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Synthesis of N-acyl-8-amino quinoline derivatives and use thereof as fluorescent molecular probe

The technology of aminoquinoline and acyl group is applied in the synthesis of N-acyl-8-aminoquinoline derivatives and its application field as a fluorescent molecular probe, which can solve the problems of poor water solubility, short emission wavelength, weak fluorescence and the like, To achieve the effect of enhanced fluorescence intensity, easy availability of raw materials and simple synthesis

Inactive Publication Date: 2009-05-27
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, this type of compound also has disadvantages such as poor water solubility, short emission wavelength (less than 500nm), and relatively weak fluorescence after binding metal ions.
Therefore, sulfonamidoquinoline derivatives have certain limitations in practical application

Method used

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  • Synthesis of N-acyl-8-amino quinoline derivatives and use thereof as fluorescent molecular probe
  • Synthesis of N-acyl-8-amino quinoline derivatives and use thereof as fluorescent molecular probe
  • Synthesis of N-acyl-8-amino quinoline derivatives and use thereof as fluorescent molecular probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Dissolve 288mg (2.0mmol) of 8-aminoquinoline and 222mg (2.8mmol) of pyridine in 10mL of chloroform, add 5mL of chloroform solution containing 461mg (2.4mmol) of chloroacetyl chloride dropwise within 1 hour under ice cooling, Stir at room temperature for 2h to stop the reaction. The reaction liquid was spin-dried and purified by column chromatography, the yield was 79.9%, mp: 131.6-132.6°C. Further 80mg (0.362mmol) 8-chloroacetyl quinoline, 381mg (3.62mmol) aminoethoxyethanol, 468mg (3.62mmol) DIPEA and 20mgKI were added to 30mL acetonitrile, N 2 Under the protection of reflux for 10h, stop the reaction. The reaction solution was spin-dried and purified by column chromatography with a yield of 83.8%. 1 H-NMR (400MHz, CDCl 3 ): 11.24(CONH, s, 1H), 8.86(d, J=5.6Hz, 1H), 8.81(d, J=8.8Hz, 1H), 8.16(d, J=9.6Hz, 1H), 7.53(m , 2H), 7.46(m, 1H), 3.74(OCH 2 CH 2 -OH, m, 4H), 3.59 (COCH 2 , NHCH 2 -CH 2 , m, 4H), 2.99 (CH 2 NH-CH 2 , t, J=4.8Hz, 2H).

Embodiment 2

[0029]

[0030] Operation method is referring to embodiment 1. Yield: 79.4%, mp: 112.4°C. 1H-NMR (400MHz, DMSO): 8.95(d, J=8.0Hz, 1H), 8.69(d, J=8.8Hz, 1H), 8.43(d, J=9.6Hz, 1H), 7.66(m, 3H ), 3.67 (CH 2 -OH, t, J=5.2Hz, 2H), 3.48 (COCH 2 , s, 2H), 3.14 (NH-CH 2 CH 2 OH, t, J=6.4Hz, 2H), 3.09 (NHCH 2 -CH 2 NH, t, J=5.2Hz, 2H), 2.92 (COCH 2 NH-CH 2 , t, J=6.6Hz, 2H).

Embodiment 3

[0032]

[0033] Operation method is referring to embodiment 1. Yield: 62.7%, mp: 183.0-184.2°C. 1 H-NMR (400MHz, DMSO): 8.97 (d, J = 5.2Hz, 1H), 8.63 (d, J = 7.6Hz, 1H), 8.45 (d, J = 9.6Hz, 1H), 8.76 (d, J =8.0Hz, 2H), 7.66(m, 2H), 4.12(COCH 2 , s, 2H), 3.69 (CH 2 -OH, t, J=5.4Hz, 2H), 3.05(CH 2 NH-CH 2 , t, J=5.4Hz, 2H).

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Abstract

The invention relates to the synthesis of N-acyl-8-aminoquinoline derivatives and application thereof as fluorescent molecular probes. The invention takes 8-aminoquinoline as a matrix, can introduce substitutional groups at position 2, 4 and 5 of the quinoline matrix, and can acylate on an amino group to synthesize a series of novel acylaminoquinoline derivatives. The compounds with relatively simple structures and easy synthesis can be used for fluorescence detection of transition and heavy metal ions in solutions, show high sensitivity and selectivity, and are successfully applied to the fluorescence imaging detection of zinc ions in living cells. The compounds are expected to be widely applied in the fields such as analytical inspection of transition metal and heavy metal ions and the catalysis of metal complexes in biological tissues, cells, environment, medicine, and industrial and agricultural production and so on.

Description

technical field [0001] The invention relates to the synthesis of N-acyl-8-aminoquinoline derivatives and the fluorescence detection of transition metals and heavy metal ions as fluorescent molecular probes in solutions, cells and biological tissues. Background technique [0002] Since 1987, 6-methoxy-8-p-toluenesulfonamide quinoline (TSQ) was first used in Zn in brain, heart and other tissue slices 2+ Since the imaging of 8-aminoquinoline, the organic fluorescent molecular compounds designed and developed by using 8-aminoquinoline as the matrix have been developed rapidly for the detection of metal ions in the biological microenvironment. People have been committed to studying the structural characteristics, kinetics and thermodynamic parameters of this kind of compound after complexing with metal ions, and improving its water solubility and membrane permeability, increasing its excitation wavelength, and improving its metal ion complexing ability. Gradually improve the str...

Claims

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Application Information

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IPC IPC(8): C07D215/40C07D413/04C07D401/12C07D401/06G01N33/52C09K9/00
Inventor 郭祥峰贾丽华张宇司万霞徐世成徐智慧
Owner QIQIHAR UNIVERSITY
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