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Polysubstitution resveratrol spin-labeling derivative and preparing method and application thereof

A technology of resveratrol and spin labeling, which can be used in drug combinations, pharmaceutical formulations, active ingredients of hydroxyl compounds, etc., can solve the problems of limited routes of administration, narrow time windows, limitations, etc., and achieve low cytotoxicity and repeatability. Good, the effect of reducing the level of reactive oxygen species

Inactive Publication Date: 2019-08-23
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the shortcomings of amifostine and the limited route of administration and narrow time window, its clinical use is limited.

Method used

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  • Polysubstitution resveratrol spin-labeling derivative and preparing method and application thereof
  • Polysubstitution resveratrol spin-labeling derivative and preparing method and application thereof
  • Polysubstitution resveratrol spin-labeling derivative and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1 Synthesis of Disubstituted Resveratrol Nitroxide Free Radical Derivatives

[0075] Weigh 88 mg (0.38 mmol) of resveratrol, 138.2 mg (1 mmol) of anhydrous potassium carbonate and 8.3 mg of potassium iodide in a 100 mL three-necked round-bottomed flask filled with 10 mL of DMF, and slowly heat to 60 °C under nitrogen protection. Stir for 30 min, then weigh 88.8 mg (0.25 mmol ) into the reaction system, keep the temperature constant, and stir for 10 h.

[0076]At the end of the reaction, add 80 mL of distilled water to the reaction solution, then pour the resulting solution into a separatory funnel, measure 100 mL of ethyl acetate, first take a small amount of washing reaction bottle, and add the remaining ethyl acetate to the funnel for extraction. Stand still, separate the organic layer, dry the organic phase with anhydrous sodium sulfate, filter, and finally remove the solvent under reduced pressure, and purify by column chromatography (ethanol:dichloromethan...

Embodiment 2

[0092] Example 2 Synthesis of Disubstituted Resveratrol Nitroxide Free Radical Derivatives

[0093] Weigh 132 mg (0.57 mmol) of resveratrol, 207.3 mg (1.5 mmol) of anhydrous potassium carbonate and 11 mg of potassium iodide in a 100 mL three-necked round-bottomed flask filled with 15 mL of DMF, and slowly heat to 70 °C under nitrogen protection. After stirring for 30 min, add 4,4,5,5-tetramethyl-2-[4-(2-bromoethoxy)phenyl]-1,3-dioxypyrroline 133.2 mg ), TLC followed the reaction, and the reaction was completed after 15 h. Add 150 mL of distilled water to the reaction solution, pour the obtained solution into a separatory funnel, extract with ethyl acetate (80 mL×3), and use a large amount of saturated salt for the organic phase. Wash with water, finally collect the organic phase, dry over anhydrous sodium sulfate, filter, remove the solvent under reduced pressure, and purify by column chromatography (ethanol:dichloromethane=1:30~60, v / v) to obtain 60 mg of dark blue solid, chr...

Embodiment 3

[0095] Example 3 Synthesis of Disubstituted Resveratrol Nitroxide Free Radical Derivatives

[0096] Weigh 264 mg (1.14 mmol) of resveratrol, 414.6 mg (3 mmol) of anhydrous potassium carbonate and 25 mg of potassium iodide in a 100 mL three-necked round-bottomed flask filled with 15 mL of DMF, and slowly heat to 50 °C under nitrogen protection. After stirring for 30 min, 266.4 mg of 4,4,5,5-tetramethyl-2-[4-(2-bromoethoxy)phenyl]-1,3-dioxypyrroline (0. 75mmol), thin-layer chromatography followed the reaction, and the reaction was completed after 24 h. Add 150 mL of distilled water to the reaction solution, pour the obtained solution into a separatory funnel, extract with ethyl acetate (80 mL×3), and use a large amount of saturated Wash with salt water, finally collect the organic phase, dry over anhydrous sodium sulfate, filter, remove the solvent under reduced pressure, and purify by column chromatography (ethanol:dichloromethane=1:30~60, v / v) to obtain the product as a dark b...

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Abstract

The invention relates to a polysubstitution resveratrol spin-labeling derivative. The polysubstitution resveratrol spin-labeling derivative is a compound shown in a chemical general formula (the formula is defined in the description); in the formula, one derivative or another derivative is defined in the description. The invention also discloses a preparing method and application of the polysubstitution resveratrol spin-labeling derivative. The polysubstitution resveratrol spin-labeling derivative has the advantages of good selectivity and small toxic and side effects, and can serve as an easily-monitored targeted drug for researching an anti-radiation mechanism and in-vivo distribution of the polysubstitution resveratrol spin-labeling derivative.

Description

technical field [0001] The invention relates to a polyphenolic compound, in particular to a multi-substituted resveratrol spin-labeled derivative and a preparation method and application thereof. Background technique [0002] Resveratrol is a polyphenol compound present in plants such as grapes, peanuts, and knotweed. It is a chemopreventive agent for tumors and a natural chemical for reducing platelet aggregation, preventing and treating atherosclerosis, and cardiovascular and cerebrovascular diseases. Preventive agents, which have almost no toxic side effects on humans and animals [C H Cottart, V Nivet-Antoine, C Laguillier-Morizot, et al. Resveratrol bioavailability and toxicity in humans[J]. Molecular nutrition & food research, 2010, 54(1 ): 7-16.]. There are two aromatic rings and three phenolic hydroxyl groups in the resveratrol molecule. Compared with vitamins C and E, it has a higher scavenging 2,2'-azino-bis-(3-ethylbenzodihydro Thiazoline-6-sulfonic acid) (ABTS),...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/54A61K31/05A61K49/10A61P39/00A61P39/06C07D233/22
CPCA61K31/05A61K49/10A61K47/545A61P39/00A61P39/06C07D233/22
Inventor 罗国英唐玮赵亮吴言为董树清李辉
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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