Halogenated 8-hydroxyquinoline platinum (II) complexes and synthesis method and application thereof

A synthetic method and compound technology, applied in the field of medicine, can solve the problem of high toxicity and achieve the effects of low toxicity, good proliferation inhibitory activity, and good medicinal value

Inactive Publication Date: 2018-06-22
GUILIN NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, people such as Zhang Hairong have designed two 8-hydroxyquinoline derivatives rhodium (III) complexes, which selectively inhibit the growth of T-24 cells with high activity and IC 50 The values ​​were 13.42 and 18.91 μM, but their toxicity to normal human liver cells HL-7702 was higher, IC 50 Values ​​up to 25-30 μM (Zhang H.R.; et al. New J. Chem., 2016, 40:6005-6014.)

Method used

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  • Halogenated 8-hydroxyquinoline platinum (II) complexes and synthesis method and application thereof
  • Halogenated 8-hydroxyquinoline platinum (II) complexes and synthesis method and application thereof
  • Halogenated 8-hydroxyquinoline platinum (II) complexes and synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0027] Weigh H-ClQ and dichlorobis(dimethylsulfoxide)platinum(II) in the same amount, each 1mmol, dissolve H-ClQ in 50mL of 100v / v% methanol, and add dichloro· Di(dimethyl sulfoxide) platinum(II) was dissolved in 1.0 mL of DMSO, after the two solutions were mixed, reacted at 80°C for 12 hours, concentrated and evaporated to remove most of the solvent (85% of the solvent added) After cooling to room temperature and standing still, yellow crystals were precipitated, and the crystals were collected and dried to obtain a yellow solid product (yield 95.0%).

[0028] The products obtained in this implementation were characterized by infrared spectroscopy, nuclear magnetic resonance hydrogen / carbon spectroscopy, elemental analysis, electrospray mass spectrometry, and X-single crystal diffraction, as follows:

[0029] (1) Infrared spectrum:

[0030] IR(KBr): 3933,3846,3782,3696,3456,3011,2921,1584,1555,1500,1448,1370,1317,1268,1198,1138,1138,1026,971,947,922,865,828,771,691,537,517,438cm -1...

Embodiment 2

[0050] Weigh the same amount of H-BrQ and dichlorobis(dimethylsulfoxide) platinum(II), each 1mmol, and dissolve H-BrQ in 25mL of 75v / v% ethanol. Di(dimethylsulfoxide)platinum(II) was dissolved in 10.0mL of water. After the two solutions were mixed, they were reacted at 65°C for 24 hours, concentrated and evaporated to remove most of the solvent (70% of the solvent added). After cooling to room temperature and standing still, yellow crystals were precipitated, and the crystals were collected and dried to obtain a yellow solid product (yield 90.0%).

[0051] The products obtained in this implementation were characterized by infrared spectroscopy, nuclear magnetic resonance hydrogen / carbon spectroscopy, and electrospray mass spectrometry, as follows:

[0052] (1) Infrared spectrum:

[0053] IR (KBr): 3913,3782,3697,3463,3006,2919,1552,1494,1443,1369,1315,1272,1195,1147,1026,948,869,825,768,680,595,530,510,438cm-1.

[0054] (2) Proton nuclear magnetic resonance spectrum:

[0055] 1H NMR(5...

Embodiment 3

[0064] Weigh H-ClQ and dichloro-bis(dimethylsulfoxide)platinum(II) in the same amount, 1mmol each, and dissolve H-ClQ in 50mL of 90v / v% methanol. Di(dimethyl sulfoxide) platinum(II) was dissolved in 10 mL of 75v / v% ethanol, the two solutions were mixed, the resulting mixed solution was reacted at 45°C for 8 hours, concentrated and evaporated to remove 81% of the solvent, and then cooled After standing at room temperature, yellow crystals were precipitated, and the crystals were collected and dried to obtain a yellow solid product with a yield of 85.3%.

[0065] The product obtained in this implementation was characterized by infrared spectroscopy, nuclear magnetic resonance hydrogen / carbon spectroscopy, elemental analysis, X-single crystal diffraction and electrospray mass spectrometry, and it was determined to be the target product ClQ-Pt.

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Abstract

The invention discloses two halogenated 8-hydroxyquinoline platinum (II) complexes and a synthesis method and application thereof. The structures of the halogenated 8-hydroxyquinoline platinum (II) complexes are shown in the formula (I), and the synthesis method comprises the steps that an 8-hydroxyquinoline derivative and dichloro bis(dimethyl sulfoxide) platinum are taken and subjected to a coordination reaction in a polar solvent, and the halogenated 8-hydroxyquinoline platinum (II) complexes are obtained. It is shown through experiments carried out by an applicant that the halogenated 8-hydroxyquinoline platinum (II) complexes have good activity of inhibiting the proliferation of certain tumor cell strains and can selectively inhibit the growth of bladder cancer T-24 cells, and the apoptosis of the tumor cells is induced under the function of targetedly interfering with mitochondria; meanwhile, the toxicity of the complexes to human normal cells HL-7702 is low. The structures of the halogenated 8-hydroxyquinoline platinum (II) complexes and the structure of the 8-hydroxyquinoline derivative are shown in the following formulas (I) and (II) respectively, wherein the formulas (I)and (II) are shown in the description, and R1 represents Cl or Br.

Description

Technical field [0001] The present invention relates to the technical field of medicine, in particular to a halogenated 8-hydroxyquinoline platinum (II) complex and its synthesis method and application. Background technique [0002] As the second leading cause of death, cancer is a serious threat to human health. Every year, more than 10 million people worldwide are diagnosed with cancer. According to the World Health Organization report, in 2012, 1410 million people worldwide suffered from cancer, of which 8.2 million died of cancer. In my country, about 2.213 million people die from cancer each year, and the death rate is much higher than that of Western developed countries. According to WHO estimates, if effective prevention and treatment measures are not taken in the future, at least 15 million people worldwide will die of cancer in 2020, and 70% of these cases will occur in developing countries (Zheng Xiaohui, et al. Progress in Chemistry, 2016, 28: 1029 -1038.). Among th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/00
Inventor 邹碧群张业何瑞杰刘贤贤覃雯黄香凌
Owner GUILIN NORMAL COLLEGE
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