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Platinum compound with anti-tumor activity as well as preparation method and application

A complex and platinum-based technology, applied in anti-cancer and anti-tumor applications, new tetravalent platinum complexes and their preparation, can solve the problem of less combined work

Active Publication Date: 2018-04-24
THE AFFILIATED HOSPITAL OF QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there has been extensive work on the modification of tetravalent platinum, there has been relatively little work combining natural compounds with tetravalent platinum compounds

Method used

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  • Platinum compound with anti-tumor activity as well as preparation method and application
  • Platinum compound with anti-tumor activity as well as preparation method and application
  • Platinum compound with anti-tumor activity as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The preparation of embodiment 1 hydroxy oxaliplatin (IV)

[0020]

[0021] Add 3.0 g of oxaliplatin and 70 mL of distilled water into the flask, stir to disperse them, slowly add 130 mL of 30% hydrogen peroxide dropwise into the reaction system, raise the temperature to 65°C and stir for 3 hours. The reaction was stopped, placed under cooling for crystallization for 12 hours, filtered to obtain a yellow solid, added an appropriate amount of water, heated to dissolve it, cooled and allowed to stand for crystallization for 12 hours, and filtered to obtain white crystals (2.5 g).

Embodiment 2

[0022] The preparation of the monohydroxy oxaliplatin (IV) that embodiment 2 carboxylic acid group replaces

[0023]

[0024] Add 1.6 g of the compound prepared in Example 1 and 0.79 g of hexanoic anhydride to a round bottom flask, add 70 mL of anhydrous DMSO under nitrogen protection, stir and react at 35°C for 4 days, evaporate DMSO under reduced pressure, add acetone, and precipitate The white solid powder was suction filtered and washed 3 times with acetone to obtain a white solid product (1.5 g).

Embodiment 3

[0025] Embodiment 3 target product is synthesized

[0026]

[0027] Add 0.01 mol of the tetravalent platinum intermediate prepared in Example 2 and 0.02 mol of galloyl chloride protected by whole benzyl groups into the flask, protect with nitrogen and add anhydrous acetone, stir at room temperature for 12 to 36 hours, and stop the reaction. Acetone was removed by concentration, and the product was obtained by column chromatography. Dissolve the product in an appropriate amount of anhydrous dichloromethane, stir at -78°C for 15 minutes, slowly add 1M boron trichloride / dichloromethane solution dropwise to the reaction solution, continue stirring for 2 hours, and stop the reaction. The solvent was distilled off under reduced pressure, and the residual solid was washed three times with petroleum ether, and separated by column chromatography to obtain the target product, which was designated as compound 1.

[0028] The product is a light yellow solid; 1 H NMR (400MHz, DMSO-d ...

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PUM

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Abstract

The invention provides a tetravalence platinum anti-tumor compound based on gallic acid. A carboxylic acid ligand part is adjusted to find out that the platinum compound not only has relatively high anti-tumor activity, but also has certain tumor cell selectivity; the platinum compound also has an inhibition effect on drug-resisting cells.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a novel tetravalent platinum complex, its preparation method and its application in anticancer and antitumor. Background technique [0002] Since cisplatin was found to have anticancer activity in 1967, the application and research of platinum metal anticancer drugs have developed rapidly, and now it has formed the first generation cisplatin, the second generation carboplatin and the third generation oxali Platinum-dominated bivalent platinum-based cancer clinical drugs. At present, divalent platinum-based anticancer drugs have become an indispensable chemotherapeutic drug for clinical cancer treatment. However, divalent platinum compounds have common characteristics such as poor stability, low bioavailability, inability to take orally, strong toxic and side effects (such as nephrotoxicity, ototoxicity, neurotoxicity, etc.), poor water solubility, serious cross-resistance, and...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0093
Inventor 金建德
Owner THE AFFILIATED HOSPITAL OF QINGDAO UNIV
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