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A kind of motherwortine borneol derivative, preparation method and application thereof

A technology of Leonurine and its derivatives, which is applied in the field of medicine, can solve the problems of unsatisfactory Leonurine borneol derivatives, etc., and achieve the effect of repairing nerve cell damage and improving survival rate

Active Publication Date: 2022-02-11
WEIFANG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, there are no reports of beneficial motherwort borneol derivatives

Method used

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  • A kind of motherwortine borneol derivative, preparation method and application thereof
  • A kind of motherwortine borneol derivative, preparation method and application thereof
  • A kind of motherwortine borneol derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: The synthetic route of M-1 is as follows:

[0057]Add camphene (15.0g, 0.1mol), 2-bromoethanol (13.6g, 0.11mol) and montmorillonite K-10 (30.0g) into dichloromethane (200mL), stir at room temperature for 24 hours, and the reaction is complete After filtering, the filter cake was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and column chromatography gave colorless oil M1 with a yield of 72%; ESI-MS: (m / z, %)= 260[M+H] + .

Embodiment 2

[0058] Embodiment 2: The synthetic route of M-2 is as follows:

[0059] Dissolve syringic acid (5.94g, 30mmol) in 30mL of dichloromethane to obtain a dichloromethane solution of syringic acid, add potassium hydroxide (3.0g, 54mmol), potassium carbonate (4.1g, 30mmol), tetrabutyl ammonium bromide (1.0g, 3 mmol) and water 30mL, slowly add M-1 (7.8g, 30mmol) in dichloromethane (10mL) solution dropwise under stirring, dropwise in 30 minutes, react at room temperature for 24 hours, After the reaction was complete, the pH was adjusted to 5, the organic layer was separated, and the organic phase was washed with water in an amount of 30 mL. After washing with water, it was concentrated to dryness. M-2 was obtained by column chromatography with a yield of 51%. 1 H NMR (500 MHz, DMSO- d 6 ) δ = 7.28 (s, 2H), 4.13(t, 2H), 3.81 (s, 6H), 3.76 (t, 2H), 3.04 (m, 1H), 1.86-1.55 (m, 7H), 1.01(s , 3H), 0.97 (s, 6H). ESI-MS: (m / z, %) = 379 [M+H] + .

Embodiment 3

[0060] Embodiment 3: The synthetic route of M-4 is as follows:

[0061] M-2 (6.3 g, 16.66 mmol) was dissolved in 100 mL of DCM at room temperature, M-3 (6 g, 24.98 mmol), 4-dimethylaminopyridine p-toluenesulfonate (9.8 g, 33.32 mmol), N, N'-diisopropylcarbodiimide (4.2 g, 33.32 mmol), reacted for 5 h, washed with water, extracted with DCM, collected the lower layer solution, evaporated to dryness, and obtained white foamy solid by column chromatography M-4, yield 67%.

[0062] 1 H NMR (500 MHz, DMSO- d 6 ) δ = 9.31 (s, 1H), 8.33 (s, 1H), 7.20 (s,2H), 4.24-4.20 (m, 1H), 4.13 (t, 2H), 4.02 (q, 1H), 3.80 (s , 6H), 3.75 (t,2H), 3.04 (m, 1H), 1.98-1.56 (m, 13H), 1.46 (s, 9H), 1.37 (s, 9H), 1.01 (s,3H), 0.97 ( s, 6H). ESI-MS: (m / z, %) = 692 [M+H] + .

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Abstract

The present invention provides a derivative of Leonurine Borneolum, which is a compound represented by B1 or B2 or its stereoisomer or a pharmaceutically acceptable salt form thereof. The present invention also provides a derivative of the above derivative The preparation method and its application in medicines for preventing and treating nervous system diseases or cardiovascular and cerebrovascular diseases. The motherwortine borneol derivatives provided by the present invention have significant neuroprotective effects, can repair nerve cell damage, and can also significantly reduce lipids, so they have significant pharmacological activities for treating and preventing nervous system, cardiovascular and cerebrovascular diseases, It is of great significance for the development of new drugs for the prevention or treatment of nervous system and cardiovascular and cerebrovascular diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a leonurine borneol derivative, a preparation method thereof and an application in medicines for preventing and treating nervous system diseases or cardiovascular and cerebrovascular diseases. Background technique [0002] Stroke is a major disease that seriously endangers human health and life safety in the world today. It has the characteristics of high morbidity, disability and mortality. A group of disorders that cause damage to brain tissue, including ischemic and hemorrhagic stroke. The incidence of ischemic stroke is higher than that of hemorrhagic stroke, accounting for 60% to 70% of the total number of strokes. There are more than 10 million new strokes every year in the world. The survey shows that stroke has become the number one cause of death in my country and the number one cause of disability in Chinese adults. It has brought serious burdens to societ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/06C07C43/225C07C51/367C07C65/26C07C277/08C07C279/08C07C279/24A61K31/235A61P25/00A61P9/00A61P9/10A61P25/28A61P25/16A61P25/20A61P25/08A61P25/18A61P3/10A61P9/12A61P3/06
CPCC07C41/06C07C43/225C07C51/367C07C65/26C07C277/08C07C279/08C07C279/24A61P25/00A61P9/00A61P9/10A61P25/28A61P25/16A61P25/20A61P25/08A61P25/18A61P3/10A61P9/12A61P3/06C07C2602/42
Inventor 李峰宋艳宋晓峰李文保刘晓坤张姗姗
Owner WEIFANG UNIV OF SCI & TECH
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