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Compound with antitumor activity, and preparation method and application thereof

A technology of anti-cancer activity and compounds, applied in organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of poor solubility and curative effect of platinum (IV) compounds, achieve strong killing effect, reduce The effect of toxicity and good killing effect

Active Publication Date: 2017-12-01
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in terms of curative effect, it is far from cisplatin and carboplatin, because it is difficult for platinum (IV) compounds to avoid premature reduction in the blood circulation, so they reach less of the lesion, and platinum (IV) ) compound has extremely poor solubility, which brings difficulties to clinical application, so it is necessary to further modify it in order to improve its solubility, curative effect and accumulation amount to the lesion site, etc.

Method used

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  • Compound with antitumor activity, and preparation method and application thereof
  • Compound with antitumor activity, and preparation method and application thereof
  • Compound with antitumor activity, and preparation method and application thereof

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preparation example Construction

[0037] The present invention also provides a preparation method of a compound with anticancer activity, comprising:

[0038] A) reacting a platinum (II) compound with hydrogen peroxide to obtain a platinum (IV) compound;

[0039] B) reacting the platinum (IV) compound obtained in step A) with succinic anhydride to obtain a platinum (IV) complex containing one or two carboxyl groups in the axial direction;

[0040] C) dehydrating lactobionic acid in a reaction solvent to obtain lactone;

[0041] D) reacting the lactose lactone obtained in step C) with ethylenediamine to obtain lactose, ie, lactosamine, obtained by functionalizing the amino group;

[0042] E) reacting the platinum (IV) complex obtained in step B) with the lactosamine obtained in step D) in the presence of a condensing agent to obtain compounds represented by the structures of formulas (I) and (II);

[0043] According to the present invention, the compound represented by the formula (I) provided by the present in...

Embodiment 1

[0079] The compound shown in formula (I) structure is synthesized

[0080] Cisplatin (600 mg, 2 mmol) was placed in a reaction flask, 10 mL of 30% hydrogen peroxide was added, and after stirring for 5 h at room temperature in the dark, the hydrogen peroxide was removed by filtration to obtain Cisplatin (IV) (NH 3 ) 2 -(OH) 2 yellow powder.

[0081] The resulting Cisplatin(IV)(NH 3 ) 2 -(OH) 2 (334mg, 1mmol) and succinic anhydride (100mg, 1mmol) were dispersed in a dry DMSO solvent, and the reaction was fully stirred at 30°C for 12h, then settled with ether, filtered to obtain a solid and vacuum-dried to obtain a light yellow solid powder Cisplatin(IV)(NH3 ) 2 -(OH)(COOH).

[0082] Disperse lactobionic acid (1g) in 40mL of methanol, add 0.1mL of trifluoroacetic acid, dehydrate at 65°C for 8h to form lactose lactone, drain the methanol, dissolve the lactose lactone in 40mL of methanol, add 10mL of ethylenediamine to react at room temperature for 24h , and then settled wi...

Embodiment 2

[0087] The compound shown in formula (I) structure is synthesized

[0088] Put cisplatin (600mg, 2mmol) in the reaction flask, then add twice the equivalent of silver nitrate (679.48mg, 4mmol), react at 65°C for 12h, then filter the white precipitate, and add 4 times the equivalent of azide to the filtrate Sodium (520mg, 8mmol), react at room temperature for 4 hours, filter to obtain the filter cake, disperse with 10mL of water, add 10mL of 30% hydrogen peroxide, stir at room temperature for 8h, remove the hydrogen peroxide by filtration to obtain Cisplatin (IV) (N 3 ) 2 -(OH) 2 yellow powder.

[0089] The resulting Cisplatin(IV)(N 3 ) 2 -(OH) 2 (347mg, 1mmol) and succinic anhydride (100mg, 1mmol) were dispersed in dry DMSO, and the reaction was fully stirred at 35°C for 12h, then settled with ether, filtered to obtain a solid and vacuum-dried to obtain a light yellow solid powder Cisplatin (IV)(N 3 ) 2 -(OH)(COOH).

[0090] Disperse lactobionic acid (1g) in 40mL of m...

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Abstract

The invention provides a compound with antitumor activity, and a preparation method and application thereof, and relates to the technical field of chemical compounding drugs. The compound is of a structure shown as a formula (I) or (II). The stimuli-responsive self-assembly unimolecular compound with the antitumor activity is prepared through condensation reaction between hepatic-targeting water-soluble lactose and a platinum (IV) compound. The compound has the advantages that hepatic-targeting water-soluble lactose molecules are introduced, water-solubility of the platinum (IV) compound is improved, and hydrophilic-lyophobic balance is achieved, so that the self-assembly unimolecular platinum (IV) compound is formed, cytotoxicity of the platinum (IV) compound is reduced, a compounded tetravalence platinum prodrug has amphipathy, and accumulation degree of hepatoma cells can be increased; due to platinum, activation and release of the platinum compound are benefited under the conditions of external photostimulation or intracellular reduction, and accordingly, high antitumor activity is achieved.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis of medicines, in particular to a compound with anticancer activity and its preparation method and application. 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. divalent platinum drugs. Although clinical practice has proved that cisplatin has a broad anticancer spectrum, strong effect, synergistic effect with various antineoplastic drugs, and no cros...

Claims

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Application Information

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IPC IPC(8): C07H23/00A61K31/7135A61P35/00
CPCC07H23/00
Inventor 黄宇彬周东方何沙沙李晓媛景遐斌
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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