Benzofuran fluoroflavanone derivative and preparation method thereof

A technology for benzofuran fluoroflavanone and furan fluoroflavanone, which is applied in the field of benzofuran fluoroflavanone derivatives and their preparation, and achieves the effects of low loss rate and simple steps

Active Publication Date: 2017-06-30
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, benzofuran fluoroflavanones and their derivatives have

Method used

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  • Benzofuran fluoroflavanone derivative and preparation method thereof
  • Benzofuran fluoroflavanone derivative and preparation method thereof
  • Benzofuran fluoroflavanone derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0042]Disperse 1,3-cyclohexanedione and potassium hydroxide uniformly in water, stir at room temperature for 5 minutes, add methanol solution of ethyl chloroacetoacetate, then stir the system at room temperature for 5 days, and then use 4N Acidify with hydrochloric acid, filter the acidified reaction solution, and the obtained solid is the product: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate. In this step, the molar ratio of 1,3-cyclohexanedione to potassium hydroxide and ethyl chloroacetoacetate is 1:1:1, and the feeding amount of 1,3-cyclohexanedione corresponding to every milliliter of water is 0.1g , the feeding amount of ethyl chloroacetoacetate corresponding to every milliliter of methanol is 0.2g. The yield for this step was 65%. The structure of the resulting product is:

[0043]

[0044] Molecular formula: C 12 h 14 o 4

[0045] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate

[0046] English name: ethyl 3-me...

Embodiment 2

[0051] Dissolve ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate and potassium hydroxide in a mixed solvent of methanol and water, and stir the system at room temperature after dissolution Reaction 5h. Then adjust the pH of the reaction solution to 1 with 6N hydrochloric acid, filter the reaction solution, and filter the obtained solid as the product: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2- formic acid. The mixed solvent used in this step is methanol and water at a ratio of 2.5:1. The feeding amount of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate per milliliter of mixed solvent is 0.2 g. In this step, the molar ratio of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate to potassium hydroxide was 1:6. The yield for this step was 90%. The structure of the resulting product is:

[0052]

[0053] Molecular formula: C 10 h 10 o 4

[0054] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid

...

Embodiment 3

[0060] Disperse 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid evenly in diethylene glycol, add copper powder and pyridine, then heat the system to 175°C, Keep stirring for 10h. Cool the system to room temperature, add ice water, and acidify with 4N hydrochloric acid, extract the acidified reaction solution with petroleum ether three times, wash the combined extract with water once, then dry the extract with anhydrous sodium sulfate, and spin dry. The obtained solid is the product: 3-methyl-6,7-dihydrobenzofuran-4-(5H)-one. In this step, the feeding amount of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid per milliliter of diethylene glycol is 0.1 g. In this step, the molar ratio of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid to copper powder and pyridine is 1:1:2. The yield for this step was 85%. The structure of the resulting product is:

[0061]

[0062] Molecular formula: C 9 h 10 o 2

[0063] Chinese name: 3-methy...

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Abstract

The present invention relates to the field of pharmaceutical chemistry. A purpose of the present invention is to provide a benzofuran fluoroflavanone derivative and a preparation method thereof, wherein the product has a structure represented by a formula (I), the ring B is selected from phenyl or furyl, and R1, R2 and R3 are independently and respectively selected from hydrogen atom, halogen, cyano, nitro, a C1-C7 alkyl chain and C1-C7 alkoxy. According to the present invention, the benzofuran fluoroflavanone derivative is a class of the benzofuran flavone analogs having the new skeleton, and has potential pharmacological activity; the preparation of the compound can provide the support for the research of the pharmacological activity of the benzofuran flavone; and the preparation method has advantages of simple step and low loss rate, is the completely-new benzofuran flavone derivative synthesis route from the non-aromatic raw material, and provides important significance for the industrial production. The formula (I) is defined in the specification.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, more specifically, to a benzofuran fluoroflavanone derivative and a preparation method thereof. Background technique [0002] Flavonoids, widely distributed in natural plants, have attracted extensive attention due to their various biological activities. Studies have found that flavonoids and their derivatives have anticancer, anti-inflammatory, antioxidative, antiparasitic, antibacterial and other activities. [0003] Methyl-substituted furan ring structures widely exist in natural products and have diverse biological activities. For example, tanshinone can treat cardiovascular diseases, furofroxane has phytoallelopathy, and sesquiterpenoid cacalol has anti-hyperglycemic and antibacterial effects. [0004] At present, considerable progress and achievements have been made in the research of fluorine-containing drugs. Such as central nervous system drugs, antineoplastic drugs, antimicrobial d...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/352A61P35/00A61P29/00A61P39/06A61P9/00
CPCC07D493/04
Inventor 何兴瑞吴军商志才顾海宁
Owner ZHEJIANG UNIV
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