Leonurine borneol derivative as well as preparation method and application thereof

A technology of motherwort and derivatives, applied in the field of medicine, can solve problems such as unbeneficial motherwort borneol derivatives, etc., and achieve the effects of repairing nerve cell damage and improving survival rate.

Active Publication Date: 2021-11-05
WEIFANG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the prior art, there are no reports

Method used

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  • Leonurine borneol derivative as well as preparation method and application thereof
  • Leonurine borneol derivative as well as preparation method and application thereof
  • Leonurine borneol derivative as well as 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 invention provides a leonurine borneol derivative, the leonurine borneol derivative is a compound shown as B1 or B2 or a stereoisomer or a pharmaceutically acceptable salt form thereof, and the invention also provides a preparation method of the derivative and an application of the derivative in a medicine for preventing and treating nervous system diseases or cardiovascular and cerebrovascular diseases. The leonurine borneol derivative provided by the invention has a remarkable neuroprotective effect, can repair nerve cell injury, and also can play a role in obviously reducing lipid, so that the leonurine borneol derivative has remarkable pharmacological activity for treating and preventing nervous system and cardiovascular and cerebrovascular diseases, has important significance for developing novel drugs for preventing or treating 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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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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