Compound having anticancer activity and preparation method

An anti-cancer activity and compound technology, applied in the field of compounds with anti-cancer activity and their preparation, can solve the problems of insignificant advantages of Satraplatin and the need for further improvement of anti-tumor activity, so as to improve the anti-cancer effect and reverse cisplatin resistance. the effect of reducing cytotoxicity

Active Publication Date: 2014-02-19
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, in terms of curative effect, compared with cisplatin and carboplatin, Satraplatin has no outstanding advantages except oral activity, and its antitumor activity needs to be further improved

Method used

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  • Compound having anticancer activity and preparation method
  • Compound having anticancer activity and preparation method
  • Compound having anticancer activity and preparation method

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preparation example Construction

[0034] The present invention also provides a preparation method of a compound with anticancer activity, comprising:

[0035] A) reacting platinum (II) compound with hydrogen peroxide to obtain platinum (IV) compound;

[0036] B) reacting the platinum (IV) compound obtained in step A) with demethylcantharidin to obtain a platinum (IV) complex with demethylcantharidin as a ligand;

[0037] C) react the platinum (IV) complex obtained in step B) with N-tert-butoxycarbonylpiperazine in the presence of a condensing agent to obtain the compound shown in the structure of formula (I); wherein, the R5 is tert-butoxycarbonyl;

[0038] Or react the complex of platinum (IV) and demethylcantharidin obtained in step B) with N-methylpiperazine in the presence of a condensing agent to obtain the compound shown in the structure of formula (I); wherein , the R5 is a methyl group.

[0039] The compound represented by the formula (I) provided by the present invention is synthesized in three ste...

Embodiment 1

[0061] Put cisplatin (600mg, 2mmol) in a flask, then add 10mL of 30% hydrogen peroxide, stir at room temperature in the dark for 8 hours, remove the hydrogen peroxide by filtration to obtain Cisplatin(IV)-(OH) 2 yellow powder.

[0062] The resulting Cisplatin(IV)-(OH) 2 (334mg, 1mmol) and demethylcantharidin (336mg, 2mmol) were dissolved in dry DMF, and stirred at 70°C for 12h. Then drain the DMF in the system, dissolve the remaining substance with acetone, and filter off the insoluble matter, concentrate the filtrate and settle the ether, filter to obtain a solid and vacuum dry it to obtain a white solid powder Cisplatin (IV)-(DMC) 2 .

[0063] The resulting Cisplatin(IV)-(DMC) 2 (335mg, 0.5mmol) and N,N'-carbonyldiimidazole (162mg, 1mmol) were dissolved in dry DMF and stirred at 40°C for 2h. Then N-tert-butoxycarbonylpiperazine (186mg, 1mmol) was added, and the stirring reaction was continued for 24h. After the reaction, the DMF in the system was vacuum-dried, and then ...

Embodiment 2

[0069] Put cisplatin (600mg, 2mmol) in a flask, then add 10mL of 30% hydrogen peroxide, stir at room temperature in the dark for 8 hours, remove the hydrogen peroxide by filtration to obtain Cisplatin(IV)-(OH) 2 yellow powder.

[0070] The resulting Cisplatin(IV)-(OH) 2 (334mg, 1mmol) and demethylcantharidin (1009mg, 6mmol) were dissolved in dry DMF, and stirred at 70°C for 24h. Then drain the DMF in the system, dissolve the remaining substance with acetone, and filter off the insoluble matter, concentrate the filtrate and settle the ether, filter to obtain a solid and vacuum dry it to obtain a white solid powder Cisplatin (IV)-(DMC) 2 .

[0071] The resulting Cisplatin(IV)-(DMC) 2 (335mg, 0.5mmol) and N,N'-carbonyldiimidazole (203mg, 1.25mmol) were dissolved in dry DMF and stirred at 60°C for 12h. Then N-tert-butoxycarbonylpiperazine (372.5mg, 2mmol) was added, and the stirring reaction was continued for 72h. After the reaction, the DMF in the system was vacuum-dried, an...

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Abstract

The invention provides a compound having anticancer activity, which is obtained by cooperation of Norabieta cantharidin and platinum (IV) and modification of a piperazine derivative. The compound is characterized in that a Norabieta cantharidin piperazine derivative ligand is introduced, thereby cytotoxicity of a platinum (IV) compound is reduced, and high antineoplastic activity is provided. The result of the cytotoxicity experiments shows that the provided platinum (IV) compound has less destruction to normal mice fibroblast L929, but has good killing effect to cancer cells such as human breast cancer MCF-7 cell, human cervical carcinoma HeLa cell and human lung adenocarcinoma A549 cell, so that the compound having anticancer activity is capable of reducing the system toxicity and having equal anticancer activity with cisplatin. The compound having anticancer activity has good killing effect by aiming at cisplatin resistance human lung adenocarcinoma A549/DDP cell. Therefore, the toxicity is reduced, the cisplatin resistance can be reversed, and anticancer effect of the platinum medicines can be increased.

Description

technical field [0001] The invention relates to the technical field of chemically synthesized drugs, in particular to a compound with anticancer activity and a preparation method thereof. Background technique [0002] Since the discovery of cisplatin's anticancer activity in 1967, the research and application of platinum-based metal anticancer drugs have been greatly developed. At present, thousands of platinum series compounds have been screened, and dozens of them have entered clinical research. , several have been approved to enter the market. [0003] Among them, platinum (II) has been widely used in chemotherapy, such as cis-dichlorodiammine platinum (II), also known as cisplatin (cisplatin), which is a periodic non-specific drug and is the most clinically used drug. A divalent platinum-based drug that can bind to DNA to form a cross bond, thereby destroying the replication function of DNA. Clinical practice has proved that cisplatin has a broad anticancer spectrum, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00
Inventor 黄宇彬周东方王明哲李晓媛景遐斌谢志刚
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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