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Benzenesulfonamide structure-based compound of formula (I), and preparation method and application thereof

A compound and structural formula technology, applied to the compound of formula (I) based on benzenesulfonamide structure and the field of preparation and application thereof, to achieve the effects of good selectivity, less damage to cells and living bodies, and simple design strategy and synthetic route

Active Publication Date: 2019-11-05
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no fluorescent dye that can better locate the Golgi apparatus and assist in the detection of hydrogen peroxide in the Golgi apparatus.

Method used

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  • Benzenesulfonamide structure-based compound of formula (I), and preparation method and application thereof
  • Benzenesulfonamide structure-based compound of formula (I), and preparation method and application thereof
  • Benzenesulfonamide structure-based compound of formula (I), and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of Fluorescent Probes

[0042] Take the raw materials 4-bromo-1,8-naphthalenedicarboxylic anhydride (0.3g) and double pinacol boronate (0.38g) and dissolve them in 15mL of 1,4-dioxane, and then add PdCl 2 (dppf) (0.0732g) and K 2 CO3 (0.3g), refluxed at 90°C for 12h. After the reaction was complete, the solvent was removed by rotary evaporation. Then, using dichloromethane:methanol=20:1 as the eluent, the compound was purified by column chromatography to obtain a white solid intermediate product Np-Cyto (62%).

[0043] The intermediate product Np-Cyto (0.3 g) and sulfonamide (1.7 g) were taken, dissolved in 15 mL of acetic acid, and heated under reflux at 160° C. for 12 h. After the reaction was complete, the solvent was removed by rotary evaporation. Subsequently, the compound was purified by column chromatography with dichloromethane:methanol 10:1 to obtain light yellow powder Np-Golgi (10% yield).

[0044] NMR and mass spectrometry characterization:

...

Embodiment 2

[0057] Synthesis of Fluorescent Probes

[0058] Take the raw materials 4-bromo-1,8-naphthalene dicarboxylic anhydride (0.277g) and double pinacol boronate (0.35g) and dissolve them in 15mL of 1,4-dioxane, and then add PdCl 2 (dppf) (0.082g) and K 2 CO 3 (0.32g), refluxed at 90°C for 10h. After the reaction was complete, the solvent was removed by rotary evaporation. Then, using dichloromethane:methanol=20:1 as the eluent, the compound was purified by column chromatography to obtain a white solid intermediate product Np-Cyto (42%).

[0059] The intermediate product Np-Cyto (0.325 g) and sulfonamide (0.85 g) were taken, dissolved in 12 mL of acetic acid, and heated under reflux at 140° C. for 12 h. After the reaction was complete, the solvent was removed by rotary evaporation. Subsequently, the compound was purified by column chromatography with dichloromethane:methanol 10:1 to obtain light yellow powder Np-Golgi (yield 6%).

Embodiment 3

[0061] Synthesis of Fluorescent Probes

[0062] Take the raw materials 4-bromo-1,8-naphthalenedicarboxylic acid anhydride (0.28g) and double pinacol boronate (0.40g) and dissolve them in 15mL of 1,4-dioxane, and then add PdCl 2 (dppf) (0.075g) and K 2 CO 3 (0.31g), refluxed at 90°C for 12h. After the reaction was complete, the solvent was removed by rotary evaporation. Then, using dichloromethane:methanol=20:1 as the eluent, the compound was purified by column chromatography to obtain a white solid intermediate product Np-Cyto (52%).

[0063] The intermediate product Np-Cyto (0.33 g) and sulfonamide (1.2 g) were taken, dissolved in 14 mL of acetic acid, and heated under reflux at 150 °C for 12 h. After the reaction was complete, the solvent was removed by rotary evaporation. Subsequently, the compound was purified by column chromatography with dichloromethane:methanol 10:1 to obtain Np-Golgi as a light yellow powder (yield 7%).

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Abstract

The invention discloses a benzenesulfonamide structure-based compound of formula (I), and a preparation method and an application thereof. The structural formula of the compound of formula (I) is shown in the description. The compound has a superior Golgi apparatus targeting location effect when used as a fluorescent probe, has the ability to image hydrogen peroxide, and has the advantages of highsensitivity, high selectivity, and simplicity in synthesis.

Description

technical field [0001] The present invention relates to a novel detection H 2 O 2 The design strategy and synthesis method of fluorescent probes, especially those capable of targeting the Golgi apparatus to detect H 2 O 2 Synthesis of the fluorescent probe Np-Golgi. Background technique [0002] The information disclosed in this Background section is only for enhancement of understanding of the general background of the invention and should not necessarily be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art. [0003] The Golgi apparatus is a glossy membrane organelle widely present in all eukaryotes, and its main function is to process, sort, and transport proteins produced by the endoplasmic reticulum to the plasma membrane, endosomes, lysosomes or extracellular Wait. The Golgi apparatus ensures protein and lipid transport to axons and dendrites; is required in synapti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C09K11/06G01N21/64
CPCC07F5/04C09K11/06G01N21/6428G01N21/6486C09K2211/1007C09K2211/1029C09K2211/1096
Inventor 唐波王慧李平何梓旭
Owner SHANDONG NORMAL UNIV
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