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2-(2-pyridyl)-8-sulfonamidoquinoline derivative, synthesis method and application thereof

A sulfonamidoquinoline and pyridyl technology, which is applied in the field of 2--8-sulfonamidoquinoline derivatives, can solve the problem of the excitation wavelength entering visible light, etc., and achieves improved metal ion binding performance, easy availability of raw materials, and synthetic simple effect

Inactive Publication Date: 2010-07-07
QIQIHAR UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported fluorescent molecular probes synthesized with 8-aminoquinoline as the precursor are difficult to make the excitation wavelength into the visible light.

Method used

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  • 2-(2-pyridyl)-8-sulfonamidoquinoline derivative, synthesis method and application thereof
  • 2-(2-pyridyl)-8-sulfonamidoquinoline derivative, synthesis method and application thereof
  • 2-(2-pyridyl)-8-sulfonamidoquinoline derivative, synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] Dissolve 100mg (0.45mmol) of 2-pyridine-8-aminoquinoline and 357mg (4.52mmol) of pyridine in 10mL of dichloromethane, and add 105mg (0.54mmol) of p-toluenesulfonyl chloride in dichloromethane dropwise under ice-cooling 5mL solution, left at room temperature overnight. The reaction solution was spin-dried and separated by silica gel column chromatography to obtain 102 mg of the product with a yield of 62.1%. mp: 178.7-179.2°C.

[0023] 1 H-NMR (400MHz, CDCl 3 )δ( ＊ 10 -6 ): 9.22(s, 1H), 8.75(d, J=4.0Hz, 1H), 8.60(d, J=5.6Hz, 1H), 8.55(d, J=8.0Hz, 1H), 8.22(d, J =8.4Hz, 1H), 7.95(t, J=8.0Hz, 1H), 7.84(m, 3H), 7.51(d, J=8.4Hz, 1H), 7.47(t, J=8.8Hz, 1H), 7.41(d, J=6.0Hz, 1H), 7.02(d, J=8.0Hz, 2H), 2.32(s, 3H).

Embodiment 2

[0025]

[0026] Operation method is referring to embodiment 1. The product yield is 50.8%. mp: 183.9-185.4°C.

[0027] 1 H-NMR (400MHz, CDCl 3 )δ( ＊ 10 -6 ): 9.23(s, 1H), 8.76(d, J=4.4Hz, 1H), 8.60(d, J=8.8Hz, 1H), 8.52(d, J=8.0Hz, 1H), 8.24(d, J =8.8Hz, 1H), 7.95(t, J=7.6Hz, 1H), 7.84(d, J=8.4Hz, 2H), 7.82(d, J=8.8Hz, 1H), 7.54(d, J=8.4 Hz, 1H), 7.47(t, J=8.4Hz, 1H), 7.42(d, J=6.8Hz, 2H), 7.28(d, J=8.8Hz, 2H).

Embodiment 3

[0029]

[0030] Operation method is referring to embodiment 1. The product yield is 38.8%. mp: 202.4-203.3°C.

[0031] 1 H-NMR (400MHz, CDCl 3 )δ( ＊ 10 -6 )): 9.22(s, 1H), 8.75(d, J=4.4Hz, 1H), 8.58(d, J=8.8Hz, 1H), 8.54(d, J=8.4Hz, 1H), 8.23(d, J=8.8Hz, 1H), 7.96(d, J=7.6Hz, 1H), 7.91(d, J=8.0Hz, 2H), 7.84(d, J=7.6Hz, 1H), 7.51(d, J= 8.4Hz, 1H), 7.46(d, J=7.6Hz, 1H), 7.41(m, 2H), 7.32(t, J=8.0Hz, 2H).

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Abstract

The invention discloses a 2-(2-pyridyl)-8-sulfonamidoquinoline derivative, a synthesis method and a method used for the fluorescence detection of metal ions in solutions and the microscopic fluorescence imaging detection of metal ions in cells. The derivative is prepared by reacting 2-(2-pyridyl)-8-sulfonamidoquinoline and a derivative thereof with sulfonyl chloride and can be used for the fluorescence detection of metal ions in water, alcohol, a DMF (dimethyl formamide) solvent or a DMSO (dimethylsulfoxide) solvent or a mixed solvent of the DMF solvent and the DMSO solvent and the microscopic fluorescence imaging detection of metal ions in microenvironments such as biological tissues, cells, and the like. The invention has the advantages that the metal ion bonding property and the light spectrum property of probe molecules are improved, and the probe molecules can selectively and fluorescently enhance the identification to metal ions such as Zn<2>+, Cd<2+>, and the like in neutral solutions containing water. The excitation wavelength of the probes is longer than 400nm, and the maximum emission wavelength reaches 600nm. The invention obtains a breakthrough progress in the aspect of promoting the working wavelength of TSQ (6methoxy8ptoluene sulfonamidoquinoline) fluorescence molecular probes to enter a visible light region.

Description

technical field [0001] The present invention relates to 2-(2-pyridyl)-8-sulfonylaminoquinoline derivatives, the present invention also relates to the synthetic method of this compound, the present invention also relates to this compound material is used for the fluorescence detection and the metal ion in the solution Microfluorescence imaging detection of metal ions in cells. Background technique [0002] The ubiquity and importance of metal ions in various systems determine that the detection of metal ions is a regular and important task. Therefore, it is necessary to establish a variety of metal ion detection methods to meet various needs. The impact of metal ions on life has been more and more clearly understood, and metal ion fluorescent molecular probes have played an irreplaceable role in it. Since 1987, 6-methoxy-8-p-toluenesulfonamidoquinoline (TSQ) has been used in Zn 2+ Since the fluorescence imaging detection of 8-aminoquinoline as the precursor, the developmen...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D409/14C09K11/06G01N21/64
Inventor 郭祥峰贾丽华张宇徐世成王淼郑丽波王倩倩李辉候亚婷卢冰冰
Owner QIQIHAR UNIVERSITY
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