Substituted benzofuroylhydrazone derivatives and preparation method thereof

A technology of benzofuroylhydrazones and benzofuran, which is applied in the field of substituted benzofuroylhydrazone derivatives and their preparation, can solve problems that have not been reported, and achieve the effect of simple steps

Active Publication Date: 2019-07-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Therefore, the benzofuran carboxyhydrazone compounds and their derivatives with the furan ring substituted by methyl groups have potential pharmaceutical activity, and such compounds have not been reported so far.

Method used

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  • Substituted benzofuroylhydrazone derivatives and preparation method thereof
  • Substituted benzofuroylhydrazone derivatives and preparation method thereof
  • Substituted benzofuroylhydrazone derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045]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:

[0046]

[0047] Molecular formula: C 12 h 14 o 4

[0048] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate

[0049] English name: ethyl 3-me...

Embodiment 2

[0054] 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:

[0055]

[0056] Molecular formula: C 10 h 10 o 4

[0057] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid

...

Embodiment 3

[0064] 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:

[0065]

[0066] Molecular formula: C 9 h 10 o 2

[0067] Chinese name: 3-methy...

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PUM

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Abstract

The invention relates to the field of medical chemistry, and aims at providing a substituted benzofuran hydrazone derivative and a preparation method thereof. The product has a structure as shown in a formula (I), wherein B ring is selected from phenyl, furyl, thienyl and naphthyl; and R1, R2 and R3 are independently selected from hydrogen atoms, halogen, hydroxy, alkyl chain of C1-C7, alkoxy of C1-C7, nitryl or cyan. The benzofuran hydrazone derivative is a natural furan hydrazone derivative with a new frame, has potential medicinal activity; and the preparation of the compound can be used for supporting researches of benzofuran hydrazone medicinal activity. The preparation method is simple and easily available in steps, and has an important meaning for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, more specifically, to a substituted benzofuroylhydrazone derivative and a preparation method thereof. Background technique [0002] Acylhydrazone compounds are a class of Schiff base compounds formed by the condensation of hydrazides and aldehydes or ketones, which exhibit good biological activity, strong coordination ability and diverse coordination modes in a biophilic environment. It has received extensive attention in the fields of medicine, pesticides, materials and analytical reagents. There have been a large number of literature reports and wide applications in luminescent materials, fluorescence analysis, metalloenzyme simulation, and clinical treatment of certain diseases. [0003] Acylhydrazone compounds contain nitrogen atoms and oxygen atoms at the same time, so they can participate in the formation of hydrogen bonds in organisms, increase the affinity between receptors, and may in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/79C07D409/12A61K31/343A61K31/381
CPCC07D307/79C07D409/12
Inventor 何兴瑞吴军商志才顾海宁
Owner ZHEJIANG UNIV
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