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2-(1H-tetrazole-1-methyl)-1H-imidazole-4, 5-dicarboxylic acid cobalt complex and preparation method and application thereof

A cobalt complex, C-115 technology, applied in the field of coordination chemistry, can solve the problems of increasing the structure and performance of the steric hindrance effect, achieve the effect of increasing the inhibition rate, mild reaction conditions, and improving fat solubility

Active Publication Date: 2020-06-12
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The introduction of the 2-position substituent does not change the coordination point of imidazole dicarboxylic acid, but it can increase the steric hindrance effect and thus affect the structure and properties of the resulting complex
[0005] Coordinate the biologically active 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid ligand with cobalt ions to obtain a complex, and study the relationship between the complex and bovine serum white The mechanism of protein (BSA) interaction has not been reported

Method used

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  • 2-(1H-tetrazole-1-methyl)-1H-imidazole-4, 5-dicarboxylic acid cobalt complex and preparation method and application thereof
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  • 2-(1H-tetrazole-1-methyl)-1H-imidazole-4, 5-dicarboxylic acid cobalt complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: The preparation method of 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid

[0044] (1) 2-(1H-tetrazolium-1-methyl)-1H-benzimidazole (bimt)

[0045] Put 40mmol o-phenylenediamine and 44mmol tetrazoleacetic acid in a round bottom flask, add 50ml of 4mol / L hydrochloric acid, stir to dissolve, heat up to reflux, react for 4h, the solution is brown, cool to room temperature, and add the reaction solution to 100ml of ice water, mix well, add saturated sodium hydroxide solution to adjust pH = 8.0, a large amount of precipitates precipitate out, filter with suction, wash with distilled water until neutral, and dry to obtain the crude product, which is recrystallized with distilled water to obtain long silver-gray needles 5.4614g of crystals, namely 2-(1H-tetrazolium-1-methyl)-1H-benzimidazole, yield: 68.20%;

[0046] (2) 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid (H 6 tmidc)

[0047] Add 15ml of mass fraction 98% concentrated sul...

Embodiment 2

[0048] Example 2: Structural characterization of 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid

[0049] Utilize Bruker ABANCEⅢ500MHz nuclear magnetic resonance instrument, take tetramethylsilane as standard substance, the 2-(1H-tetrazolium-1-methyl)-1H-benzimidazole (bimt) that embodiment 1 obtains and 2-(1H -tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid (H 6 tmidc) were dissolved with MeOD and deuterated DMSO respectively, and analyzed by hydrogen spectrum. The test results are:

[0050] figure 1 It is the nuclear magnetic resonance spectrum of 2-(1H-tetrazolium-1-methyl)-1H-benzimidazole (bimt), 1 HNMR (MeOD, 500MHz), δ=9.37(s, 1H, Tetra-H), attributed to hydrogen on tetrazole, δ=7.58(m, 2H, Ar-H), δ=7.27-7.29(m, 2H, Ar-H), δ=6.02(t, 2H, CH 2 ).

[0051] figure 2 For 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid (H 6 tmidc) NMR spectrum, 1 HNMR (DMSO, 500MHz), δ=9.50(s, 1H, Tetra-H), attributed to the hydrogen on the tetr...

Embodiment 3

[0052] Example 3: Preparation method of 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid cobalt complex

[0053] (1) 0.05mmol of 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylic acid was dissolved in 2ml of water to prepare a ligand solution;

[0054] 0.1mmol CoSO 4 ·7H 2 O dissolved in 4ml of water to make CoSO 4 solution;

[0055] (2) CoSO 4 Add the solution dropwise to the ligand solution, then add 2 drops of DMF (dimethylformamide), mix evenly, place in a reaction kettle with a polytetrafluoroethylene liner, and react in an oven at 120°C for 72h. After the reaction Cool to room temperature at a rate of 5°C / h to obtain blocky pink transparent crystals, namely 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylate cobalt complex , the yield was 78%.

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Abstract

The invention discloses a 2-(1H-tetrazole-1-methyl)-1H-imidazole-4, 5-dicarboxylic acid cobalt complex and a preparation method and application thereof, and the technical scheme is as follows: 2-(1H-tetrazole-1-methyl)-1H-imidazole-4, 5-dicarboxylic acid is used as a ligand to construct a coordination polymer with metal ion cobalt to obtain a brand-new 2-(1H-tetrazole-1-methyl)-imidazole-4, 5-dicarboxylic acid cobalt complex. The complex is simple in synthesis method, mild in reaction condition and high in purity. Experimental results show that the complex has strong binding capacity with BSA,and the complex has an inhibition effect on proliferation of esophageal cancer cells Eca109 and is similar to cis-platinum and has an inhibition rate of increasing the inhibition rate of the complexon Eca109 after 48 hours. Therefore, the complex is expected to be developed into a novel complex antitumor drug for treating esophageal cancer caused by Eca109 cells.

Description

technical field [0001] The invention relates to a 2-(1H-tetrazolium-1-methyl)-1H-imidazole-4,5-dicarboxylate cobalt complex and a preparation method and application thereof, belonging to the field of coordination chemistry. Background technique [0002] As a multi-dentate chelating ligand, imidazole dicarboxylic acid contains heterocyclic imidazole ring and carboxyl group at the same time, has different functional coordination atoms N and O, and can coordinate with various metals to form complexes. In addition, the structure of the target product can also be regulated by adjusting the 2-substituent of imidazole dicarboxylic acid. The introduction of the 2-position substituent does not change the coordination point of imidazole dicarboxylic acid, but it can increase the steric hindrance effect and affect the structure and performance of the complex. Studies have shown that imidazole derivatives have various physiological functions such as antibacterial and antiviral, and tet...

Claims

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Application Information

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IPC IPC(8): C08G83/00A61P35/00
CPCA61P35/00C08G83/008
Inventor 郭晓玉李雪菊刘艳菊张军娣王笑阳李盈盈
Owner HENAN UNIV OF CHINESE MEDICINE