flavonoid derivatives have antitumor effects. As early as 1971, the US National Cancer Institute (NCI) used the P388 leukemia model to screen more than 200 flavonoids for anti-tumor activity, and found that quercetin (3′,4′,5,7-tetrahydroxyflavone) has Certain activity. Since then, people have successively reported a variety of flavonoids with antitumor activity and their mechanism of action. Flavone-8-acetic acid (FAA) was once a flavone derivative that received much attention. NCI research shows that FAA is active against almost all solid tumors inoculated in mice, such as colon cancer, pancreatic duct adenocarcino...

Claims

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Application Information

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IPC IPC(8): C07D311/28A61K31/352A61K31/5375A61K31/496A61K31/4025A61P35/00
Inventor 刘滔徐仲淼胡永洲何俏军杨波杨晓春
Owner ZHEJIANG UNIV
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