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Pterostilbene compound myocardium targeted preparation and application thereof

A technology of pterostilbene and its compounds, which is applied in the field of medicine, can solve the problems that the drug tissue specificity is difficult to reach the lesion site, easy to degrade and unstable, etc., and achieve the effects of reducing drug dosage, simple and easy preparation method, and reducing drug concentration

Inactive Publication Date: 2018-07-24
董少红
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, there are many drugs currently used for cardiovascular treatment, but due to the physiological characteristics of cardiovascular diseases, most drugs lack tissue specificity and are difficult to reach the lesion site, and there are also problems of easy degradation and instability in the body

Method used

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  • Pterostilbene compound myocardium targeted preparation and application thereof
  • Pterostilbene compound myocardium targeted preparation and application thereof
  • Pterostilbene compound myocardium targeted preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthesis Example 1: (E)-2-(4-(4-(3,5-dimethoxystyryl)phenoxy)phenyl)-5,7-dimethoxy-4H-benzene Synthesis of pyran-4-one (PTE-FLA-1)

[0059]

[0060] Dissolve pterostilbene (5mmol) and potassium carbonate (10mmol) in 50ml of ethanol at 50°C, then add 2-(4-chlorophenyl)-5,7-dimethoxy-4H-benzopyran -4-ketone (5mmol), the system was heated to reflux, and stirred for 7 hours under reflux. After the reaction was monitored by TLC, it was cooled to room temperature, insolubles were removed by filtration, ethanol was removed by rotary evaporation, and the residue was separated by silica gel column chromatography, using ethyl acetate / petroleum ether=1:5 as eluent, and the target product The liquid was evaporated to remove the solvent, and heated and dried under vacuum to obtain 2.2 g of the target compound as a white solid, with a yield of 83.4%.

[0061] Elemental analysis: theoretical value / measured value, C(73.87 / 74.03), H(5.26 / 5.11), O(20.87 / 20.86)

[0062] ESI-MS: 537...

Embodiment 2

[0064] Synthesis Example 2: (E)-2-(4-(4-(3,5-dimethoxystyryl)phenoxy)phenyl)-5,7-dimethoxy-benzopyridine Synthesis of Pyran-4-one (PTE-FLA-2)

[0065]

[0066] Dissolve pterostilbene (5mmol) and potassium carbonate (10mmol) in 50ml of ethanol at 50°C, then add 2-(4-chlorophenyl)-5,7-dimethoxy-benzopyran-4 - Ketone (5mmol), the system was heated to reflux, and stirred for 8 hours under reflux. After the reaction was monitored by TLC, it was cooled to room temperature, the insoluble matter was removed by filtration, ethanol was removed by rotary evaporation, and the residue was separated by silica gel column chromatography, using ethyl acetate / cyclohexane=1:5 as eluent, and collected The liquid product was evaporated to remove the solvent, and dried under vacuum to obtain 2.1 g of the target compound as a white solid with a yield of 79.5%.

[0067] Elemental analysis: theoretical value / measured value, C(73.59 / 73.39), H(5.61 / 5.73), O(20.79 / 20.88)

[0068] ESI-MS: 539[M+H] ...

Embodiment 3

[0070] Synthesis Example 3: Synthesis of Histidine-modified Vitamin E Polyethylene Glycol Succinate (TPGS-His)

[0071]

[0072] 60g TPGS and 17.5g Boc-His were dissolved in 300ml of pyridine, then 18g EDC·HCl and 12.7g HOBT were added, stirred at room temperature for 10h, and the reaction was monitored by TLC. After the reaction was completed, the solvent was removed by rotary evaporation under reduced pressure, and the residual The product was separated by silica gel column chromatography with MeOH / petroleum ether (1:20) as eluent to obtain TPGS-His-Boc. Dissolve it in ethanol again, pass through dry HCl gas, neutralize and wash with NaOH after the reaction is completed, remove the solvent by rotary evaporation under reduced pressure, the residue is separated by silica gel column chromatography, and MeOH / petroleum ether (1:10) is used as The eluent finally obtained TPGS-His 28.5g.

[0073] Histidine-modified polyethylene glycol 12-hydroxystearate (HS-15-His), tryptophan-...

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Abstract

The invention relates to a myocardium targeted preparation containing a pterostilbene compound. Specifically, the pterostilbene compound includes pterostilbene and analogues thereof. Because of structural modification optimization, pterostilbene analogues have more prominent effect than pterostilbene in the aspect of preventing myocardial ischemia reperfusion injury. After intravenous injection, the myocardium targeted preparation can enable slow release of pterostilbene compound so as to prolong the half-life period in blood plasma, at the same time can concentrate the pterostilbene compoundat the heart part relatively, thereby increasing the concentration in myocardium, improving the effect of the pterostilbene compound on myocardial ischemia reperfusion injury, especially diabetic myocardial ischemia reperfusion injury, also the drug dosage can be reduced, and the drug concentration of other tissue parts in the whole body can be reduced relatively, therefore the toxic and side effects are reduced.

Description

technical field [0001] The present invention relates to the field of medicine, in particular, the present invention relates to a myocardial targeting preparation containing pterostilbene compounds, and the present invention also relates to the preparation method of said preparation and its role in preventing myocardial ischemia-reperfusion injury, especially diabetic myocardium Application in ischemia-reperfusion injury. Background technique [0002] Diabetes is a metabolic disease caused by a variety of factors such as genetics, changes in diet and living habits. Due to the relative or absolute deficiency of insulin secretion in the body, the disorder of sugar, fat and protein metabolism in the body is caused, and its main feature is hyperglycemia. Recent studies have shown that the overall incidence of diabetes in China is about 11.6%, and the incidence of prediabetes is 50.1%. Ischemic heart disease is the main cardiovascular complication and the leading cause of death i...

Claims

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Application Information

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IPC IPC(8): A61K9/107A61K47/18A61K47/22A61K31/352A61P9/10A61P3/10
CPCA61K9/1075A61K31/352A61K47/183A61K47/22
Inventor 董少红刘峰熊玮吴美善刘华东贺俊波
Owner 董少红
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