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Imidazolyl copper complex and preparation method and application thereof

A technology of imidazolyl copper and ribimidazolyl copper is applied in the field of imidazolyl copper complexes and preparation thereof, and can solve the problems of difficulty in extracting superoxide dismutase and high extraction cost

Inactive Publication Date: 2014-05-07
ANHUI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to overcome the defects of difficulty in extracting natural superoxide dismutase and high extraction cost in the prior art, and provide a kind of easy-to-prepare, low-cost and efficient hydrophilic superoxide dismutase mimetic enzyme, i.e. imidazole-based Copper complex and its preparation method and application

Method used

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  • Imidazolyl copper complex and preparation method and application thereof
  • Imidazolyl copper complex and preparation method and application thereof
  • Imidazolyl copper complex and preparation method and application thereof

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preparation example Construction

[0026] According to the present invention, the preparation method of the binuclear imidazole-based copper complex comprises: mixing N-methyl-2-hydroxymethylimidazole and copper perchlorate hexahydrate in a mixed solution of anhydrous methanol and absolute ethanol, And adjust the pH to 6.0-9.0, preferably under the condition that the pH value is 7-8, mix N-methyl-2-hydroxymethylimidazole and copper perchlorate hexahydrate for coordination reaction, filter the reaction product and crystallization.

[0027] According to the preparation method of the above-mentioned binuclear imidazole-based copper complex of the present invention, the pH of the coordination reaction has a crucial influence on the coordination reaction. When the pH is less than 6.0, the nitrogen atom on the HL will be protonated, so that it is difficult to combine with copper Ion coordination reaction, just can not obtain the imidazolium copper complex that the present invention provides; When pH is greater than 9...

Embodiment 1

[0045] Take 0.370g (1.0mmol) Cu(ClO 4 ) 2 ·6H 2 O, 0.224g (2.0mmol) N-methyl-2-hydroxymethylimidazole, 20mL mixed solvent of absolute methanol and absolute ethanol (the volume ratio of absolute methanol and absolute ethanol is 1:3), 20°C After stirring and dissolving under magnetic force, add triethylamine to adjust the pH of the solution to 8.0, and react at 80°C for 8 hours to obtain a dark blue clear solution, cool to room temperature, filter to remove insoluble matter, seal with plastic wrap, and evaporate to crystallize naturally, about 2 days later Dark blue cubic crystals A1 were precipitated with a yield of 62%.

[0046] A1 was detected, and the result of elemental analysis was C 20 h 30 Cl 2 N 8 o 12 Cu 2 : C, 30.92%; N, 14.35%; H, 4.12%, the theoretically calculated values ​​are: C, 31.10%; N, 14.51%; H, 3.91%, indicating that the results of element analysis are consistent with the results of theoretical calculation. IR (KBrdisc, cm -1 ): 3439, 3138, 2375, ...

Embodiment 2

[0048] This example adopts the method of Example 1 to prepare the imidazole-based copper complex. The difference from Example 1 is that the N-methyl-2-hydroxymethylimidazole in this example is 1.8 mmol. In this example, dark blue cubic crystal A2 was obtained with a yield of 61%.

[0049] A2 was detected, and the result of elemental analysis was C 20 h 30 Cl 2 N 8 o 12 Cu 2 : C, 30.92%; N, 14.35%; H, 4.12%, the theoretically calculated values ​​are: C, 31.10%; N, 14.51%; H, 3.91%, indicating that the results of element analysis are consistent with the results of theoretical calculation. IR (KBrdisc, cm -1 ): 3439, 3138, 2375, 2343, 2301, 1634, 1597, 1508, 1342, 1122, 1073, 752, 667, 626; single crystal diffractometer test obtained as figure 2 From the structure shown, it can be seen from infrared detection and single crystal diffraction detection that the structure of A2 is similar to the unique imidazole-bridged copper-zinc heterobinuclear structure of the SOD active ...

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Abstract

The invention discloses an imidazolyl copper complex and a preparation method and application thereof. The imidazolyl copper complex is a binuclear imidazolyl copper complex shown by formula (I) or a mononuclear imidazolyl copper complex shown by formula (II); the chemical formula of the binuclear imidazolyl copper complex is [Cu2(HL)2(L)2](ClO4)2, and the chemical formula of the mononuclear imidazolyl copper complex is [Cu(HL)2(Phen)](ClO4)2, wherein HL represents N-methyl-2-hydroxymethyl imidazole, L represents the group formed by removing H from the hydroxyl of the hydroxymethyl on the site 2 of HL, and Phen represents 1,10-o-phenanthroline. By adopting the method disclosed by the invention, the structure of the prepared imidazolyl copper complex is similar to the unique imidazole bridging copper-zinc hetero-binuclear structure of the SOD (superoxide dismutase) active center of bovine red blood cells, and then the complex can be used as a water-soluble mimic superoxide dismutase for efficiently clearing superoxide anion free radicals.

Description

technical field [0001] The invention relates to a metal-organic complex, in particular to an imidazole-based copper complex and its preparation method and application. Background technique [0002] The medical community generally believes that free radicals are an important cause of human aging and neurodegenerative diseases. Biological oxidation process provides the energy needed for life activities, and also produces superoxide anion free radicals (O 2 · - ) and other reactive oxygen species. But highly active O 2 · - It can trigger a series of free radical chain reactions and further generate more damaging hydroxyl radicals. o 2 · - It can attack the DNA in replication, cause DNA strand breaks and oxidative damage, and cause gene mutation; it can denature and cross-link proteins, make many enzymes and hormones in the body lose their biological activity, and the body's immunity and nerve reflection ability and other system activities Reduced, causing progressive ne...

Claims

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Application Information

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IPC IPC(8): C07F1/08B01J31/22A62D3/17A62D101/40
Inventor 周映华孙大亮陶骏
Owner ANHUI NORMAL UNIV
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