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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, simple preparation process and low cost

Active Publication Date: 2007-03-07
JINAN UNIVERSITY
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  • 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

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  • 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 1

[0025] The synthesis of embodiment 1 4-acetoxy-3-methoxyacetophenone

[0026] 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 (50ml×3), 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, OCOCH 3 ), MS 208.

[0027] The molecular formula of product 4-acetoxy-3-methoxyacetophenone is as follows:

[0028]

Embodiment 2

[0029] Example 2 Synthesis of 4-hydroxyl-3-methoxyl group-5-nitroacetophenone

[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-nitroacetophenone is as follows:

[0032]

Embodiment 3

[0033] Example 3 Synthesis of 5-amino-4-hydroxyl-3-methoxy-acetophenone

[0034] In embodiment 2 product (2g, 9.5mmol) ethyl acetate solution, add 10%Pd / C (200mg), reaction solution is at 40lb / inch 2 Hydrogenate for 1 hour, filter, remove the solvent, add concentrated hydrochloric acid, filter the precipitate, and recrystallize with ethanol to obtain 1.1 g of colorless crystals, with a yield of 53%. 1 H NMR (D 2 O, ppm): 7.57-7.55 (d, 1H, Ar-H), 7.45-7.43 (d, 1H, Ar-H), 3.88 (s, 3H, OCH 3 ), 2.55(s, 3H, COCH 3 ), MS 181.

[0035] The molecular formula of product 5-amino-4-hydroxyl-3-methoxy-acetophenone is as follows:

[0036]

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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

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Application Information

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Patent Type & Authority Applications(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
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