Application of pyrazole hydrazone derivative in preparation of anti-breast cancer drug

An anti-breast cancer, breast cancer technology, applied in drug combinations, anti-tumor drugs, organic chemistry, etc., to achieve the effect of inhibiting growth and good development and application prospects

Inactive Publication Date: 2015-04-29
SHANDONG UNIV QILU HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the introduction of the acylhydrazone chemical structure, pyrazoles form the newly synthesized (E)-N-(4-methoxybenzylidene)-1-(3-(6-chloropyridyl)methyl)- 3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide compound, and research on the application of this compound in the preparation of anti-triple negative breast cancer drugs has not been reported

Method used

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  • Application of pyrazole hydrazone derivative in preparation of anti-breast cancer drug
  • Application of pyrazole hydrazone derivative in preparation of anti-breast cancer drug
  • Application of pyrazole hydrazone derivative in preparation of anti-breast cancer drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (E)-N-(4-methoxybenzylidene)-1-(3-(6-chloropyridine)methyl)-3-(4-chlorophenyl)-1H-pyrazole-5- Preparation of carbohydrazide

[0032]1) Add 0.690 gram of potassium carbonate (0.005 mol), 1.253 gram of 3-(4-chlorophenyl)-1H-pyrazole-5-carboxylic acid ethyl ester (0.005 mol), 0.810 gram of 2 -Chloro-5-chloromethylpyridine (0.005 mol) and acetonitrile (25 ml), equipped with a reflux condenser, the upper part is connected to a drying tube. Heat to reflux for 2 hours, react until the raw material is completely consumed, and detect the end point of the reaction by TLC. Concentrate under reduced pressure, remove the solvent, add ethyl acetate (30 ml), filter, concentrate the filtrate, and use ethyl acetate-petroleum ether (V / V=1 / 2) as the eluent to separate the residue by silica gel column chromatography (100~ 200 mesh silica gel) to obtain ethyl 1-(3-(6-chloropyridine)methyl)-3-(4-chlorophenyl)pyrazole-5-carboxylate with a yield of 90%.

[0033] 2) Add 1.2 mL of 80% Hydraz...

Embodiment 2

[0048] Determination of (E)-N-(4-methoxybenzylidene)-1-(3-(6-chloropyridine)methyl)-3-(4-chlorophenyl)-1H-pyrazole by SRB method -5-carbohydrazide half inhibitory concentration on growth of breast cancer cells

[0049] at 37°C with 5% CO 2 MDA-MB231 breast cancer cells were cultured with DMEM / 10% fetal bovine serum medium under the environment of . MDA-MB-231 breast cancer cells in logarithmic phase were collected, seeded in 96-well plates, and incubated for 24 hours. Add different concentrations (50, 10, 1, 0.5, 0.25, 0.1, 0.05, 0.01 μM) of (E)-N-(4-methoxybenzylidene)-1-(3-(6-chloropyridine ) methyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide was incubated for 48 hours, then 50 μL of trichloroacetic acid solution (30%) was added and fixed at 4° C. for one hour. Shake off the solution, rinse with high-purity water five times, add 100 μL sulforhodamine B to stain for 30 minutes after drying, rinse with 1% acetic acid solution five times after drying. After drying, add...

Embodiment 3

[0052] Determination of (E)-N-(4-methoxybenzylidene)-1-(3-(6-chloropyridyl)methyl)-3-(4-chlorophenyl)- by PI staining flow cytometry Effect of 1H-pyrazole-5-carbohydrazide on the cell cycle of breast cancer

[0053] The MDA-MB-231 breast cancer cells in the logarithmic growth phase were inoculated into 6 cm culture dishes according to the number of 200,000 cells in 3 mL of medium volume, and a total of 16 culture dishes were inoculated. After 24 hours, 16 Petri dishes were equally divided into four groups. Among the four culture dishes in each group, two culture dishes were added with DMSO, and two culture dishes were added with 2.0 μM compound (E)-N-(4-methoxybenzylidene)-1-(3-(6-chloro pyridyl)methyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide. After the four groups were incubated for 2h, 4h, 6h, and 12h, the cells were digested on ice, and the cell suspension was collected, centrifuged, and washed twice with PBS. Add 10 ml of 70% ice ethanol to suspend at -20°C over...

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Abstract

The invention discloses an application of a compound (E)-N-(4-methoxy benzylidene)-1-(3-(6-chloropyridine)methyl)-3-(4-chlorphenyl)-1H-pyrazole-5-carbohydrazide in preparation of an anti-breast cancer drug, wherein the breast cancer is triple-negative breast cancer specifically. Experiments verify that the compound has an obvious effect in inhibition of MDA-MB-231 breast cancer cell proliferation and induction of apoptosis, an anti-tumour test effect is good and no toxic or side effect is produced, so that the compound has a good development application prospect in preparation of the anti-breast cancer drug and can become an effective anti-cancer drug for the triple-negative breast cancer with less optional drugs at present.

Description

technical field [0001] The present invention relates to the application of a pyrazole acylhydrazone derivative in the preparation of anti-breast cancer drugs, in particular to a (E)-N-(4-methoxybenzylidene)-1-(3-(6 Application of -chloropyridine)methyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide in the preparation of anti-breast cancer drugs. Background technique [0002] Breast cancer is the cancer with the highest incidence rate among female malignant tumors, and according to the statistics of the Ministry of Health, its incidence rate is increasing year by year. In medicine, breast cancer cells are divided into four types according to the receptor status of breast cancer cells. Among them, triple-negative breast cancer refers to a special type of breast cancer that is negative for estrogen receptor, progesterone receptor and human epidermal growth factor receptor. It is currently the most difficult type of breast cancer to treat. The main treatment for such patients...

Claims

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Application Information

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IPC IPC(8): A61K31/4439A61P35/00C07D401/06
CPCA61K31/4439C07D401/06
Inventor 邵梅英王博王建峰王娟
Owner SHANDONG UNIV QILU HOSPITAL
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