Natural product 5,7-dimethoxy-4'-hydroxyisoflavone preparation method

A technology of hydroxyisoflavone and dimethoxy, which is applied in the direction of organic chemistry and can solve the problem of low yield

Inactive Publication Date: 2009-12-30
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above two chemical synthesis methods not only have low yields, but also need to use expensive reagents such as thallium nitrate

Method used

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  • Natural product 5,7-dimethoxy-4'-hydroxyisoflavone preparation method

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Embodiment 1

[0025] (1) Synthesis of 2-(4-benzyloxyphenyl)acetic acid (2)

[0026] A water / ethanol (10 / 80mL) solution of potassium hydroxide (4.94g, 88mmol) was added to a suspension composed of p-hydroxyphenylacetic acid (6.08g, 40mmol) and ethanol (20mL), and the reaction mixture was heated at room temperature Stir at low temperature for 5 min, then add benzyl bromide (9.5 mL, 13.68 g, 80 mmol). The reaction mixture was heated to reflux for 2.5 h and cooled to room temperature. Ethanol was distilled off, and 100 mL of 10% sodium hydroxide solution was added to the residue, followed by extraction with ether (30 mL×2). The aqueous phase was acidified with concentrated hydrochloric acid, then extracted with ethyl acetate (30 mL×2), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain 7.0 g of white crystals of product 2, yield 72%; m.p. 123°C.

[0027] (2) Synthesis of 2-(4-benzyloxyphenyl)acetyl chlo...

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Abstract

The invention relates a natural product 5,7-dimethoxy-4'-hydroxyisoflavone preparation method, comprising the following steps: adopting 4-hydroxylphenylacetic acid and 3,5-dimethoxyphenol as starting materials to perform Fries rearrangement reaction to generate hydroxydeoxybenzoin compound 1-(2,4-dimethoxy-6-hydroxylphenyl)-2-(4-hydroxylphenyl)ethanone; adopting N,N-dimethylformamide (DMF) as formylation reagent and solvent and adding methanesulfonyl chloride at the same time to promote Vilsmeier-Haack formylation reaction and consecutive cyclization reaction and increase the yield of 5,7-dimethoxy-4'-hydroxyisoflavone (1). The invention is simple and practical, the raw materials are cheap and accessible and the yield is high so that the preparation method is applicable to industrialized production.

Description

technical field [0001] The invention belongs to the field of isoflavone preparation, in particular to a preparation method of natural product 5,7-dimethoxy-4'-hydroxy isoflavone. Background technique [0002] Diabetes and obesity are endocrine disorders and metabolic diseases that seriously threaten people's health, often accompanied by decreased sensitivity to insulin in peripheral tissues and disordered regulation of insulin signaling pathways. An important regulatory mechanism in the insulin signaling pathway is the reversible regulation of protein tyrosine phosphorylation of insulin receptor (insulin receptor, IR), insulin receptor substrate (insulin receptor substrate, IRS) and other downstream molecules. In 2006, Na et al. reported that 5,7-dimethoxy-4′-hydroxyisoflavone (1) and its analogs were isolated from the root of the leguminous plant Erythrina mildbraedii, and these flavonoids exhibited inhibitory activity against PTP1B , may become a new class of PTP1B inhibi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36
Inventor 李洪启陈东玲金叶李金星
Owner DONGHUA UNIV
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