Acylated glycoside compounds as well as production method and application thereof

A technology of acylated glycosides and compounds, applied in the field of acylated glycosides compounds, can solve the problems of low bioavailability, poor gastrointestinal absorption of paeoniflorin and the like

Active Publication Date: 2012-08-22
NINGBO LIWAH PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The pharmacokinetic study of paeoniflorin showed that the gastrointestinal absorption of paeoniflorin is very poor, its bioavailability is very low, and it is eliminated rapidly.

Method used

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  • Acylated glycoside compounds as well as production method and application thereof
  • Acylated glycoside compounds as well as production method and application thereof
  • Acylated glycoside compounds as well as production method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, the synthesis of paeoniflorin tosylate

[0033] Accurately weigh 2g of paeoniflorin and dissolve it in pyridine (10ml), slowly add dichloromethane solution (5ml) containing p-toluenesulfonyl chloride (3.5g, 18mmol) dropwise in an ice-water bath, stir and react for 10h, then wash with 500ml of water Twice, and then extracted with 200ml ethyl acetate, the organic layer was taken and dried with an appropriate amount of anhydrous sodium sulfate. Let stand for a period of time, filter, and spin evaporate. Finally, it was recrystallized from absolute ethanol to obtain 0.51 g of a solid crude product in the form of light yellow powder, with a yield of 25.5%.

Embodiment 2

[0034] Embodiment 2, the purification of paeoniflorin tosylate

[0035] Accurately weigh 0.5 g of the crude product of paeoniflorin p-tosylate, dissolve with a small amount of eluent, and slowly load the sample on the silica gel column with a dropper (120 g of silica gel for column chromatography, the silica gel column is glass column, wet packed). Elute with dichloromethane-methanol (15:1, V / V), the amount of eluent depends on the separation effect, while controlling the flow rate, generally 5.0ml min -1 . Time tracking and identification by TLC method, 0.32g of paeoniflorin p-tosylate was obtained, the yield was 64.0%.

Embodiment 3

[0036] Embodiment 3, the synthesis of paeonifloride glycoside tosylate

[0037] Accurately weigh 0.5 g of paeonifloride and dissolve it in pyridine (8 ml), slowly add dropwise a dichloromethane solution (5 ml) containing p-toluenesulfonyl chloride (1 g, 9 mmol) in an ice-water bath, stir and react for 10 h, then use 100ml of water was washed twice, and then extracted with 100ml of ethyl acetate, and the organic layer was dried with an appropriate amount of anhydrous sodium sulfate. Let stand for a period of time, filter, and spin evaporate. Finally, it was recrystallized from absolute ethanol to obtain a light yellow powder solid crude product.

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Abstract

The invention provides acylated glycoside compounds as well as a production method and application thereof. The acylated glycoside compounds are characterized by comprising the following structural general formula: R1 is H, OH or OAc and R2 is toluenesulfonyl group and salicyl. The acylated glycoside compounds disclosed by the invention have an immune regulation function and can be used for preparing medicaments for treating rheumatoid arthritis, medicaments for treating autoimmune diseases such as systemic lupus erythematosus, eczema and parapsoriasis guttata as well as medicaments for treating various immunological diseases such as allergic reaction.

Description

technical field [0001] The invention relates to a class of acylated glycoside compounds, as well as a preparation method and application of the acylated glycoside compounds. Background technique [0002] Rheumatoid arthritis, systemic lupus erythematosus, eczema, psoriasis and other autoimmune diseases and allergies and other immune diseases are extremely harmful to humans. Total glucosides of paeony is a drug with definite curative effect on rheumatoid arthritis, and it can also be used to treat systemic lupus erythematosus, eczema, psoriasis, ankylosing spondylitis, etc. Pharmacological and clinical studies have found that total glucosides of paeony have multiple ways to inhibit autoimmune reactions, as well as anti-inflammatory, pain relief, liver protection and inhibition of autoimmunity and other pharmacological effects. The main medicinal components of total glucosides of paeony are a group of glycosides, including paeoniflorin, hydroxypaeoniflorin, paeoniflorin, paeo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04C07H1/06A61K31/7048A61P29/00A61P19/02A61P37/00A61P17/00A61P17/06A61P37/08
Inventor 周海滨江海龙傅旭春俞伟杨海玲徐军鲁俞江
Owner NINGBO LIWAH PHARM CO LTD
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