O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with anti-tumor activity and preparation and application methods thereof

A technology of fluorobenzoyl and anti-tumor activity, which is applied in the field of medicine, can solve the problems of no tumor inhibitory effect and cross-drug resistance, and achieve the effect of simple preparation method and simple purification method

Active Publication Date: 2019-03-08
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of cisplatin also has certain shortcomings. It has no inhibitory effect on certain tumors and is prone to cross-resistance with other platinum agents.
In addition, cisplatin has a variety of side effects, such as nephrotoxicity, peripheral neurotoxicity, bone marrow toxicity, hematological toxicity and emetogenicity, etc.

Method used

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  • O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with anti-tumor activity and preparation and application methods thereof
  • O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with anti-tumor activity and preparation and application methods thereof
  • O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with anti-tumor activity and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] O-(4-bromo-2-fluorobenzoyl) licorice A with anti-tumor activity, its chemical structural formula is as follows:

[0026]

[0027] The preparation method of O-(4-bromo-2-fluorobenzoyl) licorice A with antitumor activity comprises the following steps:

[0028] Add 5 times the mass of acetonitrile to 190 mg of licorice A (0.5 mmoL) to dissolve, add pyridine and 2-fluoro-4-bromobenzoyl chloride, control the reaction temperature between 60-80 ° C and heat under reflux for 35 minutes to obtain The reaction product, the reaction product is evaporated to remove the solvent under reduced pressure to obtain a residue, and the residue is recrystallized to obtain O-(4-bromo-2-fluorobenzoyl) licorice A, wherein, licorice A, pyridine, 2-fluoro The molar ratio of -4-bromobenzoyl chloride is 1:0.1:2, and the solvent used for recrystallization of the residue is absolute ethanol.

[0029] O-(4-bromo-2-fluorobenzoyl)glycyrrhizae A is a white powdery solid with a yield of 61.03%.

[0...

Embodiment 2

[0032] O-(4-bromo-2-fluorobenzoyl) licorice A with anti-tumor activity, its chemical structural formula is as follows:

[0033]

[0034] The preparation method of O-(4-bromo-2-fluorobenzoyl) licorice A with antitumor activity comprises the following steps:

[0035] Add 10 times the mass of acetonitrile to Glycyrrhizae A to dissolve, add pyridine and 2-fluoro-4-bromobenzoyl chloride, control the reaction temperature between 60-80°C and heat under reflux for 30 minutes to obtain the reaction product, the reaction product The solvent was distilled off under reduced pressure to obtain a residue, and the residue was recrystallized to obtain O-(4-bromo-2-fluorobenzoyl)glycyrrhizae A, wherein, licorice A, pyridine, 2-fluoro-4-bromobenzene The molar ratio of formyl chloride was 1:0.1:6, and the solvent used for recrystallization of the residue was acetonitrile.

[0036] O-(4-bromo-2-fluorobenzoyl)glycyrrhizae A is a white powdery solid with a yield of 63.43%.

Embodiment 3

[0038] O-(4-bromo-2-fluorobenzoyl) licorice A with anti-tumor activity, its chemical structural formula is as follows:

[0039]

[0040] The preparation method of O-(4-bromo-2-fluorobenzoyl) licorice A with antitumor activity comprises the following steps:

[0041] Add 15 times the mass of acetonitrile to Glycyrrhizae A to dissolve, add pyridine and 2-fluoro-4-bromobenzoyl chloride, control the reaction temperature between 60-80°C and heat under reflux for 35 minutes to obtain the reaction product, the reaction product The solvent was distilled off under reduced pressure to obtain a residue, and the residue was recrystallized to obtain O-(4-bromo-2-fluorobenzoyl)glycyrrhizae A, wherein Glycyrrhizae A, pyridine, 2-fluoro-4-bromobenzene The molar ratio of formyl chloride was 1:0.1:10, and the solvent used for recrystallization of the residue was ethyl acetate.

[0042] O-(4-bromo-2-fluorobenzoyl)glycyrrhizae A is a white powdery solid with a yield of 66.08%.

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PUM

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Abstract

The invention discloses an O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with anti-tumor activity. The chemical formula of the O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with the anti-tumor activity is shown as the follows. The invention also discloses a preparation method of the O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with the anti-tumor activity and application of the O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with the anti-tumor activity to preparing drugs for treating leukemia, lung cancer and liver cancer. The O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarin robustic acid with the anti-tumor activity is simple in preparation method, and in vitro anti-tumor experiments show that the O-(4-bromo-2-fluorobenzoyl) 3-phenylcoumarinrobustic acid is high in anti-tumor activity.

Description

technical field [0001] The invention relates to the technical field of medicine. More specifically, the present invention relates to O-(4-bromo-2-fluorobenzoyl)glycyrrhizae A with antitumor activity, its preparation method and application. Background technique [0002] Malignant tumor (cancer) is one of the diseases that seriously endanger human health in today's society. Statistics in recent years show that there are about 12 million new cancer patients worldwide, 7.6 million deaths due to cancer, and about 20,000 people die of cancer every day. In addition, the incidence of cancer continues to rise, and it is estimated that there will be 15 million new cancer patients worldwide in 2020. At present, cisplatin has become one of the three most widely used drugs for cancer treatment in the world, with annual sales in the United States reaching nearly 500 million US dollars. However, the use of cisplatin also has certain shortcomings. It has no inhibitory effect on certain t...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D493/04
Inventor 霍丽妮陈睿韦建华卢汝梅李典鹏韦燕飞李培源钟海艺
Owner GUANGXI UNIV OF CHINESE MEDICINE
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