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Mangiferin aglycon derivative, as well as preparation method and application of the mangiferin aglycon derivative

A mangiferin aglycone and derivative technology, applied in the field of compounds, can solve the problems of poor solubility and limitation, and achieve the effects of good development and utilization value, good reproducibility and high yield

Active Publication Date: 2011-08-17
SHANGHAI CHANGZHENG HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the clinical application of mangiferin is greatly limited due to poor solubility and other reasons.

Method used

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  • Mangiferin aglycon derivative, as well as preparation method and application of the mangiferin aglycon derivative
  • Mangiferin aglycon derivative, as well as preparation method and application of the mangiferin aglycon derivative
  • Mangiferin aglycon derivative, as well as preparation method and application of the mangiferin aglycon derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Preparation of 1,3,6,7-tetrahydroxy-xanthone (VI)

[0051] Please refer to the attached figure 1 , with figure 1 Is the preparation flow chart of 1,3,6,7-tetrahydroxy-xanthone.

[0052] (1) Preparation of 2,4,5-trimethoxybenzoyl chloride (II)

[0053] 25.00g (118mmol) of 2,4,5-trimethoxybenzoic acid was heated to reflux for 4 hours in the presence of 80mL of thionyl chloride to generate 26.80g of 2,4,5-trimethoxybenzoyl chloride (II), the yield 99%.

[0054] (2) Preparation of (2-hydroxy-4,5-dimethoxyphenyl)-(2,4,6-trimethoxyphenyl)-methanone (IV)

[0055] 26.80g (116.00mmol) of 2,4,5-trimethoxybenzoyl chloride and 20.00g (120.00mmol) of 1,3,5-trimethoxybenzene in 30.00g (220.00mmol) of anhydrous aluminum trichloride 30.40 g of (2-hydroxy-4,5-dimethoxyphenyl)-(2,4,6-trimethoxyphenyl)-methanone (IV) was produced at room temperature for 48 hours, with a yield of 75 %.

[0056] (3) Preparation of 1,3,6,7-tetramethoxy-xanthone (V)

[0057] (2-Hydroxy-4,5-dim...

Embodiment 2

[0060] Example 2 Preparation of target compound (X-1)

[0061] Please refer to the attached figure 2 , with figure 2 is a flow chart for the preparation of the target compound (X-1).

[0062] (1) Preparation of 1-hydroxy-3,6,7-tris(methoxymethoxy)-xanthone (VII)

[0063] 1,3,6,7-Tetrahydroxy-xanthone (VI) 2.60g (10.00mmol) in 4.1mL N,N - In the presence of diisopropyl, react with 2.50mL (31.00mmol) of chloromethyl methyl ether in an ice bath for 1h, the solvent is 150mL of dichloromethane, and then at room temperature for 8h, to obtain 1-hydroxyl-3,6,7-tri( Methoxymethoxy)-xanthone (VII) 2.20g, the pure product was obtained by column chromatography, and the yield was 55%.

[0064] (2) Preparation of compound (VIII)

[0065] 1-Hydroxy-3,6,7-tris(methoxymethoxy)-xanthone (VII) 2.20g (5.50mmol), add 8mL pyridine and 0.75g (8.30mmol) propane to 15mL acetone solution Acyl chloride was reacted under ice bath for 1.5 h to obtain 2.23 g of white solid (VIII), with a yield of ...

Embodiment 3

[0068] Example 3 Preparation of target compound (X-2)

[0069] At 0°C, dissolve VI 2.00g (5.40mmol) in 8mL pyridine and 10mL acetone solution, slowly add 1.25g (13.50mmol) propionyl chloride, and stir for 1.5h to obtain the target compound X-2 2.00g, please refer to attached image 3 , with image 3 Is the preparation flow diagram of the target compound (X-2), the yield is 70%. 1 H NMR (600MHz, DMSO) δ: 12.599 (1H, s, OH), 11.143 (1H, s, OH), 7.767 (1H, s, Ar-H), 6.971 (1H, s, Ar-H), 6.379 -6.382 (1H, d, J =1.8HZ, Ar-H), 6.211-6.214 (1H, d, J =1.8HZ, Ar-H), 2.571-2.643 (4H, m, 2CH 2 ), 1.139-1.263 (6H, m, 2CH 3 ); 13 C NMR(150MHz, DMSO) δ: 188.5, 169.1, 168.9, 162.5, 160.8, 160.3, 151.5, 143.2, 142.4, 123.5, 116.3, 111.7, 105.8, 96.3, 55.5, 60.0 MS, 9 (IES ) m / z calcd. for C 19 h 16 o 8 372.1, found [M-H] + 371.1.

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Abstract

The invention relates to a mangiferin aglycon derivative which has the chemical structure shown as in the chemical structure general formula (I), wherein R1, R2, R3 and R4 are selected from a, b, c or H, and R1, R2, R3 and R4 can not be H simultaneously; a refers to propionyl, butyryl or valeryl, b reters to various substituted benzoyl groups, and c refers to various substituted phenylsulfonyl groups. The invention also provides a preparation method and an application of the mangiferin aglycon derivative. The advantages are as follows: the compound has good blood glucose lowering effect whichis obviously superior to that of mangiferin and mangiferin aglycon, and the compound has no influence to blood glucose and blood fat of a normal rat and no toxic-side effect exist. The preparation method of the compound is convenient and feasible and has good repeatability and high compound yield; and with good officinal effect, the compound can be used for preparing drugs for treating diabetes mellitus and has wonderful development and utilization values. Formula (I).

Description

technical field [0001] The present invention relates to a kind of compound, specifically, a kind of mangiferin derivative and its preparation method and application. Background technique [0002] Mangiferin, also known as mangiferin and Zhimuning, is a natural polyphenol compound extracted from Liliaceae Anemarrhena, with molecular formula C 19 h 18 o 11 , molecular weight 422.33. Its chemical structure is as follows: [0003] [0004] The compound can also be extracted from the leaves, fruits, and bark of mango trees and almond trees in the Anacardiaceae family; Northeast Gentiana and Western Sichuan Swertia from the Gentianaceae plants; Modern pharmacology and clinical studies have proved that mangiferin has a variety of pharmacological effects: mangiferin has different pharmacological effects on the central nervous system, respiratory system, and cardiovascular system, as well as anti-radiation, anti-tumor, and anti-diabetic effects. Gallbladder effect, as well as...

Claims

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Application Information

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IPC IPC(8): C07D311/86A61K31/352A61P3/10
CPCC07D311/86A61P3/10
Inventor 韩军吴秋业陈万生
Owner SHANGHAI CHANGZHENG HOSPITAL
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