Method for preparing mangiferin aglycone

A technology of mangiferin and compounds, which is applied in the field of medicinal chemistry, can solve the problems that mangiferin cannot be widely used in chemical synthesis, the content of mangiferin and mangiferin is small, and the amount of mangiferin preparation cannot meet the requirements, and the price of raw materials can be achieved. Inexpensive, less synthetic steps, easy to control the effect

Active Publication Date: 2012-07-18
KPC PHARM INC +1
View PDF4 Cites 21 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, mangiferin is basically extracted and purified from mango leaves and almond leaves. For example, Chinese patent CN200810196777.4 discloses mangiferin and its preparation and purification methods and applications, but mangiferin in mango leaves and almond leaves The content of mangiferin and mangiferin is very small, and the amount of mangiferin prepared by this extraction and purification method is far from meeting the current and future needs. Therefore, it is of great significance to prepare a large amount of mangiferin by chemical synthesis.
There is a literature report on a chemical synthesis method for the synthesis of mangiferin aglycone, but the synthesis yield of this method is extremely low, only about 7%, and the source of synthetic raw materials is very limited, so that the chemical synthesis method cannot be widely used in the preparation of mangiferin aglycone middle

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing mangiferin aglycone
  • Method for preparing mangiferin aglycone
  • Method for preparing mangiferin aglycone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: Mangiferin aglycon is prepared by the method of the present invention

[0044] Weigh 5.04g (0.02mol) of 2-chloro-4,5-dimethoxybenzoic acid and 3.40g (0.02mol) of 1,3,5-trimethoxybenzene into a 100ml three-necked reaction flask, stir 2ml of anhydrous hydrogen fluoride and 20ml of solvent chloroform were added. The mixture was heated to 80°C, stirred and reacted for 10 h, then allowed to cool, added 50 ml of water and 30 ml of chloroform, stirred well and left to stand, separated the organic layer, extracted the water layer once with 50 ml of chloroform, combined the organic layers obtained twice, Washed once with water and semi-saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to remove the solvent under reduced pressure to obtain a solid, and then recrystallized to obtain 5.7 g of a compound with the structure of formula IV, with a yield of 70%. In formula IV, X is Cl, represented...

Embodiment 2

[0049] Embodiment 2: the method of the present invention prepares mangiferin aglycon

[0050] Weigh 5.22g (0.02mol) of 2-bromo-4,5-dimethoxybenzoic acid and 3.40g (0.02mol) of 1,3,5-trimethoxybenzene into a 100ml three-necked reaction flask, stir 5.0 g of phosphorus pentoxide and 20 ml of solvent trichlorethylene were added. Heat the mixture to 120°C, stir and react for 10 hours, then let it cool, add 50ml of water and 30ml of dichloromethane, stir well and let stand, separate the organic layer, extract the water layer with 50ml of dichloromethane once more, and combine the obtained two times The organic layer was washed once with water and semi-saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure to obtain a solid, and then recrystallized to obtain 5.8 g of a compound with the structure of formula IV. The yield was 71%, where X is Br in the formula IV, represented by IV-Br, its nu...

Embodiment 3

[0055] Embodiment 3: Mangiferin aglycon is prepared by the method of the present invention

[0056] Weigh 5.40g (0.02mol) of 2-iodo-4,5-dimethoxybenzoic acid and 3.40g (0.02mol) of 1,3,5-trimethoxybenzene into a 100ml three-necked reaction flask, stir 2.0 ml of phosphorus oxychloride and 20 ml of solvent 1,2-dichloroethane were added. Heat the mixture to 120°C, stir and react for 10 hours, let it cool, add 50ml of water and 30ml of 1,2-dichloroethane, stir well and let it stand, separate the organic layer, and wash the water layer with 50ml of 1,2-dichloroethane Extract with alkane again, combine the organic layers, wash with water and semi-saturated aqueous sodium bicarbonate solution once, dry over anhydrous sodium sulfate, filter, and evaporate the filtrate to obtain a solid under reduced pressure to remove the solvent, and then recrystallize to obtain compound 5.9 with the structure of formula IV g, the yield is 72%, wherein X is I in formula IV, expressed with IV-I, and ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to the field of medicinal chemistry, and discloses a method for preparing mangiferin aglycone. The method comprises that: step 1, 2-halogenate-4,5-dimethoxy benzoic acid and 1,3,5-trimethoxy benzene are subjected to Friedel-Crafts reaction, so a compound which has a structure in a formula IV is generated; step 2, the compound in the formula IV is selectively demethylated, and a compound which has the structure in the formula V is generated; step 3, the compound in the formula V is cyclized, and a compound which has the structure in the formula VI is generated; and step 4, the compound in the formula VI is completely demethylated, and mangiferin aglycone is generated. The method for preparing mangiferin aglycone improves the synthetic yield of the mangiferin aglycone, has the characteristics of cheap and easily-obtained raw materials, less synthetic steps, convenience in operation, easiness in control and high product 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 mangiferin. Background technique [0002] Mangiferin, the scientific name is 1,3,6,7-tetrahydroxybifenapyrone, and the English name is Norathyriol, which is the aglycone of the pharmacologically active ingredient mangiferin present in mango leaves and almond leaves, and its chemical structure is as follows: I show: [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 syndromes, as well as tumors. In addition, mangiferin is also an important intermediate for the synthesis of natural...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86
Inventor 杨健杨兆祥杨波张伟周荣光李鹏辉
Owner KPC PHARM INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap