Method for preparing 1,3,6,7-tetrahydroxy xanthone

A technology of hydroxydiphenpyrone and demethylation, which is applied in the direction of organic chemistry and the like, can solve the problems that the preparation of mangiferin aglycone cannot be widely used, the yield of mangiferin aglycone is low, the synthesis route is long, etc., and the raw materials are cheap and raw materials are achieved. The effect of easy availability and short synthetic route

Active Publication Date: 2012-12-26
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] At present, the method of synthesizing mangiferin aglycone (Masao Fujita, Takao Inoue, Chem.Pharm.Bull, 28 (8), 2482-2486, 1980) recorded in the article published by Masao Fujita etc. is mostly used in the chemical synthesis of mangiferin aglycone, but This synthetic method has a long synthetic route, poor selectivity, and the yield of mangiferin aglycone is extremely low, only about 7%, so it cannot be widely used in the preparation of mangiferin aglycone

Method used

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  • Method for preparing 1,3,6,7-tetrahydroxy xanthone
  • Method for preparing 1,3,6,7-tetrahydroxy xanthone

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Embodiment 1

[0027] Embodiment 1: the method of the present invention prepares 1,3,6,7-tetrahydroxybivafen

[0028] Weigh 2.166g (10mmol) 2-chloro-4,5-dimethoxybenzoic acid and 2.018g (12mmol) 1,3,5-trimethoxybenzene into a 50mL single-necked round-bottomed flask, then add successively Zinc chloride hydrate 1.363g (10mmol) and phosphorus oxychloride 28.9ml (310mmol), turn on the magnetic stirring, heat the reaction at 75°C for about 3h, then let the reaction solution cool down. Add 30mL of water and 20mL of dichloromethane to the reaction solution, stir well and let it stand, separate the water layer after separating the organic layer and extract it with 20mL of dichloromethane for 4 times, combine the organic layers, dry over anhydrous sodium sulfate and evaporate to dryness under reduced pressure The crude product of 1,3,6,7-tetramethoxybispyrazone was obtained by solvent, and the silica gel column chromatography (petroleum ether / ethyl acetate=4:1) gave 1,3,6,7-tetramethoxybis Pure phen...

Embodiment 2

[0031] Embodiment 2: the method of the present invention prepares 1,3,6,7-tetrahydroxybivafen

[0032] Weigh 2.026g (10mmol) of 2-chloro-4-methoxy-5-hydroxybenzoic acid and 2.018g (12mmol) of 1,3,5-trimethoxybenzene into a 50mL single-necked round bottom flask, and then add Anhydrous zinc chloride 1.363g (10mmol) and phosphorus oxychloride 28.9ml (310mmol), magnetic stirring was turned on, and after heating at 75°C for about 3 hours, the reaction solution was left to cool. Add 30mL of water and 20mL of dichloromethane to the reaction solution, stir well and let it stand, separate the water layer after separating the organic layer and extract it with 20mL of dichloromethane for 4 times, combine the organic layers, dry over anhydrous sodium sulfate and evaporate to dryness under reduced pressure Solvent to obtain 6-hydroxyl-1,3,7-trimethoxybispyrazone crude product, silica gel column chromatography (petroleum ether / ethyl acetate=4:1) to obtain 6-hydroxyl-1,3,7-trimethoxy 0.871g...

Embodiment 3

[0035] Embodiment 3: The method of the present invention prepares 1,3,6,7-tetrahydroxybivafen

[0036] Weigh 4.332g (20mmol) 2-chloro-4,5-dimethoxybenzoic acid and 4.036g (24mmol) 1,3,5-trimethoxybenzene into a 150mL single-necked round-bottomed flask, and then add successively 3.467g (26mmol) of aluminum chloride hydrate and 63.6mL (682mmol) of phosphorus oxychloride were turned on magnetic stirring, and after heating at 80°C for about 4 hours, the reaction solution was left to cool. Add 70mL of water and 50mL of chloroform to the reaction solution, stir well and let it stand, separate the water layer after separating the organic layer and extract with 50mL of chloroform for 4 times, combine the organic layers, dry over anhydrous sodium sulfate and evaporate the solvent to dryness under reduced pressure to obtain 1,3 , The crude product of 6,7-tetramethoxybislipram was recrystallized to obtain 1.613 g of pure 1,3,6,7-tetramethoxybislipram, with a yield of 31%, as white crysta...

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Abstract

The invention, relating to the field of pharmaceutical chemistry, particularly relates to a method for preparing 1,3,6,7-tetrahydroxy xanthone. According to the invention, 1,3,6,7-tetrahydroxy xanthone can be synthesized through two steps, the synthesis route is short, the steps are few, the operation is simple and easy to control, the prepared 1,3,6,7-tetrahydroxy xanthone has high purity and can be widely applied in industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for preparing 1,3,6,7-tetrahydroxybivafen. Background technique [0002] 1, 3, 6, 7-Tetrahydroxybiphenylpyrrole, also known as mangiferin, and its English name is Norathyriol, is present in the leaves, fruits and bark of Liliaceae Anemarrhena, Anacardiaceae mango trees, almond trees, The aglycon of mangiferin, a biologically active component of the Phytaceae plant Guangshiwei, etc., has a chemical structural formula as shown in Formula I: [0003] [0004] Modern pharmacological studies have shown that mangiferin, as a potent inhibitor of protein tyrosine phosphatase 1B (PTP1B), has a significant effect of lowering animal blood sugar, lowering uric acid, anti-gout and anti-tumor activity. It has a potential wide application in the treatment of diseases related to abnormal function of tyrosine phosphatase 1B, such as diabetes, gout, obesity and other metabolic syndr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86
Inventor 李鹏辉高小惠张伟
Owner KPC PHARM INC
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