Paeoniflorin aromatic ester derivative, preparation method and applications thereof

A technology for paeoniflorin and derivatives, which is applied in the field of paeoniflorin derivatives and achieves the effects of high yield, mild technical route conditions and improved bioavailability

Active Publication Date: 2012-07-25
GUANGZHOU HANFANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention aims to provide a paeoniflorin aromatic ester derivative, its preparation method and its use. The technical problem to be solved is to select a suitable structure to make paeoniflorin have strong lipophilicity, thereby increasing the bioavailability of paeoniflorin , improve its efficacy and reduce its adverse reactions

Method used

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  • Paeoniflorin aromatic ester derivative, preparation method and applications thereof
  • Paeoniflorin aromatic ester derivative, preparation method and applications thereof
  • Paeoniflorin aromatic ester derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In a 500ml three-necked flask equipped with an electromagnetic stirrer and a thermometer, 3g of paeoniflorin, 60ml of pyridine, 60ml of chloroform, and 76mg of dimethylaminopyridine were sequentially added. At room temperature (25°C), within 4 hours, slowly add benzoyl chloride solution (604ul benzoyl chloride dissolved in 30ml of chloroform) dropwise to the three-necked flask, after the dropwise addition, continue to stir for 8 hours, the reaction Finish. The reaction solution was washed three times with 120ml (40ml×3) of water, and the organic layer was dried over anhydrous sodium sulfate and filtered. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: trichloromethane:methanol=35:1) to obtain pure benzoylpaeoniflorin as a white crystalline solid with a yield of 45%.

[0035] 1 HNMR (DMSO): δ (ppm):

[0036] 1.34 (3H, s, 10-H), 1.80 (1H, d, J = 12.5Hz, 3α-H), 1.93 (1H, d, J = 10.8Hz, 7α-H), 2.10 (1H, ...

Embodiment 2

[0042] In a 500ml three-neck flask equipped with an electromagnetic stirrer and a thermometer, add 3g of paeoniflorin, 45ml of pyridine, 150ml of chloroform, and 120mg of dipropylaminopyridine in sequence, and at room temperature (25°C) within 4 hours, the benzyl The acid anhydride solution (1.2ml of benzoic anhydride dissolved in 120ml of chloroform) was slowly added dropwise into the three-neck flask, and after the dropwise addition was completed, the stirring was continued for 4 hours, and the reaction was completed. The reaction solution was washed three times with 120ml (40ml×3) of water, and the organic layer was dried over anhydrous sodium sulfate and filtered. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: trichloromethane:methanol=40:1) to obtain pure benzoylpaeoniflorin as a white crystalline solid with a yield of 37%.

[0043] 1 HNMR (DMSO): δ (ppm):

[0044] 1.34 (3H, s, 10-H), 1.80 (1H, d, J = ...

Embodiment 3

[0050] In a 500ml three-necked flask equipped with an electromagnetic stirrer and a thermometer, 3g of paeoniflorin, 90ml of pyridine, and 114mg of dimethylaminopyridine were sequentially added. Slowly add the benzenesulfonyl chloride solution (1.5ml of benzenesulfonyl chloride dissolved in 100ml of methylene chloride) dropwise into the three-necked flask at 35°C within 4 hours. After the dropwise addition, continue stirring for 20 hours to complete the reaction. The reaction solution was washed three times with 120ml (40ml×3) of water, and the organic layer was dried over anhydrous sodium sulfate and filtered. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: chloroform: methanol = 25:1) to obtain pure benzenesulfonyl paeoniflorin as a white crystalline solid with a yield of 41%.

[0051] 1 HNMR (DMSO): δ (ppm):

[0052] 1.14 (3H, s, 10-H), 1.66 (1H, d, J = 12.5Hz, 3α-H), 1.69 (1H, d, J = 10.8Hz, 7α-H), 1.91 ...

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Abstract

The invention discloses a paeoniflorin aromatic ester derivative, a preparation method and applications of the paeoniflorin aromatic ester derivative. The general structure formula of the paeoniflorin aromatic ester derivative is as follows: in the formula, R is selected from benzoyl, phenylsulfonyl, phenylacetyl, benzene propionyl, benzene acryloyl, p-chlorobenzoyl, 3, 5-dimethoxybenzoyl, 2-( acetoxyl group) benzoyl, 2-methyl-4-(2'-methyl propyl) phenylacetyl or 2-[(2', 6-dichlorophenyl) amino]- phenylacetyl. The preparation method comprises the steps of taking paeoniflorin as raw materials, conducting esterification on the paeoniflorin in a solvent through aromatic acyl chloride or aromatic anhydride, then conducting washing and column chromatography to obtain the paeoniflorin aromatic ester derivative. The paeoniflorin aromatic ester derivative has the advantages that the bioavailability of the paeoniflorin is improved and the anti-inflammatory action is strong, and can be made into injection, tablets, capsules, dropping pills and particles for treating chronic infectious arthritis.

Description

1. Technical field [0001] The invention relates to a paeoniflorin derivative, specifically a paeoniflorin aromatic ester derivative, a preparation method and application thereof. 2. Background technology [0002] Rheumatoid arthritis (RA) is a common chronic autoimmune disease with synovial inflammation as the main pathological manifestation. The salient feature of RA is the angiogenesis and inflammatory cell infiltration of the synovium, which can further lead to the destruction of the synovium, cartilage, and even subchondral bone tissue. Deformation and loss of function, 1 / 3 of the patients can become disabled, seriously affecting human health and quality of life. [0003] Total glucosides of paeony (TGP) is an effective part extracted from the traditional Chinese medicine Radix Paeoniae Alba, and it has been officially approved for production and marketing as the first anti-inflammatory and immunomodulatory drug. Paeoniflorin (Pae), as one of the main active ingredient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04C07H1/00A61K31/7048A61P29/00A61P19/02
Inventor 魏伟王春
Owner GUANGZHOU HANFANG PHARMA
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