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Compound represented by formula (I), and preparation method and application thereof

A compound and reaction technology, applied in the field of formula compounds and their preparation, can solve the problems of complex synthesis, high price, technology monopoly, etc., and achieve the effect of cheap and easy-to-obtain raw materials and simple synthetic routes

Active Publication Date: 2019-10-29
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, among the various commercial subcellular organelle localization dyes on the market, most of them are imported commercial dyes, and the price of such commercial dyes is high due to the complex synthesis and technical monopoly

Method used

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  • Compound represented by formula (I), and preparation method and application thereof
  • Compound represented by formula (I), and preparation method and application thereof
  • Compound represented by formula (I), and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of dye Rd-Golgi:

[0036] The raw material Rhodamine B (0.48g) was dissolved in 2.5mL of phosphorus oxychloride solution and refluxed at 80°C for 12h. After the reaction was completed, excess phosphorus oxychloride was removed by rotary evaporation. Then dissolve the product of the above step with 10mL acetonitrile, and add sulfonamide (0.4305g) and 324μL triethylamine as an acid-binding agent, react at room temperature for 12h, need to use triethylamine as an acid-binding agent, after the acid chloride and sulfonamide react during the reaction Hydrogen bromide will be generated, adding triethylamine can neutralize hydrogen bromide and move the chemical reaction equilibrium forward. Then using dichloromethane:methanol=20:1 as eluent, the compound was purified by column chromatography to obtain a pink solid named as Rd-Golgi (the yield was 21%).

[0037] NMR and mass spectrometry characterization:

[0038] 1 H NMR (400MHz, CDCl 3 )δ=7.91(dd,J=6.2,1.7,1H),7...

Embodiment 2

[0042]Synthesis of dye Rd-Golgi:

[0043] The raw material rhodamine B (0.51g) was dissolved in 2.5mL of thionyl chloride solution and refluxed at 85°C for 14h. After the reaction was completed, excess phosphorus oxychloride was removed by rotary evaporation. Then the product of the above step was dissolved with 10 mL of acetonitrile, and sulfonamide (0.4305 g) and 324 μm triethylamine were added as acid-binding agents, and reacted at room temperature for 12 h. Then, dichloromethane:methanol=20:1 was used as eluent, and the compound was purified by column chromatography to obtain a pink solid.

Embodiment 3

[0045] Synthesis of dye Rd-Golgi:

[0046] The raw material Rhodamine B (0.45g) was dissolved in 2.5mL of phosphorus oxychloride solution and refluxed at 78°C for 12h. After the reaction was completed, excess phosphorus oxychloride was removed by rotary evaporation. Then the product of the above step was dissolved in 10 mL of acetonitrile, and sulfonamide (0.4214 g) and 324 μL of triethylamine were added as an acid-binding agent, and reacted at room temperature for 12 h. Then, dichloromethane:methanol=20:1 was used as eluent, and the compound was purified by column chromatography to obtain a pink solid.

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PUM

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Abstract

The invention discloses a compound represented by a formula (I), and a preparation method and application thereof. The compound represented by formula (I) has the following structural formula. The compound has an excellent Golgi apparatus targeting positioning effect when being used as a dye.

Description

technical field [0001] The invention belongs to the technical field of Golgi apparatus dyes, and specifically relates to a compound of formula (I) and its preparation method and application. As a dye, the compound can target the Golgi apparatus with high precision. 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 an organelle composed of many flat vesicles with the main function of secretion. It is composed of two membrane structures, flat membrane vesicles and vesicles of different sizes. The main function is to process the protein synthesized by the endoplasmic reticulum. Sorting and transportation, and then sent to specific parts of cells or secre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09B57/00G01N1/30
CPCC07D311/82C09B57/00G01N1/30G01N2001/302
Inventor 唐波王慧李平何梓旭
Owner SHANDONG NORMAL UNIV
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