A kind of tröger's base-Schiff base derivative and its preparation method and application

A technology of derivatives and anticancer drugs, applied in the field of base-Schiff base derivatives and their preparation, to achieve the effects of low toxicity, readily available raw materials, and mild conditions

Active Publication Date: 2022-04-26
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, a variety of fluorophores have been used to detect metal ions, 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 benzimidazoloquinazoline derivatives for metal ion recognition and detection

Method used

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  • A kind of tröger's base-Schiff base derivative and its preparation method and application
  • A kind of tröger's base-Schiff base derivative and its preparation method and application
  • A kind of tröger's base-Schiff base derivative and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1ba

[0044] Example 1 Synthesis of base-Schiff base derivatives 12 and 13

[0045] 1. Synthesis of Intermediate 3

[0046] Weigh 10.32g (60mmol) of p-bromoaniline and 4.5g (150mmol, n=3) of paraformaldehyde into a 250mL round bottom flask and cool to minus 15°C, slowly add 120mL of trifluoroacetic acid dropwise through a constant pressure dropping funnel, After dropping, move the reaction system to room temperature for 7 days, quench with ice water, adjust the pH to neutral with ammonia water, extract with dichloromethane, extract the organic phase with saturated saline, dry over anhydrous sodium sulfate, and perform column chromatography Separation and purification (petroleum ether: ethyl acetate = 5:1), and finally recrystallization with acetone, drying, weighing, and collection to obtain intermediate 3.

[0047] 2. Synthesis of Intermediate 4a

[0048]Weigh 5mmol of the solid compound 3 into a 100mL round bottom flask, add 20mL of dry THF, cool the system to minus 78°C under...

Embodiment 2

[0300] Example 2 The aggregation-inducing effect of each product of the present invention

[0301] In this example, compounds 12c and 12o were taken as examples to illustrate the aggregation-inducing effect of the products. with tetrahydrofuran and distilled water according to V DTHF :V H2O Different ratios of 10:0, 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, 1:9 are used as solvents, compound 12 into 1×10 -6 mol L -1 solution to test the product in different THF-H 2 The relationship between fluorescence intensity and water content in the solvent with O ratio, the test results are as follows figure 1 shown. from figure 1 It can be seen that the present invention The base-Schiff base derivative has excellent luminescence performance, is blue luminescence, has obvious aggregation-induced luminescence and solid-state luminescence, and has application potential in the preparation of new blue solid-state luminescence materials and aggregation-induced blue luminescence materials....

Embodiment 3

[0302] Embodiment 3 metal ion detection

[0303] The metal ion recognition experiment results of each compound are shown in Table 2 below

[0304] Table 2 The fluorescence intensity of the product for the recognition of 7 metal ions

[0305]

[0306] The sign "-" indicates the decrease of relative fluorescence intensity after adding metal ions, and no sign indicates the increase of relative fluorescence intensity after adding metal ions.

[0307] As can be seen from Table 2, this type of compound has a good effect on Sn 4+ , Fe 3+ 、Al 3+ All have good response, and the relative fluorescence intensity has varying degrees of change. Among them, compound 12d had the most obvious and specific fluorescence intensity after adding metal ions.

[0308] The compound 12d and its intermediate 8 were compared and tested under the same conditions, and the test results are shown in Table 3 below.

[0309] Spectral data of table 3 compound 12d and its intermediate after adding metal...

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Abstract

A class of base-Schiff base derivatives, whose general structural formula is shown in the following formula [I], which is formed by condensation of raw materials such as p-bromoaniline, paraformaldehyde, n-butyllithium, p-aminobenzoic acid, substituted o-phenylenediamine, etc. The reaction is made. The fluorescence of base-Schiff base derivatives of the present invention is blue luminescence, has obvious aggregation-induced luminescence and solid-state luminescence, and some compounds are sensitive to Al 3+ With recognition ability, the two compounds have a good inhibitory effect on one or both of triple-negative breast cancer cells and liver cancer cells, and are less toxic to normal cells; the three compounds are effective against non-small cell lung cancer cells, triple-negative breast cancer cells One or more of the three types of cells and lung cancer cells have a certain degree of inhibitory effect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a class of Base-Schiff base 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 can contain various color aids 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 fluorescent properties of the system can be changed by changing the host-guest interaction or selective chemical reaction, so as to achieve the purpose of designing probes specifically targeting specific targets. [0003] A Schiff base refers to an organic compound containing an imine or imine group in its structure, and is generally formed by condensa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/08C09K11/06A61P35/00A61P31/00G01N21/64
CPCC07D487/08C09K11/06A61P35/00A61P31/00G01N21/643C09K2211/1044C09K2211/1033C09K2211/1037
Inventor 周杭张珑严苑睿宛瑜吴翚
Owner XUZHOU NORMAL UNIVERSITY
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