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A class of naphthoquinone pyranoindole derivatives, preparation method and applications thereof

A technology of indole derivatives and naphthoquinones, applied in chemical instruments and methods, drug combinations, instruments, etc., to achieve the effects of simple synthesis, excellent fluorescence imaging performance, and good inhibitory effect

Active Publication Date: 2020-01-07
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing organic red-light aggregation-induced emission (AIE) materials mainly use tetraphenylethylene (TPE) as the AIE group, and naphthoquinonepyranoindole derivatives have not been reported as the AIE group.

Method used

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  • A class of naphthoquinone pyranoindole derivatives, preparation method and applications thereof
  • A class of naphthoquinone pyranoindole derivatives, preparation method and applications thereof
  • A class of naphthoquinone pyranoindole derivatives, preparation method and applications thereof

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Experimental program
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Effect test

Embodiment 1

[0028]

[0029] Weigh 1 mmol of 2-hydroxy-1,4-naphthoquinone, 1 mmol of substituted o-bromobenzaldehyde, 1 mmol of isonitrile, 0.2 mmol of L-proline, 0.2 mmol of cuprous iodide, and 2 mmol of potassium carbonate into a 100 mL round bottom flask In the middle, after vacuum treatment and flushing with argon, add 30 mL of dry treated toluene, heat and stir under reflux for 36 hours, cool to room temperature after the reaction is completed (TLC tracking), and spin dry the excess solvent to obtain the crude product, which is separated and purified by column chromatography ( Petroleum ether: ethyl acetate = 20:1), the target compound 5 was obtained.

[0030] Take compound 5a as an example:

[0031] Weigh 1 mmol of 2-hydroxy-1,4-naphthoquinone, 1 mmol of o-bromobenzaldehyde, 1 mmol of cyclohexylisonitrile, 0.2 mmol of L-proline, 0.2 mmol of cuprous iodide, and 2 mmol of potassium carbonate into a 100 mL round bottom In the flask, after vacuum treatment and flushing with argon, ad...

Embodiment 2

[0126] Using ethyl acetate as solvent, the compound 5 was formulated into 1×10 -5 mol L -1 The dilute solution of the test UV absorption spectrum is shown in Figure 1. Depend on figure 1It can be seen that the ultraviolet absorption wavelength of compound 5 is in the range of 495-525nm, entering the visible light region, indicating that there is a relatively long conjugated system in the molecule of 5, and the charge transfer is very smooth and easy. The absorption peaks appear in the visible light region, indicating that the series of compounds have less damage to living cells, and have the potential to be further prepared into biological probes and imaging reagents.

[0127] The photos of the solution and solid state of compound 5 under the irradiation of 365nm ultraviolet lamp are as follows: figure 2 As shown, in each photo, the left side is the solid of the compound, and the right side is the solution of the compound, obtained by dissolving in chloroform as a solvent....

Embodiment 3

[0131] The antitumor activity of embodiment 3 products

[0132] MTT method was used to preliminarily test the effect of compound 5 on human triple-negative breast cancer cells (MDA-MB-231), human liver cancer cells (HepG-2), human lung cancer cells (A549), human liver immortalized cells (THLE) and human Cytotoxicity of bronchial epithelial cells (HBE), test results show that only 5b has inhibitory effect on MDA-MB-231 and A549, and is also toxic to normal cells. If it is to be further developed into an anti-tumor drug, the structure must be modified .

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Abstract

The invention relates to a class of naphthoquinone pyranoindole derivatives, which have a structural general formula represented by the following formula 5, and is prepared by carrying out heating refluxing on substituted 4-hydroxycoumarin, isonitrile and o-bromobenzaldehyde in anhydrous toluene in the presence of K2CO3 under the catalysis of proline-CuI in argon gas. According to the invention, the naphthoquinone pyranoindole derivative has a fluorescence emission peak at 620-650nm and a Stokes shift of 115-125nm, emits red light, has solid-state fluorescence and aggregation-state induced fluorescence effects, can perform fluorescence imagingon human lung cancer (A549) cells, has inhibition effect on multiple triple-negative breast cancer (MDA-MB-231), breast cancer (MCF-7) or human lungcancer (A549) cell strains, and has application potential in the fields of preparation of anti-lung cancer and anti-breast cancer specific drugs and novel red fluorescence imaging probes.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a class of naphthoquinonepyranoindole derivatives and their preparation methods and applications. Background technique [0002] Red light materials, especially near-infrared materials, are in high demand in biological imaging. This is because organisms in the near-infrared and far-infrared regions have the advantages of strong penetrating ability, low excitation energy, small background fluorescence interference, and less absorption and autofluorescence, which can improve the signal-to-noise ratio and sensitivity of imaging. In addition, due to its low energy, near-infrared light is less harmful to organisms; and due to its longer wavelength, it has a strong ability to penetrate tissues. Therefore, obtaining organic red light compounds with novel structures has important theoretical significance and application value in many fields. [0003] Red-light aggregation-in...

Claims

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Application Information

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IPC IPC(8): C07D491/048A61P35/00C09K11/06G01N21/64
CPCC07D491/048A61P35/00C09K11/06G01N21/6486C09K2211/1033
Inventor 吴翚张珑严苑睿宛瑜
Owner XUZHOU NORMAL UNIVERSITY
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