Calycosin derivative as well as synthesis method and application thereof

A synthesis method and reaction technology, applied in the field of medicine, can solve problems such as unclear targets and large effective concentrations

Active Publication Date: 2020-05-19
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Existing studies have shown that calycosin has the functions of anti-oxidative stress, anti-virus and regulation of cell apoptosis, but its disadvantage is that its effective concentration is relatively large, and the target is not clear
At present, there is no relevant report on calycosin derivatives that can simultaneously inhibit ER-positive breast cancer cells and ER-negative breast cancer cells

Method used

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  • Calycosin derivative as well as synthesis method and application thereof
  • Calycosin derivative as well as synthesis method and application thereof
  • Calycosin derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Compound shown in synthetic formula (I) according to following synthetic route

[0040]

[0041] Among them, the chemical name of compound 1 is: 7-hydroxy-3-(3-hydroxy-4-methoxy)-4H-benzopyran-4-one, and compound 2 is ethyl chloroacetate.

[0042] The specific synthesis method is:

[0043] Take 1g (3.52mmol) of compound 1 (Caleoisoflavone) in a 50ml round bottom flask and dissolve it with 40ml of acetone, then add 3g of anhydrous K 2 CO 3 and 0.5gNaI, stirred at room temperature for 1h, then added dropwise 0.91g (7.43mmol) of compound 2 (ethyl chloroacetate), then placed in a 45°C water bath and stirred and refluxed for 4h (TCL to monitor the reaction, the developer was chloroform:methanol=60: 1, volume ratio); then stop heating and continue stirring until cooling. Add ice water to the cooled reactant, filter, collect the precipitate, dissolve the precipitate with ethyl acetate and dry with anhydrous sodium sulfate, evaporate the resulting solution t...

Embodiment 2

[0049] Embodiment 2: compound shown in synthetic formula (I)

[0050] Repeat Example 1, the difference is that with anhydrous Na 2 CO 3 instead of anhydrous K 2 CO 3 , replace NaI with KI, and change the reaction to 55°C.

[0051] Finally, a pale yellow solid was obtained, 70.21%.

[0052]The product obtained in this example was characterized by proton nuclear magnetic resonance spectrum and carbon spectrum, and was determined to be the compound shown in formula (I).

Embodiment 3

[0053] Embodiment 3: compound shown in synthetic formula (I)

[0054] Repeat Example 1, except that DMF is used instead of acetone and triethylamine is used instead of anhydrous K 2 CO 3 , and the reaction was carried out at 40°C.

[0055] Finally, a pale yellow solid was obtained, 23.18%.

[0056] The product obtained in this example was characterized by proton nuclear magnetic resonance spectrum and carbon spectrum, and was determined to be the compound shown in formula (I).

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Abstract

The invention discloses a calycosin derivative as well as a synthesis method and application thereof. The synthesis method of the calycosin derivative mainly comprises the following steps of: dissolving a compound 1 and a compound 2 in an organic solvent, adding an acid-binding agent, and reacting under a heating condition to obtain a target crude product. Experimental results of the applicant show that the calycosin derivative can inhibit proliferation of ER positive breast cancer cells and ER negative breast cancer cells at the same time; along with the increase of the concentration of the derivative, the proliferation rate of breast cancer cells is gradually reduced, the inhibition effect is the most obvious at high concentration, and no influence is caused to normal breast cells MCF-10A.

Description

technical field [0001] The invention relates to a calycosin derivative and its synthesis method and application, belonging to the technical field of medicine. Background technique [0002] Globally, according to research reports, breast cancer is one of the most common malignant cancers in women, and the incidence of breast cancer also ranks first, accounting for about 29% of new malignant tumors in women. The second place has become the number one risk factor that threatens the safety of women's lives. According to statistics, as of 2016, the number of patients with breast cancer in my country has exceeded 500,000, and the age of onset is decreasing year by year, showing a trend of younger age, while the incidence and mortality are increasing year by year. The highest age group is 35-49 years old. Scholars at home and abroad have conducted extensive research on breast cancer risk factors and pathogenesis factors, and put forward different views, and there are many inconsis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/352A61P35/00
CPCC07D311/36A61P35/00
Inventor 陈健王勇李鑫任倩瑶秦俭陈晓宇
Owner GUILIN MEDICAL UNIVERSITY
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