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Preparation method and application of novel ferrocene derivative containing free radicals of nitroxide

A technology of ferrocene derivatives and nitroxide free radicals, applied in the field of medicine, can solve the problems of poor overall clinical treatment effect and difficult cancer treatment.

Active Publication Date: 2015-07-29
厦门奥德生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, most cancers are found in the middle to late stages, and the overall effect of clinical treatment is poor, especially the continuous emergence of multidrug resistance, which makes cancer treatment difficult.

Method used

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  • Preparation method and application of novel ferrocene derivative containing free radicals of nitroxide
  • Preparation method and application of novel ferrocene derivative containing free radicals of nitroxide
  • Preparation method and application of novel ferrocene derivative containing free radicals of nitroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1 Synthesis of ferrocene derivatives I containing nitrogen and oxygen free radicals

[0048] Add cyanuric chloride (TCT) (0.184g, 1 mmol) and 30 mL of dry tetrahydrofuran into a 100 mL round-bottomed flask, stir in an ice bath, and dry 20 mL of ferrocenemethanol (0.864 g, 4 mmol) THF solution was slowly added dropwise to the reaction system. After stirring in an ice bath for 30 minutes, slowly add 10 mL of dry tetrahydrofuran solution containing DMAP (0.366 g, 3 mmol) into the reaction system dropwise, stir in an ice bath for 30 minutes, then naturally rise to room temperature for reaction, and react at room temperature for 5-6 hours , followed by reflux reaction, after the completion of the TLC detection reaction, the reaction solution was concentrated under reduced pressure, and the residue was directly separated by column, and used ( V 石油醚 : V 乙酸乙酯 , 5:1-2:1) mobile phase elution to obtain ferrocene derivative I containing nitroxide free radicals, 0.5...

Embodiment 2

[0050] Example 2 Single crystal cultivation and XRD characterization

[0051] Take a small amount of ferrocene derivatives containing nitrogen and oxygen free radicals obtained in Example 1, dissolve them in a mixed solution of ethyl acetate / petroleum ether (V / V, 1:4), and naturally volatilize and crystallize at room temperature to obtain light yellow Needle crystals. The obtained crystals were characterized by XRD, the space group is P-1, and the unit cell parameters are a =13.8909?, b=15.1596?, c=16.1133?; α= 74.027 o , β=77.179 o , γ=80.454 o ; V=3160.88 ? 3 , Z=4, R1=0.0437.

Embodiment 3

[0052] Example 3 Anticancer Activity Experiment

[0053] MTT method was used to screen the activity of human lung cancer cell line (A549) and breast cancer cell line MCF-7.

[0054] The specific experimental operation process is as follows:

[0055] (1) The colorectal cancer cell line A549 in the logarithmic growth phase was inoculated in a 96-well culture plate and cultured. When the cells grew to 90%, 1 μL of 1×10 -4 The test sample of M was added, and its concentration was set to 3 duplicate wells, and a positive control (gefitinib) was set, and a negative control was 1 μL (DMSO+cell culture solution+MTT). Then at 37℃, 5%CO 2 Cultivate under conditions for 48 hours; (2) Then add 20 μL of 5mg / mL MTT solution to each well, shake gently and continue for several minutes, then continue to cultivate for 3-4 hours, then suck out the culture solution; (3) Each well Add 100 μL of DMSO and shake on a shaker at low speed for 10 minutes to fully dissolve the crystals. Meas...

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Abstract

The invention discloses a preparation method and application of a novel ferrocene derivative containing free radicals of nitroxide. The ferrocene derivative containing free radicals of nitroxide, pharmaceutically acceptable salt or a pharmaceutically acceptable solvate of the ferrocene derivative, or a pharmaceutical composition is shown in formula (I). The novel ferrocene derivative shown in the formula (I) has very high inhibitory activity on a lung cancer cell line A549 and a breast cancer cell line MCF-7, and can be used as a candidate compound or a lead compound for treatment of cancer, tumor and other diseases.

Description

technical field [0001] The invention belongs to the field of medicine, relates to a ferrocene derivative containing a nitrogen-oxygen free radical with a novel structure, and specifically relates to the preparation of the ferrocene derivative, a pharmaceutical composition containing the compound and its application. [0002] The compound has strong inhibitory activity on the proliferation of human lung cancer cell line A549 and breast cancer cell line MCF-7. The compound has broad-spectrum anticancer activity and can be used as a candidate drug or a lead compound for treating diseases such as tumors and cancers. Background technique [0003] Cancer has become the most important fatal disease in the world, and the mortality rate of cancer patients in developed countries is also high. Cancer can occur in various organs and tissues at any age. The main types of cancer that cause death are: lung cancer, stomach cancer, liver cancer, colon cancer and breast cancer. In recent ye...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61K31/555A61P35/00
CPCA61K31/555C07F17/02
Inventor 雍建平卢灿忠
Owner 厦门奥德生物科技有限公司
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