Long-chain alkyl coptisine halate derivative, synthesis method and application

The technology of a long-chain alkyl group and a synthesis method is applied in the field of derivatives of long-chain alkyl coptis base salts, and can solve problems such as no literature reports, and achieve a high blood lipid-lowering effect, which is beneficial to human body absorption and high in yield. Effect

Inactive Publication Date: 2010-07-28
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports in the literature about coptisine derivatives, especially 8-alkyl coptisine derivatives, and there are no reports in the literature about the hypoglycemic and blood lipid-lowering activities of 8-alkyl coptisine derivatives.

Method used

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  • Long-chain alkyl coptisine halate derivative, synthesis method and application
  • Long-chain alkyl coptisine halate derivative, synthesis method and application
  • Long-chain alkyl coptisine halate derivative, synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: 8-methyl coptisine iodate.

[0032]

[0033] It is prepared as follows:

[0034] ①. Dry all the reaction glass instruments, weigh 0.1mol of dried magnesium chips and place in a 250mL three-necked flask, use 40mL of anhydrous tetrahydrofuran as the reaction solvent, add 0.1mol of n-butane iodide under nitrogen protection, and prepare the corresponding Grignard reagent.

[0035] ②. Weigh 0.1 mol of dry berberine hydrochloride and put it in a 500mL three-neck flask, add 40mL of anhydrous tetrahydrofuran to make a suspension of berberine hydrochloride, and put it in an ice bath under nitrogen protection to -10°C.

[0036] ③. Slowly add the prepared Grignard reagent into the coptisine hydrochloride suspension under nitrogen protection and ice bath, while stirring. After the addition, remove the ice bath, return to room temperature, and heat to reflux for 2 hours to complete the reaction.

[0037] ④, centrifuge the reaction solution, take the supernatant, then...

Embodiment 2

[0040] Example 2: 8-butyl coptisine hydrochloride.

[0041]

[0042] It is prepared as follows:

[0043] ①. Dry all the reaction glass instruments, weigh 0.15mol of dried magnesium chips and place in a 250mL three-neck flask, use 40mL of anhydrous tetrahydrofuran as the reaction solvent, add 0.1mol of n-chlorobutane under nitrogen protection, and prepare the corresponding Grignard reagent.

[0044] ②. Weigh 0.01mol of dry berberine hydrochloride and place it in a 500mL three-neck flask, add 500mL of anhydrous tetrahydrofuran to make a suspension of berberine hydrochloride, and then place it in an ice bath under nitrogen protection to -10°C.

[0045] ③. Slowly add the prepared Grignard reagent into the coptisine hydrochloride suspension under nitrogen protection and ice bath, while stirring. After the addition, remove the ice bath, return to room temperature, and heat to reflux for 2 hours to complete the reaction.

[0046] ④, centrifuge the reaction solution, take the sup...

Embodiment 3

[0049] Example 3: 8-octyl coptisine bromate.

[0050]

[0051] It is prepared as follows:

[0052] ①. Dry all the reaction glass instruments, weigh 0.13mol of dried magnesium chips and place in a 250mL three-necked flask, use 40mL of anhydrous tetrahydrofuran as the reaction solvent, add 0.1mol of brominated n-octane under nitrogen protection, and prepare the corresponding Grignard reagent.

[0053] ②. Weigh 0.05mol of dry berberine hydrochloride and place it in a 500mL three-necked flask, add 1000mL of anhydrous tetrahydrofuran to form a berberine hydrochloride suspension, and then place it in an ice bath under nitrogen protection to -10°C.

[0054] ③. Slowly add the prepared Grignard reagent to the Coptis base suspension under nitrogen protection and ice bath, while stirring, remove the ice bath after the addition, return to room temperature, and heat to reflux for 2 hours to complete the reaction.

[0055] ④, centrifuge the reaction solution, take the supernatant, then...

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PUM

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Abstract

The invention relates to a new chemical substance with a chemical name of long-chain alkyl coptisine halate derivative (hydrochloride or bromate or iodate or hydrofluoride). The molecular structural formula of the derivative is disclosed in the specification, wherein X is F-, Cl-, Br- and I-; and R is CnH2n+1, and n is 1-20. The substance has obvious activity of reducing the blood fat and the blood sugar, and the activity of reducing the blood fat and the blood sugar is obviously higher than that of the coptisine salt, thus the long-chain alkyl coptisine halate derivative is a promising new compound having medicinal values of blood fat reduction, blood sugar reduction, and the like.

Description

technical field [0001] The present invention relates to a class of novel compounds and their medical applications, in particular to a derivative of long-chain alkyl berberine salt. Background technique [0002] Coptisine (Coptisine) is one of the main alkaloids in Coptis chinensis, and it is also the main active ingredient of Coptis chinensis. There are few studies on the biological activity of coptisine. Zheng Hongyan and others have reported the antibacterial and hypoglycemic biological activities of coptisine (Zheng Hongyan, master's degree thesis of Tianjin Medical University, 2004). However, there are no reports in the literature about coptisine derivatives, especially 8-alkyl coptisine derivatives, and there is no literature report about the hypoglycemic and blood lipid-lowering activities of 8-alkyl coptisine derivatives. Contents of the invention [0003] The object of the present invention is to propose long-chain alkyl coptisine salt derivatives, disclose its pu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22A61K31/4745A61P3/06A61P3/10
Inventor 李学刚叶小利
Owner SOUTHWEST UNIVERSITY
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