Trinuclear Schiff base metal complex and its preparation method and use

A tri-nuclear Schiff and Schiff base technology, applied to iron group organic compounds without C-metal bonds, 1/11 group organic compounds without C-metal bonds, and 2/12 group organic compounds without C-metal bonds Compounds and other directions can solve the problems of limited application and no biological activity research, and achieve the effects of inhibiting angiogenesis, excellent anti-reactive oxygen species performance, and good redox activity

Active Publication Date: 2022-01-11
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Salen-type complexes are compounds developed on the basis of tetradentate ligand Schiff bases, but the reported salen-type complexes only have catalytic properties, fluorescence imaging, etc., and no specific research on biological activity , thus limiting their application in the field of medicine

Method used

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  • Trinuclear Schiff base metal complex and its preparation method and use
  • Trinuclear Schiff base metal complex and its preparation method and use
  • Trinuclear Schiff base metal complex and its preparation method and use

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preparation example Construction

[0065] The present invention also provides a preparation method of the above-mentioned trinuclear Schiff base metal organic complex, the preparation method comprising the following steps:

[0066] 1) under an inert atmosphere, under catalytic conditions, anisole and ethyl chloroformate react in a first organic solvent to obtain a first intermediate product;

[0067] 2) reacting the first intermediate product with p-toluenesulfonic acid in a second organic solvent to obtain a second intermediate product;

[0068] 3) under catalytic conditions, reacting the second intermediate product with N,N-dimethylformamide in a third organic solvent to obtain a third intermediate product;

[0069] 4) In the fourth organic solvent, remove the methyl group on the methoxy group of the third intermediate product to obtain the fourth intermediate product;

[0070] 5) Condensing the fourth intermediate product with the diamine in the fifth organic solvent, and then performing ligand replacement ...

Embodiment 1

[0130] Synthesis of complex 1:

[0131]

[0132] Mix anisole and ethyl chloroformate in anhydrous ether, and react under nitrogen atmosphere at 0-10°C to obtain the first intermediate product; the first intermediate product is mixed with p-toluene at room temperature (0°C-30°C) Sulfonic acid is reacted in acetonitrile and tetrahydrofuran mixed solvent to obtain the second intermediate product; the second intermediate product is reacted with N,N-dimethylformamide in anhydrous ether to obtain the third intermediate product; the third intermediate product and three Boron bromide was reacted in dichloromethane to obtain the fourth intermediate product; the fourth intermediate product was reacted with o-phenylenediamine, then reacted with manganese acetate, and the ligand was exchanged with LiCl solution to obtain complex 1. ESI HRMSm / z=1197.03356 calcd for [C 62 h 38 Cl 2 mn 3 N 6 o 6 ] + =1197.04. Elemental analysis C, 60.59; H, 3.35; N, 6.76.

Embodiment 2

[0134] Synthesis of complex 2:

[0135]

[0136] Mix anisole and ethyl chloroformate in anhydrous ether, and react at room temperature under nitrogen atmosphere to obtain the first intermediate product; the first intermediate product is reacted with p-toluenesulfonic acid in acetonitrile and tetrahydrofuran mixed solvent at room temperature , to obtain the second intermediate product; the second intermediate product reacts with N,N-dimethylformamide in anhydrous ether to obtain the third intermediate product; the third intermediate product reacts with boron tribromide in dichloromethane to obtain The fourth intermediate product; the fourth intermediate product is reacted with 1,2-cyclohexanediamine, then reacted with manganese acetate, and the ligand is exchanged with LiCl solution to obtain complex 2. ESI HRMS m / z=1215.17518 calcd for [C 62 h 56 Cl 2 mn 3 N 6 o 6 ] + =1215.18. Elemental analysis C, 59.39; H, 4.69; N, 6.66.

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Abstract

The invention provides a trinuclear Schiff base metal organic complex comprising a trinuclear Schiff base ligand, a metal ion and an axial ligand, and a preparation method and application thereof. The complex has excellent performance against active oxygen species and superior Biocompatibility, capable of repairing diseases related to reactive oxygen species, has a prospect of biomedical application targeting reactive oxygen species.

Description

technical field [0001] The invention relates to the field of metal medicines, in particular to a trinuclear Schiff base metal organic complex with redox activity and capable of removing reactive oxygen species, a preparation method and therapeutic application thereof. Background technique [0002] Metal Schiff base complexes refer to metal complexes formed by the coordination of metal elements and Schiff bases. Display, agriculture, and photochromic fields all play an important role. [0003] Metal Schiff base complexes are usually used in catalytic reactions, such as epoxidation of alkenes, oxidation of hydrocarbons, enzymatic catalysis, etc.; they can also be used as bioactive agents, such as anticancer and antitumor therapeutic drugs. [0004] Salen-type complexes are compounds developed on the basis of the tetradentate ligand Schiff base, but the reported salen-type complexes only have catalytic properties, fluorescence imaging, etc., and no specific research on biologi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00C07F15/02C07F5/06C07F3/06C07F1/08C07F15/00A61P39/06A61P35/00A61P27/02A61P9/10A61P29/00A61P25/00A61K31/555A61K31/439
CPCC07F13/005C07F15/025C07F5/069C07F3/003C07F1/005C07F15/0093A61P39/06A61P35/00A61P27/02A61P9/10A61P29/00A61P25/00
Inventor 张俊龙宁莹莹林恒宇王炳武康磊霍焱
Owner PEKING UNIV
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