A new class of tröger's Base-imidazole derivatives and their preparation methods and applications

A technology of imidazole derivatives and products is applied in the field of novel Base-imidazole derivatives and their preparation, and achieves the effects of good inhibition, good thermal stability and convenient post-processing

Active Publication Date: 2022-07-19
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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  • A new class of tröger's Base-imidazole derivatives and their preparation methods and applications
  • A new class of tröger's Base-imidazole derivatives and their preparation methods and applications
  • A new class of tröger's Base-imidazole derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Novel 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, after dropping The reaction system was moved to room temperature and reacted for seven days, quenched with ice water, adjusted to neutral pH with ammonia water, extracted with dichloromethane, the organic phase was then extracted with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography (V 石油醚 : V 乙酸乙酯 =5:1), finally recrystallized with acetone, dried, weighed and collected to obtain intermediate 1.

[0035] 2. Synthesis of Intermediate 3

[0036] Weigh 5 mmol of solid compound 1 into a 100 mL round-bottomed flask, add 20 mL of dried tetrahydrofuran, cool the system to minus 78°C under...

Embodiment 2

[0297] Example 2 Aggregation-inducing effect of each product of the present invention

[0298] In this example, compounds c4 and a3 are used as examples to illustrate the aggregation-inducing effect of the products. with tetrahydrofuran and distilled water according to V DTHF :V H2O For different ratios of 10:0, 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, 1:9 as solvents, the compounds were formulated into 1 ×10 -6 mol·L -1 solutions to test products in different THF-H 2 The relationship between the fluorescence intensity and the water content in the solvent with O ratio shows that the new Base-imidazole derivatives are blue light-emitting, have obvious aggregation-induced light-emitting and solid-state light-emitting, and have application potential in the preparation of new blue solid-state light-emitting materials and aggregation-induced blue light materials.

Embodiment 3

[0299] Example 3 Thermogravimetric analysis

[0300] The thermal stability of these compounds was tested by a thermogravimetric analyzer with a heating rate of 10°C / min and a test range of 0-400°C under nitrogen. The results show that the temperature at which the compound a4 loses 5% of its weight is 180°C, and when the temperature reaches 200°C, the compound begins to decompose; the temperature at which the compound c2, a3, and c7 loses 5% weight is about 200°C, and 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 conforms to the general rule. The results show that the compounds have good thermal stability, meet the basic requirements of device materials, and have certain application potential.

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Abstract

A new type of Base-imidazole derivatives, the general structural formula of which is shown in any of the following formulas, which is composed of p-bromoaniline, paraformaldehyde, n-butyllithium, phenanthrenequinone / bibenzoyl / acenaphthylquinone, substituted aniline through the formation of Ring, coupling reaction obtained. The novel Base-imidazole derivative of the present invention is blue light-emitting, has obvious aggregation-induced light-emitting and solid-state light-emitting, has good thermal stability, meets the basic requirements of device materials, and has certain application potential. Some of the new Base-imidazole derivatives have good inhibitory effects on one or both of triple-negative breast cancer and liver cancer cells, and are less toxic to normal cells; some of the new Base-imidazole derivatives are effective against non-small cell lung cancer, One or more of the three cancer cells of triple-negative breast cancer and lung cancer are inhibited to some extent.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a new type of Base-imidazole derivatives and preparation method and application thereof. Background technique [0002] The main parts of the molecular structure of fluorescent probes are signal unit (chromophore), spacer unit (chemical bridge) and binding unit (acceptor). 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 fluorescence properties of the system, so as 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 have both the electron withdrawing property of pyridine and the electron donating property of pyrrole,...

Claims

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Application Information

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Patent Type & Authority Patents(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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