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Ruthenium-containing coordination compound and preparation method thereof

A complex and inhibitor technology, applied in the field of ruthenium-containing complexes and their preparation, can solve the problems of no "single-molecule multi-target" anti-tumor drug research reports, stay in laboratory research, toxic and side effects, etc. The effect of reducing the possibility of drug resistance, improving water solubility, and reducing toxic side effects

Inactive Publication Date: 2010-11-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the toxic side effects of the cytotoxic (alkylating) units in this class of combinatorial molecules have kept their research at the laboratory stage
[0005] Literature research and patent novelty searches show that, so far, there are no research reports on "single-molecule multi-target" anti-tumor drugs based on protein kinase inhibitors and cytotoxic metal complexes at home and abroad.

Method used

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  • Ruthenium-containing coordination compound and preparation method thereof
  • Ruthenium-containing coordination compound and preparation method thereof
  • Ruthenium-containing coordination compound and preparation method thereof

Examples

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preparation example Construction

[0018] According to the present invention, the preparation method of the complex containing ruthenium comprises the following steps:

[0019] (1) In the mixed solution of liquefied ammonia and lower alcohol, aromatic hydrocarbons are mixed with alkali metals to obtain dihydroaromatic hydrocarbons;

[0020] (2) contacting the dihydroaromatic hydrocarbon with the ruthenium halide in the first organic solvent, and the conditions of the contact reaction make the reaction obtain the ruthenium halide arene dimer;

[0021] (3) The ruthenium halide arene dimer that step (2) obtains is contacted with the chelating ligand that contains two coordination atoms in the second organic solvent, and the chelating ligand that contains two coordination atoms is selected from From one of alkyldiamine, 8-hydroxyquinoline and its derivatives, and phenanthroline and its derivatives, the conditions of the contact reaction make the ruthenium in the ruthenium halide arene dimer and the two in the chela...

Embodiment 1

[0035] This example serves to illustrate the preparation of the ruthenium-containing complexes of the present invention.

[0036]

[0037] (1) In the mixed solution of liquid ammonia and ethanol, at -78°C, mix the aromatic hydrocarbon and metallic sodium for 1 hour (the molar ratio of liquid ammonia, ethanol, aromatic hydrocarbon and sodium is 250:10:1:5), to obtain Dihydrogenated aromatic hydrocarbons; the aromatic hydrocarbons are respectively benzene, biphenyl, isopropyl-p-toluene, and benzocyclopentane; then the reaction product is subjected to vacuum distillation at 50-150° C. to remove the solvent and some unreacted raw materials, Obtained by nuclear magnetic resonance analysis, in the reaction product mixture, the purity of dihydroaromatics is about 70% by weight;

[0038] (2) The reaction product mixture containing dihydroaromatics and ruthenium chloride are contacted in ethanol, wherein, the consumption of the reaction product mixture containing dihydroaromatics ma...

Embodiment 2

[0055] This example serves to illustrate the preparation of the ruthenium-containing complexes of the present invention.

[0056]

[0057] The ruthenium chloride arene dimer (prepared in Example 1) with a molar ratio of 1:1 was contacted with 8-hydroxyquinoline and its derivatives at 35° C. in methanol solution for 10 hours, and the ruthenium chloride The total amount of arene dimer and 8-hydroxyquinoline and its derivatives is 100 mg as a basis, and the amount of methanol is 30 ml, and then recrystallized in ethanol solution.

[0058] The benzene-ruthenium series complexes were obtained respectively: LQ2009, LQ2010, LQ2011 and LQ2012;

[0059] p-cymene-ruthenium complexes: LQ2013, LQ2014, LQ2015 and LQ2016.

[0060] The compounds prepared above were characterized by nuclear magnetic resonance and mass spectrometry respectively:

[0061] LQ2009: C 15 h 12 NORuCl, calc.MW=358.8, ESI-MS (m / z): [M-Cl] + =323.3

[0062] 1 H NMR: (Deuterated DMSO) δ (ppm): 9.315 (d, 1H), ...

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Abstract

The invention relates to a ruthenium-containing coordination compound. The ruthenium-containing coordination compound is a coordination compound expressed by ARu(X'Y')Z or [ARu(XY)Z]+B-, wherein A is arene; XY is one of dialkyl amine, and feiluolin and derivatives thereof; the X'Y' is one of 8-hydroxyguinoline and a derivative thereof; Z is one of halogen, -SCN, -N3,-SCH3, -SH, -COOH, pyridyl, pyridyl substituted by one or more groups in C1-C3 alkyl and tyrosine kinase inhibitor with a single coordination atom; and B- is PF6- or BF4-. The new ruthenium-containing coordination compound can effectively act on DNA, or substitute a high-selectivity protein kinase inhibitor or a derivative thereof for one or more of ligands in the cytotoxicity organic metal ruthenium coordination compound, and can act on the protein kinase (or protein phosphatase) and a multi-target point combining molecular anti-tumor compound of DNA at the same time.

Description

technical field [0001] The invention relates to a complex containing ruthenium and a preparation method thereof. Background technique [0002] Since the first report in 1969 that cisplatin (Cisplatin, also known as cisplatin) has a strong inhibitory effect on animal tumors, scientists have paid more attention to the anti-tumor research of metal complexes. In recent years, it has been confirmed that in addition to platinum, complexes such as ruthenium, rhodium, gallium, germanium, and tin also have anti-tumor activity, and the inhibitory activity of organometallic ruthenium complexes on ovarian cancer, non-small cell lung cancer and other cancer cells is comparable to that of cisplatin , and has no cross-resistance with cisplatin, and has low toxicity and side effects, so it has received widespread attention. The mechanisms of action of organometallic ruthenium antitumor compounds and cisplatin are not exactly the same, but they both use DNA as the ultimate target and belong...

Claims

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Application Information

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IPC IPC(8): C07C211/09C07D215/30C07D471/04C07F15/00A61K31/4745A61K31/47A61K31/132A61K31/28A61P35/00
Inventor 汪福意罗群吕爽吴魁胡文兵纪丽云韩玉苗
Owner INST OF CHEM CHINESE ACAD OF SCI
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