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Glycoside class compound of mango, preparation method, and application in area of medicine

A compound, the technology of mangiferin, which is applied in the field of mangiferin compounds, can solve the problems of poor solubility and limitations

Inactive Publication Date: 2007-07-25
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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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. Therefore, we synthesized a series of mangiferin compounds with mangiferin as the lead compound, and then screened the prepared compounds for PTP1B inhibitory activity in order to find out highly active compound
At present, there are no such research reports at home and abroad

Method used

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  • Glycoside class compound of mango, preparation method, and application in area of medicine
  • Glycoside class compound of mango, preparation method, and application in area of medicine
  • Glycoside class compound of mango, preparation method, and application in area of medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Prepare the compound according to the above method, light yellow crystal; yield: 56.3%; melting point: 170~172°C; IR(KBr)cm 1 : 3430, 2972, 2934, 2879, 1648, 1606, 1468, 1381, 1278, 1198, 1090, 1028, 905, 811, 791, 657, 578; 1 HNMR (DMSO-d 6, δ): 13.50(1H, s), 7.50(1H, s), 7.16(1H, s), 6.61(1H, s), 4.83(2H, b), 4.63(1H, m), 4.60~4.55( 2H, m), 4.54 (1H, b), 4.36 (1H, b), 4.28 (1H, m), 4.04 (1H, m), 3.75~3.66 (2H, m), 3.18 (2H, m), 3.05 (1H, m), 1.77-1.61 (6H, m), 1.34-1.24 (9H, m), 1.05-0.93 (9H, m).

Embodiment 2

[0027] Example 2: Synthesis of 2-C-β-D-glucopyranosyl-3,6,7-tri(1-heptyl)-1-hydroxyl-xanthone (compound 6 in Table 1)

[0028] Prepare the compound according to the above method, light yellow crystal; yield: 66.2%; melting point: 122~123°C; IR(KBr)cm -1 : 3438, 2928, 2856, 1648, 1609, 1580, 1507, 1466, 1394, 1277, 1226, 1200, 1111, 1085, 1030, 901, 823, 807, 724, 661, 632, 576; 1 HNMR (DMSO-d 6 , δ): 13.48(1H, s), 7.46(1H, s), 7.07(1H, s), 6.55(1H, s), 4.69(2H, b), 4.63(1H, m), 4.31(1H, b), 4.15(1H,b), 4.07(6H,m), 4.05(1H,m), 3.74(1H,m), 3.45(1H,m), 3.23(2H,m), 3.15(1H,m ), 1.78 (6H, m), 1.47 (6H, m), 1.31 (18H, m), 0.89 (9H, m).

Embodiment 3

[0029] Example 3: Synthesis of 2-C-β-D-glucopyranosyl-3,6,7-tribenzyl-1-hydroxyl-xanthone (compound 11 in Table 1)

[0030] Prepare the compound according to the above method, light yellow crystal; yield: 54.4%; melting point: 133~134°C; IR(KBr)cm 1 : 3413, 3062, 3031, 2874, 1646, 1609, 1581, 1500, 1475, 1391, 1278, 1223, 1188, 1082, 1025, 905, 809, 737, 696, 668, 642, 615, 571, 466; 1 HNMR (DMSO-d 6 , δ): 13.48(1H, s), 7.63~7.29(17H, m), 6.75(1H, s), 5.29(2H, s), 5.22~5.14(4H, m), 4.70(1H, dd), 4.00(1H,t), 3.67(1H,m), 3.45(1H,m), 3.41(4H,b), 3.22(2H,m), 3.10(1H,m).

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PUM

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Abstract

This invention discloses compounds with natural product mangiferin as the frame. The general chemical structure of the compounds is shown in formula I, wherein, R1 and R2 are C1-20 linear or branched alkyl, benzyl, or substituted benzyl. The substituent is halogen, alkyl, etc. The compounds have strong inhibitive activity on protein tyrosine phosphatase 1B (PTP1B). This invention also discloses a method for preparing the compounds. The compounds can be used to treat diseases related to PTP1B inhibition, including diabetes type 2.

Description

technical field [0001] The invention relates to a mangiferin compound, a preparation method thereof and an application in the field of medicine. Background technique [0002] Mangiferin, also known as mangiferin and Zhimuning, is a natural polyphenol compound extracted from Liliaceae Anemarrhena, molecular formula: C 19 h 18 o 11 , molecular weight: 422. 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 of Anacardiaceae; Northeast Gentiana and Western Sichuan Swert of Gentianaceae; Guangshiwei, a plant of Water Keelaceae. 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 anti-inflam...

Claims

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Application Information

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IPC IPC(8): C07H17/04A61K31/7048A61P3/10
Inventor 吴秋业陈万生胡宏岗赵庆杰廖洪利徐建明张大志俞世冲蔡灵芝金永生孙青䶮
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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