Anti-prostate cancer compound and preparation method thereof

An anti-prostate cancer, prostate cancer technology, applied in anti-tumor drugs, organic chemistry, drug combination and other directions, can solve the problems of low drug activity, large toxic and side effects, etc., achieves simple preparation method, mild process conditions, and is suitable for large-scale production. Effect

Inactive Publication Date: 2021-05-07
重庆知翔科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some studies have been done in the prior art, drugs such as tetrodotoxin and phenytoin have low activity and relatively large toxic and side effects, so it is necessary to develop anti-prostate cancer drugs with stronger activity and better safety

Method used

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  • Anti-prostate cancer compound and preparation method thereof
  • Anti-prostate cancer compound and preparation method thereof
  • Anti-prostate cancer compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The preparation of formula I compound, synthetic route is as follows:

[0019]

[0020] Specific steps:

[0021] Add 1.52g of compound B, 10mL of tetrahydrofuran and 10mL of thionyl chloride into a 50mL single-port reaction flask with magnetic stirring, keep stirring, and reflux for 4 hours. Excess thionyl chloride was removed under reduced pressure, 12 mL of a tetrahydrofuran solution containing 1.65 g of compound A and 1 g of 4-(N,N-dimethyl)pyridine were added, and stirred at room temperature for 10 hours. The reactant in the reaction bottle was placed in a 100mL separatory funnel, 25mL ethyl acetate was added, and 5% Na 2 CO 3 Wash twice with 25 mL of aqueous solution, then twice with 20 mL of water, and finally once with 10 mL of saturated NaCl aqueous solution. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, concentrated, purified by column chromatography, and concentrated again to obtain the compound of formula I (1.28 g). 1...

Embodiment 2

[0023] The preparation of formula II compound, synthetic route is as follows:

[0024]

[0025] Specific steps:

[0026] Add the compound of formula 1.20gb, 10mL tetrahydrofuran and 10mL thionyl chloride into a 50mL single-port reaction flask with magnetic stirring, keep stirring, and reflux for 4 hours. Excess thionyl chloride was removed under reduced pressure, 12 mL of a tetrahydrofuran solution containing 1.10 g of the compound of formula a and 1 g of 4-(N,N-dimethyl)pyridine were added, and stirred at room temperature for 10 hours. Transfer the reactants in the reaction bottle to a 100mL separatory funnel, add 25mL ethyl acetate to dilute, and dilute with 5% Na 2 CO 3 Wash twice with 25 mL of aqueous solution, then twice with 20 mL of water, and finally once with 10 mL of saturated NaCl aqueous solution. The organic layer was separated, dried over anhydrous sodium sulfate, concentrated after filtration, and purified by column chromatography to obtain the compound of...

Embodiment 3

[0027] Example 3 Biological Example

[0028] Use the MTT method to detect the activity of the above-mentioned compounds of formula I and formula II inhibiting prostate cancer DU145 cells and prostate cancer PC3 cells. For details, see CN 104098479 A. The IC50 of the compounds of formula I and formula II killing prostate cancer DU145 cells and prostate cancer PC3 cells is shown in the table 1.

[0029] The killing effect (IC50 / μM) of each compound of table 1 on prostate cancer cells

[0030]

[0031] From the results in Table 1, it can be seen that the compound of formula I of the present invention has a good inhibitory effect on prostate cancer cells, whether it is DU145 cells or prostate cancer PC3 cells.

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Abstract

The invention provides an anti-prostatic cancer compound which is used as a VGSCs inhibitor and has a good killing effect on prostatic cancer DU145 and prostatic cancer PC3 cells. The preparation method is simple, mild in process condition and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of new drug development, and in particular relates to an anti-prostate cancer compound and a preparation method thereof. Background technique [0002] Prostate cancer refers to epithelial malignant tumors that occur in the prostate. Prostate cancer is currently the second most commonly diagnosed cancer in men in developed countries worldwide. Chemotherapy has become the main treatment method for prostate cancer. Chemotherapy drugs mainly include mitoxantrone and paclitaxel. Because these drugs are expensive and have severe side effects, it is urgent to develop new anti-prostate cancer drugs. [0003] Voltage-gated sodium ion channels (VGSCs for short) are channel protein receptors with important physiological functions, which can regulate the rising segment of the action potential of excitatory cells, and are new targets for tumor chemotherapy. Studies have shown that the VGSCs blocker tetrodotoxin (tetrod...

Claims

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Application Information

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IPC IPC(8): C07D207/27C07D209/42A61P13/08A61P35/00
CPCA61P13/08A61P35/00C07D207/27C07D209/42
Inventor 不公告发明人
Owner 重庆知翔科技有限公司
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