Acridone derivative containing galactose, preparation method and application thereof

A technology of acridone and galactose, applied in the field of acridone derivatives and its preparation, can solve the problem of no acridone derivatives, etc., achieve good biological activity and anticancer activity, less by-products, and less reaction The effect of mild conditions

Inactive Publication Date: 2019-02-15
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, galactose can modify acridone compounds to a certain extent, however, there is no relevant record of acridone derivatives containing galactose

Method used

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  • Acridone derivative containing galactose, preparation method and application thereof
  • Acridone derivative containing galactose, preparation method and application thereof
  • Acridone derivative containing galactose, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Take the above compound as an example to specifically describe the synthesis process:

[0024] Step S1: Using DMF as a solvent, put a small amount of 9(10H)-acridone (98wt%) (1g about 5.1mmol) into a round bottom flask, place it on a constant temperature magnetic stirrer, and then add (0.41g about 10.2 mmol) sodium hydride, stirred at room temperature for about 1.5 h, then added dropwise (3.1 mL about 30.6 mmol) of 1.3-dibromopropane to the reaction system, placed in an oil bath at 80° C. for about 24 h, and took it out. Wait until the reaction system is down to room temperature, extract with ethyl acetate, after the TLC spot plate monitors the reaction is complete, dry the organic phase, rotary evaporate and mix the sample, and separate through column chromatography to obtain compound 1 acridine bromide (0.95g about 3mmol, yield 59%).

[0025] 1 HNMR (600MHz, CDCl 3 )δ8.52(d, J=7.8Hz, 2H), 7.68(t, J=7.8Hz, 2H), 7.50(d, J=8.4Hz, 2H), 7.24(t, J=7.4Hz, 2H) ...

Embodiment 2

[0042] Some structures of the compounds obtained according to the above synthesis method:

[0043]

Embodiment 3

[0045] Activity data analysis of preliminary determination of some compounds:

[0046] The anticancer activity of the synthesized galactose-containing acridone derivatives was determined by MTT method. Human gastric cancer cells MGC-803 and human breast cancer cells MCF-7 were respectively inoculated in the corresponding medium containing 10 wt% fetal calf serum, at 37 °C, with a volume fraction of 5% CO 2 and saturated humidity conditions, the logarithmic growth phase cells were inoculated into 96-well culture plates, incubated in the incubator for 24 hours, and replaced with different concentrations of compounds (0, 3, 6, 9, 12, 15, 18 μM / L) complete culture medium. After culturing for 72 hours, add 20 μL of MTT (5 mg / mL), continue to cultivate for 4 hours, then slowly absorb the supernatant, add 150 μL of DMSO, shake and shake for 10 minutes to fully dissolve the crystals, and then use a microplate reader to detect the absorbance.

[0047] Preliminary biological activity ...

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PUM

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Abstract

The invention discloses acridone derivative containing galactose, a preparation method and application thereof, and belongs to the technical field of drug synthesis. The acridone derivative has the technical scheme points that the specific structure of acridone derivative is as follows. The invention further discloses a preparation method of the acridone derivative containing galactose, and application of the acridone derivative containing galactose to preparation of anti-cancer drugs. The method has the advantages that the method is simple to operate and wild in reaction conditions, ensures that adopted reagents are all industrial common reagents, is suitable for large-scale industrial preparation, pollution-free in synthesis steps, and less in by-products; the formed acridone derivativehas excellent biological activity and anti-cancer activity, and has good commercial application value.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a class of acridone derivatives containing galactose and a preparation method and application thereof. Background technique [0002] As we all know, cancer is a disease that the public is most worried about, and it is in the leading position among all life-threatening diseases. Its morbidity and mortality are extremely high. In developed countries, the cancer mortality rate is twice that of developing countries. At present, the conventional methods for treating cancer include surgery, chemotherapy, and biological therapy. These methods have certain therapeutic effects, but there are also many disadvantages. They cannot completely eliminate cancer cells, and the curative effect on prolonging the survival of patients is not very satisfactory. Most of the existing anti-tumor drugs have certain drug resistance and side effects. Therefore, it is urgent to explor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00A61P35/00
CPCA61P35/00C07H1/00C07H15/26
Inventor 毕晶晶夏丁丁郝玉伟张月丽汪艺青陈长坡张贵生
Owner HENAN NORMAL UNIV
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