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Synthetic method of berberine 13-bit derivant and berberrubine 13-bit derivant

A technology of berberine and synthesis method, which can be applied in the directions of antifungal agents, organic chemistry, antibacterial drugs, etc., and can solve the problems of reducing activity and the like

Inactive Publication Date: 2011-09-28
CHANGCHUN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Kim et al [2] Comparing the effects of berberine 9-acyloxy and 9-alkoxy substitutions on antibacterial activity, it was found that alkoxy analogs had stronger antibacterial activity than acyloxy analogs, too long or too short substituents will reduce the activity

Method used

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  • Synthetic method of berberine 13-bit derivant and berberrubine 13-bit derivant
  • Synthetic method of berberine 13-bit derivant and berberrubine 13-bit derivant
  • Synthetic method of berberine 13-bit derivant and berberrubine 13-bit derivant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: Preparation of 8-acetyl berberine

[0047] Weigh 0.5g of berberine into a 50ml three-neck flask, add 20ml of sodium hydroxide solution with a molar concentration of 1mol / L to dissolve it completely, slowly add 0.11mL of acetone dropwise at a rate of 0.17ml / min, and place at 24°C The reaction was stirred for 4 hours to obtain 0.25 g of 8-acetyl berberine. The yield was 42%.

Embodiment 2

[0048] Embodiment 2: Preparation of 8-acetyl berberine

[0049] Weigh 0.5g of berberine into a 50mL three-neck bottle, add 20mL of sodium hydroxide solution with a molar concentration of 4mol / L to dissolve it completely, slowly add 0.33mL of acetone dropwise at a rate of 0.17ml / min, and store at 24°C The reaction was stirred for 4 hours to obtain 0.49 g of 8-acetyl berberine. The yield was 84%.

Embodiment 3

[0050] Embodiment 3: the preparation of 8-acetyl berberine

[0051] Weigh 0.5g of berberine into a 50mL three-necked bottle, add 20mL of sodium hydroxide solution with a molar concentration of 7mol / L to dissolve it completely, slowly add 0.55ml of acetone dropwise at a rate of 0.17ml / min, and stir at 24°C After reacting for 4 hours, 0.39 g of 8-acetyl berberine was obtained. The yield is 67%.

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Abstract

The invention provides a synthetic method of a berberine 13-bit derivant and a berberrubine 13-bit derivant. The synthetic method is used to prepare derivants as follows: 13-benzyl berberine, 13-(2', 4'-binitro) benzyl berberine, 13-benzyl berberrubine and 13-(2', 4'-binitro) benzyl berberrubine, which show excellent inhibiting effect on gram-positive bacterium, wherein the value of minimal inhibitory concentration (MIC) of the berberine is 64mug / ml, the value of MIC of the berberrubine is larger then 128mug / ml, the values of MIC of the 13-benzyl berberine, the 13-(2',4'-binitro) benzyl berberine, the 13-benzyl berberrubine and the 13-(2',4'-binitro) benzyl berberrubine are respectively 32mug / ml, 16mug / ml, 32mug / ml and 8mug / ml. The synthetized derivants, the antimicrobial activity of which is better than matrixes, can be used as raw materials of antimicrobial drugs.

Description

technical field [0001] The invention relates to a synthesis method of a 13-position berberine derivative and a 13-position berberine derivative. Background technique [0002] The following infectious diseases caused by Gram-positive bacteria: urinary system infection: acute urethritis, acute pyelitis, prostatitis, etc.; tonsillitis, suppurative otitis media, sinusitis, etc.; acute bronchitis, chronic bronchitis attack, Pneumonia, lung abscess and bronchiectasis with infection. Most pyogenes are Gram-positive bacteria that can produce exotoxins to make people sick. Common Gram-positive bacteria are: Staphylococcus, Streptococcus, Diplococcus pneumoniae, Bacillus anthracis, Bacillus diphtheria, Bacillus tetani, etc. [0003] Berberine, also known as berberine, is an antibacterial alkaloid derived from raw materials such as Coptis chinensis and Phellodendron amurense. Its hydrochloride is a yellow powder with a bitter taste and slightly soluble in water. It can kill Shigella...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D455/03A61P31/04A61P31/10
Inventor 王道武邵凯张龙
Owner CHANGCHUN UNIV OF TECH
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