Berberine hydrochloride dimer as well as preparation method and application thereof

A technology of berberine hydrochloride and dimer, applied in the field of medicine, can solve the problems of less dimer, difficult synthesis of dimer, restricted compound research, etc., and achieves strong druggability, good antitumor activity, and great development value. Effect

Inactive Publication Date: 2021-09-21
PEKING UNIV SHENZHEN HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are very few studies on the dimers of berberine compounds at present, mainly because the dimers of berberine compounds are difficult to synthesize, which also limits further research on these compounds

Method used

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  • Berberine hydrochloride dimer as well as preparation method and application thereof
  • Berberine hydrochloride dimer as well as preparation method and application thereof
  • Berberine hydrochloride dimer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Take 371mg, 1mmol of berberine hydrochloride, dissolve it in 10mL of dichloromethane, add 430mg, 1mmol of [bis(trifluoroacetoxy) iodine]benzene, 282mg, 2mmol of boron trifluoride ether at -78°C, and react 4 hours, obtain reaction solution;

[0038] Use 60mL of ethyl acetate to extract the reaction solution, collect the organic phase, then dry the organic phase with sodium sulfate, filter and concentrate the organic phase, and then separate it through a silica gel column. The eluent is petroleum ether with a volume ratio of 3:1 to 1:1 Ethyl acetate mixture was separated to obtain 420 mg of the compound as a light yellow solid with a yield of 80 wt%.

Embodiment 2

[0040] The difference from Example 1 is that the reaction parameters are different.

[0041] Take 371mg, 1mmol of berberine hydrochloride, dissolve it in 10mL of tetrahydrofuran, and add 430mg, 1mmol of [bis(trifluoroacetoxy)iodo]benzene, 282mg, 2mmol of boron trifluoride ether at -78°C, and react for 4 hours , to obtain the reaction solution;

[0042] Use 60mL of ethyl acetate to extract the reaction solution, collect the organic phase, then dry the organic phase with sodium sulfate, filter and concentrate the organic phase, and then separate it through a silica gel column. The eluent is petroleum ether with a volume ratio of 3:1 to 1:1 Ethyl acetate mixture was separated to obtain 420 mg of the compound as a light yellow solid with a yield of 60 wt%.

Embodiment 3

[0044] The difference from Example 1 is that the reaction parameters are different.

[0045] Take 371mg, 1mmol of berberine hydrochloride, dissolve it in 10mL of dichloromethane, add 430mg, 1mmol of [bis(trifluoroacetoxy) iodine]benzene, 282mg, 2mmol of boron trifluoride ether at -30°C, and react 4 hours, obtain reaction solution;

[0046] Use 60mL of ethyl acetate to extract the reaction solution, collect the organic phase, then dry the organic phase with sodium sulfate, filter and concentrate the organic phase, and then separate it through a silica gel column. The eluent is petroleum ether with a volume ratio of 3:1 to 1:1. Ethyl acetate mixture was isolated to obtain 420 mg of the compound as a pale yellow solid, with a yield of 50 wt%.

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PUM

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Abstract

The invention provides a berberine hydrochloride dimer which has a chemical structure shown in the specification. The anti-tumor effect of the berberine hydrochloride dimer is remarkably superior to that of positive control berberine hydrochloride, and the berberine hydrochloride dimer has good anti-tumor activity and strong druggability; and as a novel anti-tumor compound, the compound has great development value. The invention also provides a preparation method of the berberine hydrochloride dimer.

Description

technical field [0001] The invention relates to the technical field of medicine, more specifically, to a berberine hydrochloride dimer and its preparation method and application. Background technique [0002] Medicinal chemistry research using natural products as lead compounds is playing an increasingly important role in promoting the development of modern medicine. Drugs related to natural products account for a considerable proportion of all kinds of drugs approved for marketing. According to statistics, the world Drugs related to natural products account for more than 50% of the approved marketed drugs. [0003] Therefore, using medicinal chemistry research methods to modify the structure of natural product monomer compounds is one of the important methods in the development of new drugs. [0004] Berberine hydrochloride is one of the main active ingredients in the heat-clearing traditional Chinese medicine Coptidis rhizome alkaloid extract. As an important traditional...

Claims

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Application Information

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IPC IPC(8): C07D455/03A61K31/4375A61P35/00
CPCC07D455/03A61P35/00
Inventor 陈健陶成王庆文林献张苗苗何莲花张楚楚
Owner PEKING UNIV SHENZHEN HOSPITAL
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