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Substituted furanchalcone derivatives and preparation method thereof

A technology for furochalcone and derivatives, applied in the field of medicine, can solve problems such as unreported, and achieve the effects of simple steps and low loss rate

Active Publication Date: 2019-02-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the furanchalcones and their derivatives with the furan ring substituted by methyl have potential pharmaceutical activity, and such compounds have not been reported so far

Method used

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  • Substituted furanchalcone derivatives and preparation method thereof
  • Substituted furanchalcone derivatives and preparation method thereof
  • Substituted furanchalcone derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 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:

[0038]

[0039] Molecular formula: C 12 h 14 o 4

[0040] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate

[0041] English name: ethyl 3-m...

Embodiment 2

[0046] 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:

[0047]

[0048] Molecular formula: C 10 h 10 o 4

[0049] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid

...

Embodiment 3

[0055] 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:

[0056]

[0057] Molecular formula: C 9 h 10 o 2

[0058] Chinese name: 3-methy...

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Abstract

The invention relates to the field of medical chemistry, and aims at providing a substituted furan chalcone derivative and a preparation method thereof. The substituted furan chalcone derivative has the structure shown in a formula (I): wherein B ring is selected from phenyl, furyl or thienyl; R1, R2, and R3 are respectively and independently selected from hydrogen atom, halogen, hydroxyl, cyan, nitro, C1-C7 alkyl chain, C1-C7 alkoxy, and dimethylamino or diethylamino. The product is a kind of natural furan chalcone analogues with a new framework, the product has potential medicament activity, and the preparation of the compound can provide support for activity researches of furan chalcone medicaments. The preparation method has simple steps and low loss late, and provides a brand new route for synthesis of the furan chalcone derivative from nonaromatic raw materials. The method has an important meaning for industrial production.

Description

technical field [0001] The invention relates to the field of medicine, more specifically, to a substituted furacalcone derivative and a preparation method thereof. Background technique [0002] Chalcones belong to flavonoids and are widely distributed in natural plants. The chemical structure of chalcones is 1,3-diphenyl-2-propen-1-one. They have attracted extensive attention due to their various biological activities. Studies have found that chalcones 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, such as tanshinone can treat cardiovascular diseases, furofromane has phytoallelopathy, sesquiterpenoid cacalol has anti-hyperglycemic and Antibacterial effect. [0004] Therefore, furanchalcone compounds and their derivatives with furan rings substituted by methyl groups have poten...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/79C07D407/06C07D409/06
CPCC07D307/79C07D407/06C07D409/06
Inventor 吴军何兴瑞娄永根商志才顾海宁
Owner ZHEJIANG UNIV