Preparation method of mango aglycone

Abstract

The invention discloses a preparation method of a natural active compound of mango aglycone. The preparation method comprises the following steps: getting 2-halogenate-4, 5-dimethoxy benzoyl chloride (halogen can be helium atom or bromine atom) and 1, 3, 5-trimethoxy benzene as the raw materials; and carrying out Friedel-Crafts acylation reaction (condensation) and demethylation cyclization to same to efficiently obtain the high-purity mango aglycone. According to the preparation method disclosed by the invention, the raw materials are cheap and easy to obtain; fewer synthesizing steps are carried out, therefore, the operation can be simpler, more convenient, safer and more efficient; and the preparation method is easy to control; the synthesized product is high in purity, and has high quality; and the preparation method is suitable to be applied to industrial production.

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...

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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

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