9-amino oxidized isoaporphine-platinum (II) complex, synthetic method and application thereof

A synthesis method and compound technology, applied in the field of medicine, can solve the problems such as the synthesis method and application of platinum (II) complexes that have not yet been discovered, the destruction of the aromatic planarity of the oxidized isoaporphine parent ring, and the influence of electron cloud density on active sites. , to achieve significant in vitro anti-tumor activity, good medicinal value, and obvious inhibitory effect.

Active Publication Date: 2016-06-15
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the oxidized isoaporphine ligands in the above complexes coordinate with metal ions (such as platinum (II)) through 1-N and 11-C on the mother ring in bidentate chelation coordination. It is believed that this somewhat disrupts the aromatic planarity of the oxidized isoaporphine mother ring, thereby affecting its electron cloud density and possible active sites; and the good aromatic planarity and electron cloud density are considered to be a targeting effect Because of the key structural factors of telomerase and telomere G-quadruplex, this is why the telomerase inhibitory activity of the above two platinum complexes is still relatively low
[0005] The applicant searched the prior art and found no relevant reports on platinum (II) complexes with 9-aminoisoaporphine as a ligand and their synthesis methods and applications

Method used

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  • 9-amino oxidized isoaporphine-platinum (II) complex, synthetic method and application thereof
  • 9-amino oxidized isoaporphine-platinum (II) complex, synthetic method and application thereof
  • 9-amino oxidized isoaporphine-platinum (II) complex, synthetic method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Accurately weigh 0.5 mmol of ligand L and 0.5 mmol of dichlorobis(dimethylsulfoxide) platinum (II), dissolve ligand L in 55 mL of 70v / v% methanol and acetonitrile (volume of methanol and acetonitrile ratio of 1:1)), dichlorobis(dimethyl sulfoxide) platinum (II) was dissolved in 2 mL of dimethyl sulfoxide and acetone (the volume ratio of dimethyl sulfoxide and acetone was 3 : 1) in the mixed solution, two kinds of solutions were mixed, and reacted 24 hours at 65 ℃, after concentrating and evaporating to remove most of solvent (85% of solvent add-on), be cooled to room temperature and stand still, separate out yellow solid product (productivity 95%).

[0042] The resulting yellow solid product is identified:

[0043] (1) Infrared spectrum, the specific spectrum characterization data are as follows:

[0044] IR(KBr):3527,3216,3110,2917,1653,1601,1494,1439,1396,1299,1222,1131,1026,977,920,843,768,716,655,590,503,441cm -1 .

[0045] (2) Proton NMR spectrogram, the specif...

Embodiment 2

[0055] The amount of accurately weighed substance is 0.5mmol of ligand L and 0.4mmol of dichlorobis(dimethylsulfoxide) platinum (II), and the ligand L is dissolved in 35mL of 85v / v% methanol and acetonitrile (methanol In the mixed solution with acetonitrile volume ratio of 20:80), dichlorobis(dimethylsulfoxide) platinum(II) was dissolved in 5mL of acetone, and the two solutions were mixed and reacted at 80°C for 48 hours , concentrated and evaporated to remove most of the solvent (90% of the added amount of solvent), cooled to room temperature and stood still, and the yellow solid target product (yield 80%) was precipitated.

Embodiment 3

[0057] The amount of accurately weighed substance is 0.5mmol of ligand L and 0.55mmol of dichlorobis(dimethylsulfoxide) platinum (II), and the ligand L is dissolved in 43mL of 60v / v% methanol and acetonitrile (methanol In the mixed solution with acetonitrile volume ratio of 0.6:99.4), dichlorobis(dimethylsulfoxide)platinum(II) was dissolved in 1mL of dimethylsulfoxide, the two solutions were mixed, and heated at 60°C The reaction was carried out for 12 hours, concentrated and evaporated to remove most of the solvent (75% of the added amount of solvent), cooled to room temperature and allowed to stand, and the target product was precipitated as a yellow solid (yield: 85%).

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Abstract

The invention discloses a 9-amino oxidized isoaporphine-platinum (II) complex, a synthetic method and an application thereof. The 9-amino oxidized isoaporphine-platinum (II) complex is prepared with 9-amino oxidized isoaporphine and dichloro bis(dimethyl sulfoxide)platinum (II) as raw materials through a coordination reaction in a polar solvent. A research result shows that the inhibition effect of the complex on telomerase reaches 56.97% and is improved significantly than those of a 1-aza-benzanthrone platinum (II) complex and 6-hydroxy oxidized isoaporphine-platinum (II) complex. The complex has significant inhibition effect on the activity of the telomerase and has excellent selectivity and significant in-vitro antitumor activity on various human tumor cell strains and a normal liver cell strain. The structure formula of the complex is represented as the formula (I).

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 9-aminooxidized isoaporphine-platinum (II) complex and a synthesis method and application thereof. Background technique [0002] Malignant tumor accounts for about 25% of the diseases in the world today, and is one of the most important diseases threatening human life. At present, chemotherapy and radiotherapy are one of the traditional methods for treating malignant tumors. Among them, several inorganic platinum-based anticancer drugs represented by cisplatin are effective on various cancer types (such as testicular cancer, uterine cancer, bladder cancer, etc.) Cancer, lung cancer, prostate cancer, etc.) have a good curative effect. However, platinum-based drugs such as cisplatin, carboplatin, oxaliplatin, leproplatin, and heptaplatin have side effects such as low water solubility, severe toxicity, and gastrointestinal reactions, and their clinical application is obviously l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/0093
Inventor 陈振锋梁宏刘延成蒙婷覃其品梁月兰伍宸旋
Owner GUANGXI NORMAL UNIV
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