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Novel Tr*ger's Base-imidazole derivatives and preparation method and application thereof

An imidazole derivative, a new type of technology, applied in chemical instruments and methods, drug combinations, organic chemistry, etc., to achieve the effects of convenient post-processing, mild conditions, and good inhibitory effect

Active Publication Date: 2020-08-07
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, a variety of fluorophores have been used in luminescent materials, such as coumarin, chromone, julolide, naphthalene ring, acylhydrazone, rhodamine, 1,2-dihydroxyanthraquinone, 8-hydroxy quinoline, morin, etc., but there is no report on the use of phenanthroimidazole derivatives for luminescent materials

Method used

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  • Novel Tr*ger's Base-imidazole derivatives and preparation method and application thereof
  • Novel Tr*ger's Base-imidazole derivatives and preparation method and application thereof
  • Novel Tr*ger's Base-imidazole derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1 new type Synthesis of Base-imidazole derivatives

[0033] 1. Synthesis of Intermediate 1

[0034] Weigh 10.32g (60mmol) of p-bromoaniline and paraformaldehyde (n=3,150mmol) into a 250mL round-bottomed flask and cool to minus 15°C, slowly add 120mL of trifluoroacetic acid dropwise through a constant pressure dropping funnel. The reaction system was moved to room temperature for seven days, quenched with ice water, adjusted to neutral pH with ammonia water, extracted with dichloromethane, and the organic phase was extracted with saturated brine, dried over anhydrous sodium sulfate, separated and purified by column chromatography (V 石油醚 :V 乙酸乙酯 =5:1), and finally recrystallized with acetone, dried, weighed, and collected to obtain intermediate 1.

[0035] 2. Synthesis of Intermediate 3

[0036] Weigh 5 mmol of the solid compound 3 into a 100 mL round-bottomed flask, add 20 mL of dry-treated tetrahydrofuran, cool the system to minus 78 °C under anhydrous a...

Embodiment 2

[0299] Example 2 The aggregation-inducing effect of each product of the present invention

[0300] In this example, compounds c4 and a3 are taken as examples to illustrate the aggregation-inducing effect of the products. with tetrahydrofuran and distilled water according to V DTHF :V H2O 10:0, 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, 1:9 are used as solvents in different ratios, and the compound is formulated as 1 ×10 -6 mol L -1 solution to test the product in different THF-H 2 The relationship between the fluorescence intensity and the water content in the solvent with O ratio, the results show that the novel The Base-imidazole derivatives emit blue light, have obvious aggregation-induced luminescence and solid-state luminescence, and have application potential in the preparation of new blue solid-state luminescent materials and aggregation-induced blue light materials.

Embodiment 3

[0301] Embodiment 3 thermogravimetric analysis

[0302] The thermal stability of the compound was tested by a thermogravimetric analyzer, the heating rate was 10° C. / min, and the test range was 0-400° C. under nitrogen. The results show that the temperature for compound a4 to lose 5% of its weight is 180°C, and when the temperature reaches 200°C, the compound begins to decompose, and the temperature for compounds c2, a3, and c7 to lose 5% of their weight is about 200°C, and it does not start until the temperature reaches 350°C break down. The longer the conjugated system of the molecule, the higher the decomposition temperature, which is in line with the general rule. The results show that this type of compound has good thermal stability, meets the basic requirements of device materials, and has certain application potential.

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Abstract

The structural general formula of the novel Base-imidazole derivative is shown as any one of the following formulas, and the novel Base-imidazole derivative is prepared from p-bromoaniline, paraformaldehyde, n-butyllithium, phenanthrenequinone / biphenyl formyl / acenaphthenequinone and substituted aniline through cyclization and coupling reaction. The novel Base-imidazole derivative provided by the invention emits blue light, has obvious aggregation-induced emission and solid-state emission, has good thermal stability, meets the basic requirements of device materials, and has certain applicationpotential. Part of the novel Base-imidazole derivatives have a good inhibition effect on one or two of triple-negative breast cancer cells and liver cancer cells, and have low toxicity to normal cells; part of the novel Base-imidazole derivatives can inhibit one or more of non-small cell lung cancer cells, triple negative breast cancer cells and lung cancer cells to a certain extent.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a class of novel Base-imidazole derivatives and their preparation methods and applications. Background technique [0002] The main parts in the molecular structure of fluorescent probes are signal unit (chromophore), spacer unit (chemical bridge) and binding unit (acceptor). The structure also contains a variety of auxiliary chromophores and functional groups, such as amino, carboxylic acid, Carbonyl, hydroxyl, etc. These functional groups can change the ability of the chromophore to absorb light. By changing these three key fragments, the host-guest interaction or selective chemical reaction can be changed, thereby changing the fluorescent properties of the system to achieve the purpose of designing specialized probes for specific targets. [0003] Imidazole is a five-membered planar aromatic ring compound. Its unique electron delocalization and resonance structure make it h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08C07D519/00C09K11/06A61P35/00A61P31/10
CPCC07D487/08C07D519/00C09K11/06A61P35/00A61P31/10C09K2211/1044C09K2211/1074C09K2211/1007
Inventor 孙雅文苑睿窦鹏飞宋仅星宛瑜吴翚
Owner XUZHOU NORMAL UNIVERSITY
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