Flavone alkoxy phosphoramidate derivative for targeted Hsp60, preparation and application

A technology for flavonoid alkoxy phosphoramidate and derivatives, which is applied in the field of pharmaceutical compounds, can solve problems such as poor solubility, difficult absorption and metabolism, and achieves the effects of low cost, good antitumor activity, good practical value and application prospect

Active Publication Date: 2018-12-14
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The rich physiological activities of flavonoids have aroused great research interest, but at the same time, these compounds also have problems such as poor solubility and difficulty in being absorbed and metabolized by the body due to self-aggregation.

Method used

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  • Flavone alkoxy phosphoramidate derivative for targeted Hsp60, preparation and application
  • Flavone alkoxy phosphoramidate derivative for targeted Hsp60, preparation and application
  • Flavone alkoxy phosphoramidate derivative for targeted Hsp60, preparation and application

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Embodiment 1

[0029] The preparation of embodiment 1 chrysin-7-ethoxyglycine phosphoramidate

Embodiment 1-1

[0030] Example 1-1: Phenyl dichlorophosphate (1.5mL, 10mmol, 0.4M) was added to a 250mL three-necked flask, then dichloromethane (100mL) was added to dissolve it, and the reaction system was cooled to At -83.5°C, TEA (3 mL, 10 mmol, 1 equiv) was added dropwise to the reaction solution using a constant pressure dropping funnel for 10 min. Then, a mixed solution of 2-bromoethanol (1.1 mL, 8 mmol, 0.8 equiv) and dichloromethane (5 mL) was added dropwise to the above reaction solution, and the dropwise reaction was completed at low temperature for 1 h. Naturally rise to room temperature to react. The progress of the reaction was detected by TLC, and the developer was chloroform:methanol=30:1. The reaction time is about 12h. Add anhydrous dichloromethane (50mL), weigh glycine methyl ester hydrochloride (1.26g, 10mmol, 1equiv) and add to the above reaction system, add TEA (1.5mL) dropwise to the reaction solution with a constant pressure dropping funnel , 20mmol, 2equiv), added d...

Embodiment 1-2

[0031] Example 1-2: Add chrysin (0.254g, 1mmol, 0.01M) in a 250mL three-necked flask, then add acetone (100mL) to dissolve it, add cesium carbonate (0.488g, 1.5mmol, 1.5equiv), and then add Ethoxyglycine phosphoramidate (1.840g, 5mmol, 5equiv), the reaction was placed in an oil bath at 50°C for reaction, and the reaction progress was detected by TLC. The developing agent was petroleum ether: ethyl acetate=3:2, and the reaction time was 6~ 7d, after the reaction is over, stop stirring. Post-treatment: filter to remove insoluble matter, evaporate the solvent under reduced pressure to obtain a yellow oily liquid, which is separated by column chromatography. The column chromatography conditions are petroleum ether:ethyl acetate=3:2, and after concentration, a light yellow solid is obtained. The yield is 10%. The results of instrumental analysis of the compound structure: 1 H NMR (400MHz, DMSO-d6 ), δ: 12.82(s, 1H, 5-OH), 8.10(d, 2H, J=6.8Hz, H-2′, H-6′), 7.64(m, 1H, H-4′), 7.60 ...

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PUM

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Abstract

The invention discloses a flavone alkoxy phosphoramidate derivative for targeted Hsp60, a preparation and application. The flavone alkoxy phosphoramidate derivative for the targeted Hsp60 has the advantages of simple and easy preparation method and low cost. A series of novel flavone alkoxy phosphoramidate derivative with anti-tumor activity is designed and synthesized to realize an obvious inhibition and killing effect on breast cancer cells and hepatoma carcinoma cells and realize no obvious inhibition effect on normal hepatocyte. The flavone alkoxy phosphoramidate derivative for the targeted Hsp60, disclosed by the invention, has the advantages that the selective flavone alkoxy phosphoramidate derivative for the targeted Hsp60 is developed, and the flavone alkoxy phosphoramidate derivative for the targeted Hsp60 has very good practical values and application prospects in the field of preparing anti-tumor drugs.

Description

technical field [0001] The invention relates to a class of pharmaceutical compounds, in particular to a class of flavone alkoxy phosphoramidate derivatives targeting Hsp60, its preparation and application. Background technique [0002] Flavonoids belong to a very important class of polyphenolic compounds. Flavonoids are abundant in fruits and vegetables and have various physiological activities. Flavonoids have great therapeutic value and potential for hypertension and other cardiovascular diseases, inflammation, diabetes, immune system diseases and other diseases that endanger human health. In addition, the compounds have good effects in preventing different types of cancers such as liver cancer, prostate cancer, colon cancer and lymphoblastic leukemia. Among them, chrysin can inhibit tumor cell growth and proliferation by inducing apoptosis and reducing inflammation. Soy isoflavones, known as "phytoestrogens", are also antioxidants that can protect cells from damage caus...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655A61P35/00
CPCA61P35/00C07F9/65522
Inventor 李悦青赵伟杰李广哲吴茜茜董伊王柳郭修晗
Owner DALIAN UNIV OF TECH
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