Compound of formula (i) based on benzenesulfonamide structure and its preparation method and application

A technology of compound and structural formula, applied in the field of compound of formula (I) based on benzenesulfonamide structure and its preparation and application, to achieve the effect of less damage to cells and living organisms, simple design strategy and synthetic route, and high response multiple

Active Publication Date: 2022-04-15
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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  • Compound of formula (i) based on benzenesulfonamide structure and its preparation method and application
  • Compound of formula (i) based on benzenesulfonamide structure and its preparation method and application
  • Compound of formula (i) based on benzenesulfonamide structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of fluorescent probes

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

[0043] The intermediate product Np-Cyto (0.3g) and sulfonamide (1.7g) were dissolved in 15mL of acetic acid, and heated at reflux at 160°C for 12h. 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:

[0045] 1 H NMR (400MHz, CDCl 3 )δ9.20(d,...

Embodiment 2

[0057] Synthesis of fluorescent probes

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

[0059] Take the intermediate product Np-Cyto (0.325g) and sulfonamide (0.85g), dissolve it in 12mL of acetic acid, and heat at reflux at 140°C for 12h. 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] Dissolve the raw material 4-bromo-1,8-naphthalic anhydride (0.28g) and bis-pinacol borate (0.40g) in 15mL of 1,4-dioxane, and then add PdCl 2 (dppf)(0.075g) and K 2 CO 3 (0.31g), reflux at 90°C for 12h. After the reaction was complete, the solvent was removed by rotary evaporation. Subsequently, the compound was purified by column chromatography using dichloromethane:methanol=20:1 as the eluent to obtain the white solid intermediate product Np-Cyto (52%).

[0063] The intermediate product Np-Cyto (0.33g) and sulfonamide (1.2g) were dissolved in 14mL of acetic acid and heated under reflux at 150°C for 12h. 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 7%).

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Abstract

The invention discloses a compound of the formula (I) based on the structure of benzenesulfonamide and its preparation method and application. The compound of the formula (I) has the structural formula: the compound acts as a fluorescent probe and exhibits excellent Golgi targeting positioning effect, and can image hydrogen peroxide, and has the advantages of high sensitivity, high selectivity and simple synthesis.

Description

technical field [0001] The invention relates to a new type of target-positioning Golgi apparatus based on the structure of benzenesulfonamide to detect 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 intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled 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. Golgi apparatus ensures p...

Claims

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Application Information

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Patent Type & Authority Patents(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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