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Mono-chloride-dimethylsulfoxide-6-hydroxide radical oxidation iso-aporphine platinum (II) and synthesizing method and application thereof

A technology of dimethyl sulfoxide and hydroxyl oxidation, which is applied in the field of medicine, can solve problems such as synthetic methods and applications that have not yet been seen, and achieve significant in vitro anti-tumor activity and good medicinal value.

Inactive Publication Date: 2013-12-04
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Simultaneously, oxidized isoaporphine is also a kind of excellent organic ligand, however, there has not yet been seen that 6-hydroxyl oxidized isoaporphine and dichloro bis(dimethyl sulfoxide) combined with platinum (II) Relevant reports on the synthesis method and application of monochloro·dimethylsulfoxide·6-hydroxyloxidized isoaporphine platinum(II)

Method used

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  • Mono-chloride-dimethylsulfoxide-6-hydroxide radical oxidation iso-aporphine platinum (II) and synthesizing method and application thereof
  • Mono-chloride-dimethylsulfoxide-6-hydroxide radical oxidation iso-aporphine platinum (II) and synthesizing method and application thereof
  • Mono-chloride-dimethylsulfoxide-6-hydroxide radical oxidation iso-aporphine platinum (II) and synthesizing method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0035]Weigh 6-hydroxylated isoaporphine and dichlorobis(dimethylsulfoxide) platinum (II) in the same amount, 1 mmol each, and dissolve 6-hydroxylated isoaporphine in 50 mL of 95 % (volume) in methanol, dichlorobis(dimethylsulfoxide) platinum (II) was dissolved in 20mL of water, the two solutions were mixed, 2mL dimethylsulfoxide was added to the mixed solution, at 70°C After reacting for 24 hours, concentrate and evaporate to remove most of the solvent (80% of the solvent addition), cool to room temperature, stand still, and separate out a reddish-brown solid, separate the solid, and dry to obtain a reddish-brown solid product (90% yield) .

[0036] 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:

[0037] (1) Infrared spectrum, its spectrogram is as foll...

Embodiment 2

[0048] Weigh the same amount of 6-hydroxyisoaporphine and dichlorobis(dimethylsulfoxide) platinum (II), each 1mmol, dissolve 6-hydroxyisoaporphine in 100mL of 70 % (volume) ethanol, dichlorobis(dimethylsulfoxide) platinum (II) was dissolved in 50mL of 40% (volume) methanol, the two solutions were mixed, and the resulting mixed solution was reacted at 60°C for 4 Hours, concentrated and evaporated to remove most of the solvent (85% of solvent addition), cooled to room temperature, left standstill, a reddish-brown solid was separated out, and dried to obtain a reddish-brown solid product with a yield of 60%.

Embodiment 3

[0050] Weigh 6-hydroxylated isoaporphine and dichlorobis(dimethylsulfoxide) platinum (II) in the same amount, 1 mmol each, and dissolve 6-hydroxylated isoaporphine in 50 mL of 95 % (volume) methanol and 95% (volume) ethanol (the volume ratio of methanol and ethanol is 1:1), dissolve dichlorobis(dimethylsulfoxide) platinum (II) in 20mL In the mixed solution of water and methanol (the volume ratio of water and methanol is 1:5), mix the two solutions, add 2mL dimethyl sulfoxide to the mixed solution, react at 80°C for 48 hours, concentrate and evaporate to remove most of the solvent (95% of the amount of solvent added), cooled to room temperature and left to stand, a reddish-brown solid was precipitated, and the solid was separated and dried to obtain monochlorodimethylsulfoxide 6-hydroxyloxyisoapomorphine platinum (II ), the yield was 80%.

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Abstract

The invention discloses a novel platinum (II) coordination compound of an oxidation iso-aporphine alkaloid (namely mono-chloride-dimethylsulfoxide-6-hydroxide radical oxidation iso-aporphine platinum (II)) and a synthesizing method and application of the mono-chloride-dimethylsulfoxide-6-hydroxide radical oxidation iso-aporphine platinum (II). According to the coordination compound, 6-hydroxide radical oxidation iso-aporphine and dichloro-dimethylsulfoxide platinum (II) which are equal in amount of substance are weighed and dissolved in a polar solvent, and a target product is obtained after a heating reaction or a reflux reaction; in detail, a solution method can be used for synthesizing, and meanwhile a solvothermal method can be used for synthesizing. Proliferation inhibition, on HepG2, SK-OV-3, SK-OV-3 / DDP, BEL-7404, T-24 and other human tumor cell stains, of the coordination compound is investigated, the result shows that the novel platinum coordination compound has obvious anti-tumor activity in vitro and good potential medicinal value and is expected to be used for preparation of kinds of anti-tumor drugs. The chemical structural formula of the coordination compound is as follows (please find the formula in the specification).

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a platinum (II) complex of oxidized isoaporphine alkaloids, i.e. monochloro-dimethyl sulfoxide 6-hydroxyl-oxidized isoaporphine platinum (II) and its synthetic methods and applications. Background technique [0002] Cancer (mainly referring to malignant tumors) is one of the most serious diseases that endanger human health. The most common and serious malignant tumors in my country mainly include: breast cancer, cervical cancer, lymphoma, leukemia, lung cancer, liver cancer and other types (FarrellN, etal.CancerRes.,1992), while anti-tumor drugs are gradually developed along with the great threat of cancer to human health. After decades of research and development by scientific researchers, different types of anti-tumor drugs with different efficacy characteristics and different mechanisms of action have been launched and applied in clinical treatment and adjuvant therapy. Amon...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
Inventor 陈振锋梁宏刘延成覃其品
Owner GUANGXI NORMAL UNIV
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