Copper complex of phenanthroline derivative as well as preparation method and application of copper complex

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 good water solubility and fat solubility, high purity, and wide application range wide range of effects

Inactive Publication Date: 2017-03-29
CAPITAL NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 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 derivative as well as preparation method and application of copper complex
  • Copper complex of phenanthroline derivative as well as preparation method and application of copper complex
  • Copper complex of phenanthroline derivative as well as preparation method and application of copper complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of complex Z1

[0040] 0.29g Cu(NO 3 ) 2 ·3H 2 O and 0.174g 2,9-dimethyl-1,10-phenanthroline were sequentially added to 10ml N,N-dimethylacetamide (DMA), 50ml anhydrous methanol, and kept stirring. 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.

[0041] 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 NOs 3 and 1 DMA coordinated to 1 Cu.

[0042] Elemental analysis (%): Calculated (exp.): C 44.77 (44.66); H 4.35 (3.30); N 14.51 (14.46); Cu 13.16 (13.19).

[0043] Its infrared spectrum and X-ray diffraction single crystal structure diagram are as follows Figure 1A and Figure 1B shown.

[0044] Cell experiment of complex Z1

[0045] Adherent tumor cells in the logarithmic growth phase were selected: A-549 (lung cancer), Bel-7402 (l...

Embodiment 2

[0058] Preparation of Complex Z2

[0059] 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 kept stirring. 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.

[0060] The molecular formula of 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 NOs 3 And 1 DMF is coordinated with 1 Cu.

[0061] Elemental analysis (%): Calculated (exp.): C 43.54 (40.85); H 4.06 (3.36); N 19.94 (19.88); Cu 13.55 (13.87).

[0062] Its infrared spectrum and X-diffraction single crystal structure diagram are as follows Figure 2A and Figure 2B shown.

[0063] Cell experiment of complex Z2

[0064] Adherent tumor cells in the logarithmic growth phase were selected: A-549 (lung cancer), Bel-7402 (liver cancer), HCT (colon ade...

Embodiment 3

[0077] Preparation of Complex Z3

[0078] 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.

[0079] The molecular formula of Z3 compound is: {Cu[2,9-CH 3 -(1,10-Phen)](NO 3 ) 2 (CH 3 OH)}, i.e. 1 2,9-CH 3 -(1,10-Phen), 2 NOs 3 and 1 CH 3 OH coordinates with 1 Cu.

[0080] Elemental analysis: Calculated (exp.): C 42.11 (40.85); H 3.74 (3.36); N 13.10 (13.88); Cu 14.85 (14.67).

[0081] Its infrared spectrum and X-diffraction single crystal structure diagram are as follows Figure 3A and Figure 3B shown.

[0082] Cell experiment of complex Z3

[0083]Adherent tumor cells in the logarithmic growth phase were selected: A-...

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Abstract

The invention discloses a copper complex of a phenanthroline derivative, a preparation method and application of the copper complex. The copper complex of the phenanthroline derivative comprises one or multiple substitutive derivatives of 1,10-phenanthroline, acid radicals and / or small organic molecules (comprising solvent molecules) and copper ions. The preparation method of the complex comprises the steps of stirring the one or multiple substitutive derivatives of 1,10-phenanthroline and copper salt in a solvent and reacting to obtain the complex. The copper complex has the beneficial effects that the raw materials for synthesizing the complex are easily available and low in cost, and the product is separated out in a crystal manner and has high purity and high yield; the copper complex can exist stably in a natural state and has good water solubility and lipid solubility; in addition, the copper complex has an excellent inhibiting effect on multiple cancer cells such as lung cancer cells, gastric cancer cells, liver cancer cells, colonic adenocarcinoma cells, leukemia cells, nasopharynx cancer cells and the like, a wide action spectrum and a wide application range.

Description

[0001] Case Description [0002] This case is a divisional application of a Chinese invention patent application with an application date of February 5, 2010, an application number of 2010191114033.8, and an invention title of "copper complexes of o-phenanthroline derivatives and their preparation methods and applications". technical field [0003] 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 [0004] Unit substituted and multiple 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08A61K31/555A61P35/00A61P35/02
CPCC07F1/005
Inventor 鲁晓明
Owner CAPITAL NORMAL UNIVERSITY
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