Long chain alkyl berberine salt derivative, synthetic method and use

A technology of berberine salt and long-chain alkyl group, applied in the field of new compounds and their medical uses, can solve the problems such as no literature report, no report, etc.

Inactive Publication Date: 2008-01-16
重庆神农投资(集团)股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The applicant's previous research results show that after the introduction of long-chain alkyl (ethane to 12 alkyl) at the 8-position, its antibacterial activity increases, and when it reaches the 8-alkyl berberine, the antibacterial activity is the largest, and then declines; about the 9-position The synthesis of long-chain alkoxy groups (carbon chain length 6 or more) and the synthesis of 3-position alkoxy groups, as well as the research on their activity, have not been reported; especially about the reduction of blood fat and blood sugar of berberine alkyl modified derivatives There is no literature report on the

Method used

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  • Long chain alkyl berberine salt derivative, synthetic method and use
  • Long chain alkyl berberine salt derivative, synthetic method and use
  • Long chain alkyl berberine salt derivative, synthetic method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: 8-tetradecylberberine hydrochloride.

[0062]

[0063] It is prepared as follows:

[0064] ①. Dry all reaction glass instruments, weigh 0.1 mol of dried magnesium chips and place in a 250 mL three-neck flask, use 40 mL of anhydrous tetrahydrofuran as the reaction solvent, add 0.1 mol of n-tetradecane chloride under nitrogen protection, and prepare corresponding Grignard reagents.

[0065] 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.

[0066] 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.

[0067] ④, centrifuge the reaction solution, take the supernatant,...

Embodiment 2

[0070] Example 2: 8-octadecyl berberine bromate

[0071]

[0072] Its preparation process is as follows:

[0073] 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 brominated n-octadecane under nitrogen protection, and prepare corresponding Grignard reagents.

[0074] 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.

[0075] 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.

[0076] ④, centrifuge the reaction solution, take the supernatant, then add diethyl ether to ex...

Embodiment 3

[0079] Example 3: 8-hexadecyl-12-bromoberberine bromate

[0080]

[0081] Its preparation process is as follows:

[0082] Dissolve 0.1 mole of 8-hexadecyl berberine bromate in 100 ml of acetic acid, add 0.5 mole of bromine, react at room temperature for 30 minutes, cool to -10°C, filter; dissolve the precipitate in ethanol and recrystallize once , to obtain 8-hexadecyl-12-bromoberberine bromate product.

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Abstract

The present invention relates to a class of chemically named long chain alkyl berberine salt derivatives (hydrochloride or Bromate or iodate or hydrofluoric acid salt), and the molecular structural formula is stated above, wherein, X is equal to F-, Cl-, Br-, I-, SO42-, NO3-, PO43-, citric acid radical, acetic acid radical or lactic acid radical. R1, R2, R3, R4, R5 see table above. The class of the substances is provided with obvious hypoglycemic and hypolipidemic activities which are significantly higher than that of berberine salt, so that the invention is a very promising new compound with hypoglycemic and hypolipidemic medicinal values.

Description

technical field [0001] The present invention relates to a class of novel compounds and their medical application, in particular to a derivative of long-chain alkyl berberine salt. 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, the in-depth research on the pharmacological effects of berberine hydrochloride and the structural modification work have aroused widespread interest. The results of the study on the structure-activity relationship of berberine showed that the introduction of an alkyl group (from methane to octane) at the 8-position...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03A61K31/4375A61P3/06A61P3/10
Inventor 叶小利李学刚
Owner 重庆神农投资(集团)股份有限公司
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