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1-azabenzanthrone-platinum (II) complex as well as synthesis method and application thereof

A technology of benzanthrone and its synthesis method, which is applied in the field of medicine, can solve problems such as blank research on metal complexes, and achieve significant in vitro anti-tumor activity and good medicinal value.

Inactive Publication Date: 2013-12-18
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Oxidized isoapomorphine alkaloids have significant antitumor activity, but the research on their metal complexes is still blank

Method used

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  • 1-azabenzanthrone-platinum (II) complex as well as synthesis method and application thereof
  • 1-azabenzanthrone-platinum (II) complex as well as synthesis method and application thereof
  • 1-azabenzanthrone-platinum (II) complex as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Weigh the same amount of 1-azabenzanthrone and dichlorobis(dimethylsulfoxide) platinum (II), each 1mmol, dissolve 1-azabenzanthrone in 50mL of 100 % (volume) in methanol, dichlorobis(dimethylsulfoxide) platinum (II) was dissolved in 20mL of water, the two solutions were mixed, 2mL dimethylsulfoxide was added to the mixture, at 70°C The reaction was carried out at low temperature for 20 hours, concentrated and evaporated to remove most of the solvent (85% of the added amount of solvent), cooled to room temperature and allowed to stand, and the reddish-brown target product was precipitated (yield: 90%).

[0037] The resulting reddish-brown solid product was analyzed by infrared spectroscopy, hydrogen nuclear magnetic resonance spectroscopy, electrospray mass spectroscopy, single crystal diffraction and ultraviolet spectroscopy. The specific spectral characteristics are as follows:

[0038] (1) Infrared spectrum, its spectrogram is as follows figure 1 as shown,

[0039] ...

Embodiment 2

[0049] Weigh the same amount of 1-azabenzanthrone and dichlorobis(dimethylsulfoxide) platinum (II), each 1mmol, dissolve 1-azabenzanthrone in 60mL of 80 % (volume) ethanol, dichlorobis(dimethylsulfoxide) platinum (II) was dissolved in 20mL of 90% (volume) ethanol, the two solutions were mixed, and 8mL dimethyl Sulfoxide, reacted at 80°C for 5 hours, concentrated and evaporated to remove most of the solvent (80% of the solvent added), cooled to room temperature and stood still, and the reddish-brown target product monochloro-mono(dimethylsulfoxide) was precipitated. Mono(1-azabenzanthrone)platinum(II) (65% yield).

Embodiment 3

[0051] Weigh the same amount of 1-azabenzanthrone and dichlorobis(dimethylsulfoxide) platinum (II), each 1mmol, dissolve 1-azabenzanthrone in 100mL of 60 In a mixed solution of % (volume) methanol and 70% (volume) ethanol (volume ratio of 6:1), dissolve dichlorobis(dimethylsulfoxide) platinum (II) in 50mL of water and 100% (Volume) In the mixed solution of methanol (volume ratio 3:2), the two solutions are mixed, 10mL dimethyl sulfoxide is added to the mixed solution, reacted at 90°C for 36 hours, concentrated and evaporated to remove most of the solvent (solvent added 85% of the amount), cooled to room temperature and stood still, and the reddish-brown target product monochlorine one (dimethyl sulfoxide) one (1-azabenzanthrone) platinum (II) was precipitated (yield 75 %).

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Abstract

The invention discloses a new 1-azabenzanthrone-platinum (II) complex, i.e., monochloro.mono(dimethyl sulfoxide).mono(1-azabenzanthrone) platinum (II), as well as a synthesis method and an application thereof. The complex is prepared through the following steps: weighing equivalent amounts of 1-azabenzanthrone and dichloro-di(dimethyl sulfoxide) platinum (II); dissolving in a polar solvent; heating or performing reflux reaction to obtain a target product, wherein the synthesis can specifically be performed through a solution method or a solvothermal method. Investigation shows that the complex has anti-proliferative activity on human tumor cell strains such as HepG2, SK-OV-3, SK-OV-3 / DDP, BEL-7404, T-24 and HL-7702; the result shows that the complex has obvious in-vitro anti-tumor activity, has higher potential medicinal value and is expected to be used for preparing various anti-tumor medicaments. The chemical structural formula of the complex is shown in the specification.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a 1-azabenzanthrone-platinum (II) complex, namely monochloro-one(dimethylsulfoxide)-one(1-azabenzanthrone) Platinum (II), and its synthesis and application. Background technique [0002] At present, there are more than 4.5 million cancer patients in China. The main methods of clinical treatment of cancer are: radiotherapy, chemotherapy and surgical resection. As early as 1965, Rosenberg et al. discovered that cisplatin had a strong growth inhibitory effect on various malignant tumors such as breast cancer, lymphoma, bladder cancer, ovarian cancer, testicular cancer, and leukemia (Rosenberg, B.; et al. Nature, 1965, 205:698-699.). This work created a precedent for inorganic metal complexes to become anticancer drugs, and laid the foundation for bioinorganic medicinal chemistry (Zhou Tianze, Hu Dingxi, works. Element Elite. Beijing: Ocean Press, 2000, 114.). Although chemothera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
Inventor 陈振锋梁宏刘延成覃其品
Owner GUANGXI NORMAL UNIV
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