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Hongjingtian glycoside derivative and its preparation method and use

A salidroside and derivative technology, applied in the field of medicine, can solve the problems of low total yield, cumbersome reaction operation, and easy pollution of the environment, and achieve the effects of increasing yield, reducing cost, and reducing pollution

Inactive Publication Date: 2004-02-18
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The defect of this synthetic method is that the reaction operation is loaded down with trivial details, and the solvent that adopts the big toxicity such as benzene is easy to pollute the environment; Adopt expensive reagents such as Pd-C lithium aluminum hydride to make cost higher; And yield is low, and total yield is all lower than 50 %, [Li Guoqing, Li Zhan. Improvement of the Synthetic Method of Salidroside. Chinese Journal of Medicinal Chemistry, 1996, 6 (2); Zhang Sanqi, Shang Gangwei, Li Zhongjun, etc. A New Way to Synthesize Salidroside. Chinese Medicine Journal of Chemistry, 1997, 7(4); Zhang Lianji, Li Xuemei, Tian Guanrong. Synthesis of salidroside. Journal of Yanbian University (Natural Science Edition), 2002, 28(2)]

Method used

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  • Hongjingtian glycoside derivative and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Now in conjunction with the examples, the preparation method of the compound of the present invention is described in detail. Example 1: Preparation of 1-(4-hydroxy)phenethyl-β-D-glucopyranoside (salidroside, Compound No. 1).

[0046] Nitrogen was passed into a 50ml round bottom flask for protection, 30ml of anhydrous dichloromethane, 1g (7.5mmol) of 4-hydroxyphenethyl alcohol, 1.65g (6mmol) of silver carbonate were added, and the reaction was carried out at room temperature for 30 minutes in the dark under stirring . Add 2.65 g (6.5 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-bromoglucopyranose and 0.83 g (3 mmol) of silver carbonate, and react at room temperature for 24 hours. After filtration, the solvent was distilled off under reduced pressure to obtain a viscous colorless residue, which is 1-(4-hydroxy)phenylethyl-β-D-glucopyranoside acetylated with sugar hydroxy groups.

[0047] Add 20ml (27mM) of methanol solution dissolved with sodium methoxide to the above residue, ...

Embodiment 2

[0048] Example 2: Preparation of 1-(4-hydroxy)phenethyl-β-D-galactopyranoside (Compound No. 17).

[0049] Nitrogen was passed into a 50ml round bottom flask, 30ml of anhydrous dichloromethane, 1g (7.5mmol) of 4-hydroxyphenethyl alcohol, 1.65g (6mmol) of silver carbonate were added, and the reaction was carried out at room temperature in the dark for 30 minutes under stirring, and then added 2.65 g (6.5 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-bromogalactopyranose and 0.83 g (3 mmol) of silver carbonate were reacted at room temperature for 24 hours. After filtration, the solvent was distilled off under reduced pressure to obtain a viscous colorless liquid, which was 1-(4-hydroxy)phenethyl-β-D-galactopyranoside acetylated with sugar hydroxy groups.

[0050] Add 20ml (27mM) of methanol solution dissolved with sodium methoxide into the above solution, react at room temperature for 20 hours, concentrate under reduced pressure, separate with silica gel G column chromatography, and use ch...

Embodiment 3

[0051] Example 3: Preparation of 1-(3-hydroxy)phenethyl-β-D-glucopyranoside (Compound No. 2).

[0052] Nitrogen was passed into a 50ml round bottom flask, 30ml of anhydrous dichloromethane, 1g (7.5mmol) of 3-hydroxyphenethyl alcohol, 1.65g (6mmol) of silver carbonate were added, and the reaction was carried out at room temperature in the dark for 30 minutes under stirring, and then added 2,3,4,6-Tetra-O-acetyl-α-D-bromoglucopyranose 2.65g (6.5mmol), silver carbonate 0.83g (3mmol), react at room temperature for 24 hours, filter, evaporate under reduced pressure Solvent, a viscous colorless residue was obtained, which was sugar hydroxyacetylated 1-(3-hydroxy)phenethyl-β-D-glucopyranoside.

[0053] Add 20ml (27mM) of methanol solution dissolved with sodium methoxide to the above residue, react at room temperature for 20 hours, concentrate under reduced pressure, separate with silica gel G column chromatography, use chloroform and methanol (4:1) as developing solvent, and obtain t...

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Abstract

A salidroside derivative is disclosed, which can be used to prepare the antioxidizing medicines. Its preparing process is also disclosed, which features simple process, high output rate, low cost andless environmental pollution.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to salidroside series derivatives, a preparation method of salidroside and the derivatives thereof, and the use of the salidroside derivatives for preparing antioxidant drugs. Background technique [0002] Salidroside, English name salidroside, chemical name "p-hydroxyphenethyl-β-D-glucopyranoside (p-hydroxyphenethyl-β-D-glucos ide)", systematic name: 1-(4-hydroxyl) Phenylethyl-β-D-glucopyranoside is an active compound extracted from medicinal plants, mainly from the plateau medicinal plant "Rhodiola sachalinensis" and the commonly used traditional Chinese medicine "Ligustrum lucidum" (Ligustrum lucidum) extracted from. [Xu Baojun, Zheng Yinan, Li Xianggao. New progress in the research of Rhodiola plants. Chinese Medicinal Materials, 2000, 23(9); Shi Lifu, Cai Qin, Cao Yingying, etc. Chemical constituents and pharmacological effects of the traditional Chinese medicine Ligustrum luci...

Claims

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Application Information

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IPC IPC(8): A61K31/7028A61P39/06C07H15/18
Inventor 石力夫蔡溱姚斌
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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