Rosmarinic acid derivative, preparation method and application

A technology of rosmarinic acid and derivatives, which is applied in the field of medicine, can solve the problems of ionizing radiation damage, short-lived, and disappear after a few minutes, and achieve the effect of simple preparation method and easy-to-obtain product

Inactive Publication Date: 2016-06-22
INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional view is that ionizing radiation is caused by rays ionizing water in cells and generating free radicals, which damage biological macromolecules and cause ionizing radiation damage. However, the lifespan of free radicals produced by ionized water is extremely short and will disappear after a few minutes. Injuries cause free radicals in the body to show an increasing trend within a certain period of time, and reach a peak at 24 hours

Method used

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  • Rosmarinic acid derivative, preparation method and application
  • Rosmarinic acid derivative, preparation method and application
  • Rosmarinic acid derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A kind of preparation method of rosmarinic acid derivative (I), comprises the steps:

[0031] (1) Mix 2.8g (0.02mol) 3-bromopropanol (Ⅳ-1) and 5.3g (0.02mol) triphenylphosphine (Ⅲ) into 15ml N,N-dimethylformamide (DMF) at 100°C Reflux the reaction overnight. After the reaction is completed, a large amount of white solids will precipitate out of the cooling reaction system. Filter under reduced pressure, then wash the white solids with cold DMF, and dry them at 50°C overnight to obtain white powdery solid (3-hydroxypropyl) triphenyl Phosphorus bromide (Ⅴ-1);

[0032] (2) Mix 0.36g (0.001mol) rosmarinic acid (Ⅵ) and 0.4g (0.001mol) (3-hydroxypropyl) triphenylphosphine bromide (Ⅴ-1) into 20ml DMF, then add 0.23 g (0.0012mol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 0.14g (0.0012mol) 1-hydroxybenzotriazole (HOBT) and stir well , react overnight at room temperature under nitrogen protection, add saturated NaHCO after fully reacting 3 Aqueous solu...

Embodiment 2

[0037] A kind of preparation method of rosmarinic acid derivative (II), comprises the steps:

[0038] (1)-(2) is the same as (1)-(2) of embodiment 1;

[0039] (3) 0.74g (0.001mol) rosmarinic acid derivative shown in formula (I) is added to 10ml in the aqueous solution of 0.16g (0.004mol) NaOH, after fully dissolving, solvent removal under reduced pressure obtains pale yellow solid, Dry in vacuum at 40°C overnight. A rosmarinic acid derivative represented by formula (II) is obtained.

[0040] The reaction formula is as follows:

[0041]

[0042] R in this example 1 , R 2 , R 3 , R 4 Both are sodium.

[0043] Replace the NaOH of the present embodiment with the KOH of 0.004mol, other is the same as the present embodiment, prepares the rosmarinic acid derivative shown in (II), its R 1 , R 2 , R 3 , R 4 Both are potassium.

experiment example 1

[0045] Determination of cell viability by neutral red method

[0046] 1. Cell culture

[0047] CHO-K1 cells (purchased from the National Experimental Cell Sharing Resource Platform) were stored at a volume concentration of 5% CO 2 cultured in a 37°C incubator, and cultured in RPMI1640 culture medium containing double antibody and 10% fetal bovine serum to the logarithmic phase.

[0048] 2. Determination of cell viability

[0049] CHO-K1 cells cultured to the logarithmic phase were placed in 96-well plates at 4000 cells per well, cultured overnight, and given rosmarinic acid derivatives shown in formula (I) and formula (II) 30 minutes before irradiation. The indicated rosmarinic acid derivative solution (1 μmol / L, the solvent is RPMI1640 medium containing serum and double antibody) was 100 μL per well, cultured in an incubator for 30 min, irradiated with 3 Gy gamma rays, and then continued in the incubator. After culturing for 24 hours, remove the culture solution, then add ...

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Abstract

The invention discloses a rosmarinic acid derivative, a preparation method and application. The rosmarinic acid derivative has the structure (please see the formula in the description) shown in the formula (I) or the formula (II). Experiments prove that the rosmarinic acid derivative can effectively remove reactive oxygen (ROS) generated by ionizing radiation, and therefore the rosmarinic acid derivative has purposes in the aspect of treatment of related diseases, such as the Alzheimer's disease and ionization injury diseases, caused by free radicals. The preparation method is simple, the product is easy to obtain, and pollution is avoided.

Description

technical field [0001] The invention relates to a rosmarinic acid derivative, a preparation method and application thereof, and belongs to the field of medicine. Background technique [0002] In recent years, due to the rapid development of radiation therapy and nuclear medicine, more and more ionizing radiation has entered people's lives. It is inevitable that many people will be accidentally exposed to ionizing radiation, which will cause certain harm to the body. Hazards are divided into direct damage and indirect damage. Indirect damage is a major damage. The principle is that a large number of free radicals produced by ionizing radiation damage the macromolecular proteins, lipids and nucleic acids in the human body. These macromolecular biological function obstacles Or the absence can lead to bodily dysfunction or disease. The traditional view is that ionizing radiation is caused by rays ionizing water in cells and generating free radicals, which damage biological macr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54A61P25/16A61P25/28A61P39/06
CPCC07F9/5442
Inventor 徐文清张宇睿王骏滢王华伟康肖梦王华南
Owner INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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