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Copper complex of phenanthroline derivatives and preparation method and application thereof

A technology of o-phenanthroline and copper complexes, applied in the direction of copper organic compounds, drug combinations, 1/11 group organic compounds without C-metal bonds, etc., to achieve high yield, good water solubility and fat solubility, excellent The effect of inhibition

Inactive Publication Date: 2011-08-10
CAPITAL NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, so far, there is no single- and multiple-substituted copper complexes of o-phenanthroline derivatives as clinical drugs for the prevention and treatment of cancer and tumors.

Method used

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  • Copper complex of phenanthroline derivatives and preparation method and application thereof
  • Copper complex of phenanthroline derivatives and preparation method and application thereof
  • Copper complex of phenanthroline derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of complex Z1

[0038] 0.29g Cu(NO 3 ) 2 ·3H 2 O and 0.174g of 2,9-dimethyl-1,10-phenanthroline were sequentially added into 10mN,N-dimethylacetamide (DMA) and 50ml of anhydrous methanol, stirring continuously. After reacting for 8 hours, it was filtered, the mother liquor was diffused with diethyl ether, and allowed to stand at room temperature, and green blocky crystal Z1 was obtained after a few days.

[0039] The molecular formula of Z1 compound is: {Cu[2,9-CH 3 -(1,10-Phen)](NO 3 ) 2 (DMA)}, i.e. 1 2,9-CH 3 -(1,10-Phen), 2 NO 3 and 1 DMA coordinated to 1 Cu.

[0040] Elemental analysis (%): Calculated (exp.): C 44.77 (44.66); H 4.35 (3.30); N 14.51 (14.46); Cu 13.16 (13.19).

[0041] Its infrared spectrum and X-ray diffraction single crystal structure diagram are as follows Figure 1A and Figure 1B shown.

[0042] Cell experiment of complex Z1

[0043] Adherent tumor cells in the logarithmic growth phase were selected: A-549 (lung cancer),...

Embodiment 2

[0056] Preparation of Complex Z2

[0057] 0.29g Cu(NO 3 ) 2 ·3H 2 O and 0.174g of 2,9-dimethyl-1,10-phenanthroline were sequentially added into 50ml of N,N-dimethylformamide (DMF) and stirred continuously. After reacting for 8 hours, it was filtered, the mother liquor was diffused with diethyl ether, and stood at room temperature. After several days, green blocky crystal Z2 was obtained.

[0058] The molecular formula of the Z2 compound is: {Cu[2,9-CH 3 -(1,10-Phen)](NO 3 ) 2 (DMF)}, i.e. 1 2,9-CH 3 -(1,10-Phen), 2 NO 3 And 1 DMF is coordinated with 1 Cu.

[0059] Elemental analysis (%): Calculated (exp.): C 43.54 (40.85); H 4.06 (3.36); N 19.94 (19.88); Cu 13.55 (13.87).

[0060] Its infrared spectrum and X-diffraction single crystal structure diagram are as follows Figure 2A and Figure 2B shown.

[0061] Cell experiment of complex Z2

[0062] Adherent tumor cells in the logarithmic growth phase were selected: A-549 (lung cancer), Bel-7402 (liver cancer), HCT (...

Embodiment 3

[0075] Preparation of Complex Z3

[0076] 0.29g Cu(NO 3 ) 2 ·3H 2 O and 0.174g of 2,9-dimethyl-1,10-phenanthroline were sequentially added to a mixed solution of 25mL of methanol and 25mL of acetonitrile, and the mixture was continuously stirred. After reacting for 8 hours, it was filtered, the mother liquor was diffused with diethyl ether, and allowed to stand at room temperature. After a few days, green blocky crystal Z3 was obtained.

[0077] The molecular formula of Z3 compound is: {Cu[2,9-CH 3 -(1,10-Phen)](NO 3 ) 2 (CH 3 OH)}, namely 1 2,9-CH 3 -(1,10-Phen), 2 NO 3 and 1 CH 3 OH coordinates with 1 Cu.

[0078] Elemental analysis: Calculated (exp.): C 42.11 (40.85); H 3.74 (3.36); N 13.10 (13.88); Cu 14.85 (14.67).

[0079] Its infrared spectrum and X-diffraction single crystal structure diagram are as follows Figure 3A and Figure 3B shown.

[0080] Cell experiment of complex Z3

[0081]Adherent tumor cells in the logarithmic growth phase were selected: A...

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Abstract

The invention discloses a copper complex of phenanthroline derivatives and a preparation method and application thereof, wherein the copper complex consists of 1,10-phenanthroline or single-substituted or multi-substituted derivatives thereof, acid radicals and copper ions, and can also contain organic micromolecules. The preparation method of the complex disclosed by the invention comprises the step of: reacting 1,10-phenanthroline or single-substituted or multi-substituted derivatives with a copper salt in a solvent under stirring to obtain the complex. The complex of the invention has high raw material availability and low cost, the product is separated out in the form of crystals and has high purity and high yield; besides, the complex can be stably present under a natural state, and has favorable water solubility and fat solubility; in addition, the complex of the invention exhibits superior inhibiting action on a plurality of cancer cells, such as lung cancer, gastric cancer, liver cancer, colonic adenoma, leukemia, nasopharyngeal carcinoma and the like, so both action spectrum and applicable scope of the complex are wide.

Description

technical field [0001] The present invention relates to copper complexes of phenanthroline derivatives, in particular to a class of unit substituted or multi-substituted 1,10-phenanthroline derivative copper complexes and a preparation method thereof, and the preparation of such complexes Application in drugs for the prevention and treatment of cancer and tumor diseases. Background technique [0002] Unit substituted and multi-substituted 1,10-phenanthroline derivatives not only have the properties of 1,10-phenanthroline, but also have electronegativity, electropositive effects and steric hindrance effects of substituents , chiral effect and other effects. As a planar molecule, 1,10-phenanthroline has the potential to interact with DNA in three different non-covalent ways: channel binding, intercalation binding, and intercalation binding. In addition, there are electrostatic bonds, and weak interactions such as hydrogen bonds, ionic bonds, van der Waals forces, and hydroph...

Claims

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Application Information

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IPC IPC(8): A61P35/02A61P35/00C07F1/08A61K31/555
CPCC07F1/005
Inventor 鲁晓明
Owner CAPITAL NORMAL UNIVERSITY
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