8-octyl berberine hydrochloride and its synthesis process and application

A technology of berberine salt and berberine hydrochloride, which is applied in the directions of medical preparations, drug combinations, and pharmaceutical formulations containing active ingredients, can solve the problem that the 8-position of berberine is not yet connected to a long-chain alkyl group, 8 -The synthesis of alkyl berberine salts has no problems such as reports, and achieves the effects of good development and utilization value, low price and high yield

Inactive Publication Date: 2007-06-06
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there have been no derivatives with long-chain alkyl attached to the 8-position of berberine (such as the report of berberine hydrochloride derivatives above octyl)
[0003] So far, there are research reports on the synthesis of substances such as berberine salt, 8-ethyl berberine salt, 8-butyl berberine salt, and 8-hexyl berberine salt, but for 8-octyl berberine The synthesis of berberine salts and 8-alkyl berberine salts with longer carbon chains has not been reported yet
In addition, there have been research reports on the antibacterial activity of substances such as berberine salt, 8-ethylberberine salt, 8-butylberberine salt, and 8-hexylberberine salt. and hypoglycemic activity have not been reported; there is no report on the hypolipidemic and hypoglycemic activity of 8-octyl berberine salt

Method used

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  • 8-octyl berberine hydrochloride and its synthesis process and application
  • 8-octyl berberine hydrochloride and its synthesis process and application

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Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1: Preparation of 8-octylberberine hydrochloride

[0036] ①. Dry all 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-octane chloride under nitrogen protection, and prepare the corresponding Grignard reagent.

[0037] ②. Weigh 0.1mol of dry berberine hydrochloride and place it in a 500mL three-neck flask, add 100mL of anhydrous tetrahydrofuran to make a suspension of berberine hydrochloride, and then place it in an ice bath to -10°C under nitrogen protection.

[0038] ③. Slowly add the prepared Grignard reagent to the berberine 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.

[0039] ④, centrifuge the reaction solution, take the supernatant, then add tetrahydrofuran to extract, rep...

Embodiment 2

[0043] ①. Dry all reaction glass instruments, weigh 0.12mol of dried magnesium chips and place in a 250mL three-necked flask, use 100mL of anhydrous ether as the reaction solvent, add 0.06mol of n-bromodecane under nitrogen protection, and prepare the corresponding Grignard reagent.

[0044] ②. Weigh 0.03mol of dry berberine hydrochloride and place it in a 500mL three-neck flask, add 100mL of anhydrous ether to form a suspension of berberine hydrochloride, and then ice-bath to 0°C under nitrogen protection.

[0045] ③. Slowly add the prepared Grignard reagent to the berberine 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 supernatant, then add diethyl ether to extract, repeat several times, monitor the extraction situation of the reaction product with the thin layer method, until...

Embodiment 3

[0050] ①. Dry all reaction glass instruments, weigh 0.12mol of dried magnesium chips and place in a 250mL three-neck flask, use 150mL of dioxane as the reaction solvent, add 0.1mol of n-dodecane iodide under nitrogen protection, Prepare the corresponding Grignard reagents.

[0051] ②. Weigh 0.05mol of dry berberine hydrochloride and place it in a 500mL three-necked flask, add 100mL of dioxane to form a suspension of berberine hydrochloride, and then ice-bath to 10°C under nitrogen protection.

[0052] ③. Slowly add the prepared Grignard reagent to the berberine 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.

[0053] ④, centrifuge the reaction solution, take the supernatant, then add dioxane to extract, repeat several times, monitor the extraction situation of the reaction product with the thin layer method, until the raw material poi...

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Abstract

The present invention relates to one new kind of compound, named chemically as 8-octyl berberine salt (hydrochloride, bromide, iodide or hydrofluoride). The compound has the molecular expression of C28H34O4N .X, where, X is F-, Cl-, Br-, I- or other anion, and the structural formula as shown. Compound 8-octyl berberine salt has antibacterial activity, antilipemic activity and hypoglycemic activity obviously higher than that of berberine salt, and possesses excellent antibacterial, antilipemic and hypoglycemic medicinal value.

Description

technical field [0001] The present invention relates to a novel compound, in particular to a derivative of berberine hydrochloride. Background technique [0002] Berberine, also known as berberine, is a traditional natural antibacterial active substance extracted from Coptis chinensis, and it is mainly used clinically for the treatment of intestinal bacterial infections. Pharmacological studies in recent years have found that berberine hydrochloride and some structural derivatives have various pharmacological activities such as antibacterial, anti-inflammatory, anti-tumor, hypoglycemic and hypolipidemic. Therefore, in-depth research on the pharmacological effects of berberine hydrochloride and structural retrofit work have aroused widespread interest. The research results of Iwasa et al. showed that the antibacterial and other biological activities of berberine derivatives can be increased after adding lipophilic groups to berberine molecules. However, so far, there have b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03A61K31/4375A61P31/04A61P3/10A61P3/06
Inventor 叶小利李学刚
Owner SOUTHWEST UNIV
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