Preparation method of mango aglycone

Abstract

The invention discloses a method for preparing a natural active compound mangiferin. The method of the invention uses 2-halo-4,5-dimethoxybenzoyl chloride (the halogen can be a chlorine atom or a bromine atom) and 1,3 , 5-trimethoxybenzene is used as raw material, and high-purity mangiferin aglycone can be efficiently obtained through two-step reaction operations of Fuckers acylation reaction (condensation) and demethylation cyclization. The raw materials of this method are cheap and easy to obtain, and the synthesis steps Less, the operation is simpler, safer, more efficient, and easier to control. The synthesized products have high purity and excellent quality, and are suitable for industrial production applications.

Description

technical field [0001] The invention relates to a new chemical synthesis method of an important intermediate mangiferin aglycone which can be used for further preparing natural active compounds mangiferin compounds and related active derivatives, and belongs to the field of chemical synthesis. Background technique [0002] Mangiferin, also known as 1,3,6,7-tetrahydroxyxanone, or Norathyriol in English, is the aglycon of mangiferin, a pharmacologically active ingredient present in various plants such as mango leaves and almond leaves. Studies have found that mangiferin is the main active metabolite of mangiferin in vivo (Hui W, Guan Y, Chun-Hui M, Yi-Hong T, Ming-Song F, Zhi-Xiong L, Cheng-Gang Huang. J Pharm Biomed Anal . 2007; 45:793-798), has pharmacological activities such as anti-inflammatory, anti-oxidation, anti-tumor, hypoglycemic and anti-PTP1B. important intermediates. Mangiferin, mangiferin and many of its structural derivatives have been shown through pharmacolo...

AI Technical Summary

Problems solved by technology

Some literatures have reported the chemical synthesis of mangiferin aglycon (Bhatia, V.K.; Seshadri, T.R. Tetrahedron Letters (1968), (14), 1741-2), but the synthetic yield of this method is extremely low (7%, the raw material is not easy to obtain ), and the sources of raw materials for synthesis are very limited or difficult to obtain and have basically no application value

In 2010, Li Ling et al. from Kunming Medical College (Li Ling, Song Liudong et al. Application No. 201010529474.7) took 3,4-dihydroxybenzoic acid methyl ester as the starting material, through methylation, hydrolysis, bromination, Ullmann into etherification , cyclization, demethylation and other six-step reactions have obtained mangiferin. Although the raw materials are easy to obtain, highly toxic reagents such as dimethyl sulfate, bromine, boron tribromide and more expensive reagents such as Cesium carbonate, etc., the total reaction yield is only 5.12%, which cannot be well prepared in large quantities or meet the needs of production

[0004] In addition, in 2011, Lina Hu et al. reported another relatively good method for the synthesis of mangiferin aglycone. They used 2,4,5-trimethoxybenzoic acid as the starting material, through acyl chloride, Friedel-Crafts acylation, Mangiferin aglycones (Lina Hu , Honggang Hu et al. Discovery of novel xanthone derivatives as xanthine oxidase inhibitors. Bioorg. Med. Chem. Lett. 2011, 21, 4013–4015), the total yield is about 50%, but this method is still not as simple and efficient as the method of the present invention

Images