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14-hydroxyl sinomenine derivatives, synthesis method thereof and use thereof

A technology of hydroxysinomenine and derivatives, applied in the field of compounds, can solve the problems of slow onset, low bioavailability, weak action intensity and the like

Inactive Publication Date: 2010-01-20
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Rheumatoid arthritis is a chronic disease that endangers human health. Although sinomenine has achieved certain effects in the treatment of rheumatoid arthritis in the form of combined medication, its action strength is weak, its onset is slow, and its bioavailability is low. Sinomenine derivatives with higher efficacy and better pharmacokinetic properties have important application significance

Method used

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  • 14-hydroxyl sinomenine derivatives, synthesis method thereof and use thereof
  • 14-hydroxyl sinomenine derivatives, synthesis method thereof and use thereof
  • 14-hydroxyl sinomenine derivatives, synthesis method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 14-Hydroxy-O-methylsinomenine (Compound 1)

[0042] 0.5g O-methyl sinomenine was dissolved in 30mL dichloromethane, and 5g active MnO was added in batches 2 , warming up to reflux for 42h. Cool to room temperature, filter, and concentrate the filtrate to obtain a crude product, which is separated by silica gel column chromatography (eluent: ethyl acetate) to obtain compound 1, yield: 13%, mp: 157.3-157.5°C.

Embodiment 2

[0044] 6,14-Dihydroxy-O-methyl sinomenine (Compound 2)

[0045] Dissolve 0.3g of 14-hydroxy-O-methylsinomenine in 10mL of anhydrous methanol, cool to 0°C in an ice-water bath, add 0.3g of NaBH 4 , warmed to room temperature and stirred for 2h, concentrated the reactant, and added 10mL of water and 0.3g of NH to the obtained solid 4 Cl, stirred at room temperature for 15 min, extracted with 2×20 mL of dichloromethane, combined organic layers, and dried over anhydrous sodium sulfate. The residue after removing the solvent under reduced pressure was separated by silica gel column chromatography (eluent: ethyl acetate) to obtain compound 2, yield: 88%, mp: 167.2-169.0°C.

Embodiment 3

[0047] 14-Acetoxy-O-methyl sinomenine (Compound 3)

[0048] Mix 0.5g 14-hydroxy-O-methyl sinomenine, 20mL dichloromethane and 1mL acetic anhydride, start to stir, reflux for 2h, cool, spin off the solvent under reduced pressure, pack the column with silica gel chromatography, and then wash with ethyl acetate , and 20:1 chloroform / methanol eluting to obtain compound 3, yield: 78%, mp: 149.5-152.1°C.

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Abstract

The invention discloses 14-hydroxyl sinomenine derivatives, a preparation method thereof and anti-inflammatory activity thereof. The 14-hydroxyl sinomenine derivatives are prepared from the raw materials of O-alkyl sinomenine and O-acyl sinomenine by a chemical method that reactions such as oxidation and hydroxylation are carried out at a 14-position. The compounds of the invention show excellent anti-inflammatory activity in in-vivo tests of animals and have an excellent application prospect.

Description

technical field [0001] The present invention relates to a class of compounds, preparation methods and medicinal uses, in particular to a class of 14-hydroxysinomenine derivatives, a chemical synthesis method for the compounds, and the compounds provided by the invention have anti-inflammatory activity. Background technique [0002] Sinomenine (sinomenine) is an alkaloid extracted from the rhizomes of the plants of the family Fangfengceae, Qingfengteng and Ivy. According to records, sinomenine has biological activities such as anti-inflammatory, analgesic, antihypertensive, and antiarrhythmic, and is mainly used in the treatment of diseases such as rheumatoid arthritis and arrhythmia clinically (Wang Naiqin et al. Acta Pharmaceutica Sinica, 1992, 23 (2) 81; Editor-in-Chief Zhou Jinhuang et al. Advances in Pharmacology and Clinical Research of Traditional Chinese Medicine, Volume II, Beijing: China Science and Technology Press, 1993.). [0003] After the 1990s, the research o...

Claims

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Application Information

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IPC IPC(8): C07D221/28A61K31/485A61P29/00
Inventor 李玉峰朱红军钱溢宋广亮王锦堂
Owner NANJING UNIV OF TECH
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