Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Kutkin derivative, preparation method and application thereof

A technology of berberine and derivatives, applied in the field of berberine derivatives and preparation thereof, can solve problems such as side effects in the gastrointestinal tract, and achieve the effects of no toxic and side effects, low cost and simple preparation process

Active Publication Date: 2010-01-27
JINAN UNIVERSITY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The existing anti-arthritic drugs are mainly non-steroidal anti-inflammatory drugs, however, long-term use of such drugs often produces gastrointestinal side effects
These drugs have been shown to cause cartilage damage in animal experiments and are not effective for ankle arthritis

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Kutkin derivative, preparation method and application thereof
  • Kutkin derivative, preparation method and application thereof
  • Kutkin derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0026] The synthesis of embodiment 14-acetoxy-3-methoxybenzophenone

[0027] Acetyl chloride (1.28ml, 18mmol) was added dropwise to berberine (2g, 12mmol) 20ml ethyl acetate solution cooled to 0°C, and triethylamine was added dropwise under nitrogen, and the reaction solution was gradually warming up to room temperature and stirred for 2 hours. The reactant was washed 3 times with water (50mlx3), the organic layer was dried with anhydrous sodium sulfate, and recrystallized with ethyl acetate to obtain 1.8g of white crystals with a yield of 72%. mp 56-57°C. 1 H NMR (acetone-d 6 , ppm): 7.67-7.56 (m, 2H, Ar-H), 7.21-7.13 (d, 1H, Ar-H), 3.88 (s, 3H, OCH 3 ), 2.57 (s, 3H, COCH 3 ), 2.27 (s, 3H, O COCH 3 ), the molecular formula of MS 208. product 4-acetoxy-3-methoxybenzophenone is as follows:

[0028]

Embodiment 24

[0029] The synthesis of embodiment 24-hydroxyl-3-methoxyl group-5-nitrobenzophenone

[0030] In berberine (10.2g, 61mmol) 500ml chloroform solution, concentrated nitric acid (70%, 16.3ml) was added dropwise at 0°C, the reaction solution was kept stirring for 2 hours, the reaction solution was washed 7 times with water (70mlx7), and the organic layer was washed with water for 7 times (70mlx7). Dry over anhydrous sodium sulfate, remove the solvent under reduced pressure, add 250ml of 95% ethanol, and crystallize overnight to obtain 9.5g of a yellow needle-like product with a yield of 73%. mp 159-161℃. 1 H NMR (CDCl 3 , ppm): 11.13 (s, 1H, OH), 8.32-8.31 (d, 1H, Ar-H), 7.78-7.77 (d, 1H, Ar-H), 4.02 (s, 3H, OCH 3 ), 2.64 (s, 3H, COCH 3 ), MS 211.

[0031] The molecular formula of product 4-hydroxyl-3-methoxyl group-5-nitrobenzophenone is as follows:

[0032]

Embodiment 35

[0033] Synthesis of Example 35-amino-4-hydroxyl-3-methoxy-benzophenone

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a derivant of kutkin with chemical structural formula as formula I, wherein R1 is NO2, NH2 or amide; R2 is H, carbonyl or diaminocarbonyl. The preparing method comprises the following steps: nitrating kutkin to obtain kutkin derivant substituted by nitro group or kutkin derivant based on substituted nitro group; or kutkin derivant substituted by acetylamino.

Description

technical field [0001] The invention relates to berberine derivatives and a preparation method thereof. [0002] The present invention also relates to the application of the berberine derivatives in pharmacy. Background technique [0003] Arthritis (RA for short, the same below) is a chronic damaging immune disease that can damage synovial tissue and extra-articular tissues. Immune particles accumulate in the synovium, causing damage to joint tissue in RA patients. The end result of RA is a spectrum of pain, mobility difficulties, functional impairment and rheumatoid disease. [0004] The existing anti-arthritic drugs are mainly non-steroidal anti-inflammatory drugs, however, long-term use of such drugs often produces gastrointestinal side effects. These drugs have been shown to cause cartilage damage in animal experiments and are not effective for ankle arthritis. [0005] The traditional Chinese medicine Huhuanglian is the dried rhizome of Huhuanglian, a perennial herb...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/035C07C205/45C07C225/20C07C233/33A61K31/22A61K31/165A61K31/136A61P19/04A61P19/02A61P37/02
Inventor 蒋杰杨兆棋张在军李沙王玉强
Owner JINAN UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com