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Phthalocyanine-aryl ruthenium compound and preparation method and application thereof

A ruthenium compound and aryl technology, applied in the field of monochloro-β-1-2-ethoxy-phthalocyanine-methylisopropylphenylruthenium and its preparation, can solve the problem of no tumor inhibitory effect and cross drug resistance In order to achieve the effects of low cost, easy-to-obtain raw materials and simple preparation methods

Active Publication Date: 2017-04-26
WUHAN OPTICS VALLEY YATAI PHARM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of cisplatin also has certain shortcomings. It has no inhibitory effect on certain tumors and is prone to cross-resistance with other platinum agents.
In addition, cisplatin has a variety of side effects, such as nephrotoxicity, peripheral neurotoxicity, bone marrow toxicity, hematological toxicity and emetogenicity, etc.

Method used

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  • Phthalocyanine-aryl ruthenium compound and preparation method and application thereof
  • Phthalocyanine-aryl ruthenium compound and preparation method and application thereof
  • Phthalocyanine-aryl ruthenium compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A phthalocyanine-arylruthenium compound:

[0032] 1) The chemical name of the phthalocyanine-arylruthenium compound is monochloro-β-one-2-(2-diethylamine)ethoxy-phthalocyanine-methylisopropylphenylruthenium(II);

[0033] Structural formula:

[0034]

[0035] 2) Physical and chemical properties: monochloro-β-1-2-(2-diethylamine)ethoxy-phthalocyanine-methylisopropylphenylruthenium(II), red crystal, easily soluble in water and organic solvent, its H NMR spectrum data is 1 H NMR: (ppm, CDCl 3 )δ=0.97(3H,s),1.13(6H,d,J=6.9Hz),2.35(3H,s),2.77-2.97(6H,m,J=6.1Hz),3.12(1H,m,J = 6.9Hz), 3.46 (2H, d, J = 5.9Hz), 6.77-7.90 (15H, m, J = 6.1Hz).

Embodiment 2

[0037] The preparation method of a chloro-β-one-2-(2-diethylamine) ethoxy-phthalocyanine-methyl isopropyl phenyl ruthenium (II), comprises the following steps:

[0038] 1) 0.366g ruthenium weight content is 37% RuCl 3 ·xH 2 O and 3ml of γ-terpinene with a purity of 95% were dissolved in 10ml of absolute ethanol, heated to reflux and stirred for 6 hours, and left to separate out to obtain dichloro-dichloro-bis-methylcumene diruthenium (II) .

[0039]

[0040] 2) Weigh 0.095g of β-1-nitro-phthalocyanine and 0.12g of 2-(2-diethylamine)ethanol, dissolve them in 10ml of DMF solution, react at 80°C for 6 hours under the protection of nitrogen, and then stand to precipitate to obtain β- Mono-2-(2-diethylamine)ethoxy-phthalocyanine.

[0041]

[0042] 3) Dissolve 30 mg of β-one-2-(2-diethylamine) ethoxy-phthalocyanine and 12 mg of dichloro-di-methylcumene diruthenium (II) in 8 ml of Water and ethanol, heated and stirred to reflux for 6 hours. After the reaction was completed,...

Embodiment 3

[0044] In vitro cytotoxicity assays were performed using the MTT method. The organometallic ruthenium compound obtained in Example 1 was reacted with the ovarian cancer A2780 cell line for 72 hours respectively, and the results are shown in Table 1.

[0045] Table 1 organometallic ruthenium compounds to the half maximal effective concentration (IC) of tumor cell lines 50 )

[0046] cell line A2780 (protect from light) A2780 (illumination) IC 50 (μmol / mL)

6.0±0.8 1.3±0.3

[0047] In vitro tumor cell inhibitory activity experiments show that a chlorine-beta-one-2-(2-diethylamine) ethoxy-phthalocyanine-methylisopropylphenylruthenium (II) compound of the present invention is effective on ovarian cancer The A2780 cell line has a significant inhibitory effect, and its inhibitory effect is significantly enhanced under visible light irradiation.

[0048] From the above results, it can be seen that the phthalocyanine-aryl ruthenium compound of the present...

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Abstract

The invention discloses phthalocyanine-aryl ruthenium compound, namely mono-Beta-mono-2-(2-diethylamine)ethoxy-phthalocyaninemonomethylcumeneruthenium monochloride (II). The invention also discloses a preparation method of the phthalocyanine-aryl ruthenium compound; the preparation method comprises: 1) dissolving RuCl3.xH2O and Gamma-terpinene in absolute ethyl alcohol, heating for refluxing and stirring, standing and separating out to obtain dichloro-di-methylcumeneruthenium dichloride (II); 2) dissolving Beta-mono-nitro-phthalocyanine and 2-(2-diethylamine)ethanol in DMF (dimethyl formamide) solution, reacting under nitrogen protection, and standing and separating out to obtain Beta-mono-2-(2-diethylamine)ethoxy-phthalocyanine; 3) dissolving the Beta-mono-2-(2-diethylamine)ethoxy-phthalocyanine and the dichloro-di-methylcumeneruthenium dichloride (II) in absolute ethyl alcohol, heating and stirring for refluxing, reacting, adding n-hexane, and separating out red crystal which is the product mono-Beta-mono-2-(2-diethylamine)ethoxy-phthalocyaninemonomethylcumeneruthenium monochloride (II). The invention also discloses application of the phthalocyanine-aryl ruthenium compound.

Description

technical field [0001] The invention belongs to the technical field of medicines, and relates to a phthalocyanine-aryl ruthenium compound and its preparation method and application, in particular to a monochloro-β-1-2-(2-diethylamine)ethoxy-phthalocyanine Ruthenium(II)-methylcumene, its preparation method and use. Background technique [0002] At present, cisplatin has become one of the three most widely used drugs for cancer treatment in the world, with annual sales in the United States reaching nearly 500 million US dollars. However, the use of cisplatin also has certain shortcomings. It has no inhibitory effect on certain tumors and is prone to cross-resistance with other platinum agents. In addition, cisplatin has a variety of side effects, such as nephrotoxicity, peripheral neurotoxicity, bone marrow toxicity, hematological toxicity, and emetogenicity. Therefore, finding new anti-tumor drugs with high efficiency, low toxicity and no cross-resistance has always been a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P15/00A61P35/00
CPCC07F15/0046
Inventor 苏炜李培源肖琦黄珊
Owner WUHAN OPTICS VALLEY YATAI PHARM RES INST CO LTD
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