1, 5-diaryl-1, 2, 4-triazole compounds and pharmacy use thereof

A technology of triazoles and compounds, applied in drug combinations, organic chemistry, antineoplastic drugs, etc.

Active Publication Date: 2017-03-29
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the important role of myoferlin protein in the process of tumor metastasis, and there is no chemotherapy drug specifically targeting myoferlin on the market, myoferlin has good target innovation as a potential drug target, and the development of targeting myoferlin Protein anti-tumor drugs have broad market prospects

Method used

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  • 1, 5-diaryl-1, 2, 4-triazole compounds and pharmacy use thereof
  • 1, 5-diaryl-1, 2, 4-triazole compounds and pharmacy use thereof
  • 1, 5-diaryl-1, 2, 4-triazole compounds and pharmacy use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Embodiment one: the preparation of each compound

Embodiment 1-1

[0122] Example 1-1, 3-(5-(4-methoxyphenyl)-3-methyl-1H-1,2,4-triazol-1-yl)-N-(4-phenylbutyl base) benzamide

[0123] Take compound 4-methoxybenzoic acid (304mg, 2.0mmol) and acetamidine hydrochloride (284mg, 3.0mmol) in N,N-dimethylformamide, under argon atmosphere, add in ice bath HATU (826mg, 2.2mmol) and DIEA (1.39mL, 8.0mmol) were stirred for 5min, then changed to room temperature (25°C) and stirred for 4h. After cooling, the compound 3-hydrazinobenzoic acid methyl ester (1329mg, 8.0mmol) was added Warm up to 80°C with glacial acetic acid (1.14mL, 20mmol), react for 3h, then cool to room temperature, wash the reaction solution twice with saturated aqueous sodium bicarbonate until no bubbles are generated, extract with ethyl acetate, wash the ethyl acetate layer with saturated saline After drying with anhydrous sodium sulfate, the organic phase was evaporated to dryness. After purification by column chromatography, the compound 3-(5-(4-methoxyphenyl)-3-methyl-1H-1,2,4-tri...

Embodiment 2

[0133] Example 2: The compound target verification experiment of the present invention

[0134] The cell lysate of breast cancer cell MDA-MB231 was co-incubated with biotin or MF041 coupled with biotin at 4°C for 12h. Then each group was added to the agarose beads of streptavidin and continued to incubate for 2h. The agarose beads were collected by centrifugation, the proteins were eluted with 2× loading buffer, and separated by SDS-polyacrylamide gel electrophoresis. After the polyacrylamide gel was silver-stained, the specific target band was excised and identified by mass spectrometry, and it was found that the compound of the present invention can be effectively combined with myoferlin. Take MF041 as an example: the results of silver staining are as follows: figure 1 As shown, in the target verification binding experiment, it was found that the three proteins only appeared in the biotin-coupled MF041 group, but not in the biotin group, indicating that they are proteins t...

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Abstract

The invention discloses 1, 5-diaryl-1, 2, 4-triazole compounds or pharmaceutically acceptable salts thereof shown as structural formula (I)-(III), and pharmaceutical compositions containing the compounds. The invention also discloses application of the compounds or pharmaceutically acceptable salts thereof in preparation of drugs for treatment of various malignant tumors and tumor metastasis related diseases. The compounds shown as formula (I)-(III) can realize concentration gradient dependent inhibition of the proliferation, invasion, infiltration and the like of breast cancer cells, prostate cancer cells, colon cancer cells, liver cancer cells, non-small cell lung cancer cells, bladder cancer cells and other tumor cells, have low toxicity, and have wide application prospects in bio-pharmaceutical industry.

Description

technical field [0001] The invention relates to a class of 1,5-diaryl-1,2,4-triazole compounds and related analogues, and the compounds or pharmaceutical compositions containing them can be used to prepare and treat various malignant Drugs for tumors and related diseases of tumor metastasis. The invention also relates to a preparation method of the 1,5-diaryl-1,2,4-triazole compound. Background technique [0002] Cancer, also known as malignant tumor, is one of the main causes of disease death worldwide. Nowadays, the morbidity and mortality of many cancers are still showing a trend of rapid growth, seriously endangering human health. According to statistics from the American Cancer Society, the main cause of clinical death of more than 90% of cancer patients is not tumor growth in situ, but distant metastasis of tumor cells. [0003] Tumor metastasis is a complex process: tumor cells are released from the primary tumor site and invade surrounding tissues, enter the blood...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D401/12C07D409/12C07D403/12C07D405/12C07D401/04C07D417/12A61K31/4439A61K31/4196A61K31/427A61P35/00A61P35/04A61P35/02
CPCC07D249/08C07D401/04C07D401/12C07D403/12C07D405/12C07D409/12C07D417/12
Inventor 陈益华易正芳李云齐贺源李静婕刘明耀
Owner EAST CHINA NORMAL UNIV
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