7-diethylamino-3-acetylcoumarin derivative as well as synthesis method and application thereof

A technology based on coumarin and diethylamine, which is applied in the field of 7-diethylamino-3-acetyl coumarin derivatives, can solve the problems of less research and the like, achieves good selectivity, obvious detection signal, Combining simple effects

Active Publication Date: 2021-06-01
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, relatively little research has been done on the 4-position of 7-diethylamino-3-acetylcoumarin

Method used

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  • 7-diethylamino-3-acetylcoumarin derivative as well as synthesis method and application thereof
  • 7-diethylamino-3-acetylcoumarin derivative as well as synthesis method and application thereof
  • 7-diethylamino-3-acetylcoumarin derivative as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation and characterization of Probe 1

[0038] Mix 7-diethylamino-3-acetylcoumarin (1.55g, 6mmol) and 4-methylbenzaldehyde (0.72g, 6mmol) in 30mL absolute ethanol, add 200μL piperidine under stirring, and The mixture was refluxed for 48 hours. Cool to room temperature, filter precipitate and wash with ethanol, then vacuum-dry to obtain orange solid compound (1.25g, yield: 57.6%) namely (E)-7-(diethylamino)-3-(3-(p-toluene base) acryloyl)-2H-chromium-2-one. 1 H NMR (600MHz, Chloroform-d) δ8.57(s, 1H), 8.13(d, J=15.7Hz, 1H), 7.84(d, J=15.7Hz, 1H), 7.61(d, J=7.9Hz ,2H),7.45(d,J=8.9Hz,1H),7.22(d,J=7.8Hz,2H),6.65(d,J=8.9Hz,1H),6.52(s,1H),3.49(q ,J=7.1Hz,4H),2.40(s,3H),1.27(t,J=7.0Hz,6H). 13C NMR(150MHz,Chloroform-d)δ186.62,160.89,158.61,152.72,148.67,143.58,140.74,132.63,131.81,129.55,128.83,123.86,117.03,110.04,108.87,96.91,45.36,45.29,21.59,12.46,12.44 .

[0039] (E)-7-(diethylamino)-3-(3-(p-tolyl)acryloyl)-2H-chromium-2-one (0.36g, 1mmol) and 4-hydrazinobenzoi...

Embodiment 2

[0044] Prepare 2mM Probe 2 fluorescent probe stock solution with dimethyl sulfoxide (DMSO); add 2mL of PBS (pH=7.4) buffer solution and 10μL fluorescent probe stock solution to a fluorescent cuvette, take ClO - The solution is gradually added to the cuvette with a micro-injector, and is detected on the fluorescence spectrophotometer while adding the sample. With ClO - With the addition of , the fluorescence intensity at 520nm gradually weakened and showed a "turn-off" type change. ( Figure 7 )

Embodiment 3

[0046] Prepare 2mM Probe 2 fluorescent probe stock solution with dimethyl sulfoxide (DMSO); add 2mL of PBS (pH=7.4) solution and 10μL fluorescent probe stock solution to the fluorescent cuvette, then add 10 times Equivalents of other analytes and ClO - (1-Blank; 2-Na + ;3-K + ;4-Mg 2+ ;5-Cu 2+ ;6-Zn 2+ ;7-Fe 2+ ;8-Fe 3+ ;9-Al 3+ ;10-Ca 2+ ;11-NO 2 - ;12-NO 3 - ; 13-ClO 2 - ; 14-ClO 3 - ; 15-ClO 4 - ;16-MnO 4 - ;17-Cl - ;18-H 2 o 2 ;19-ClO - ), detected on a fluorescence spectrophotometer ( Figure 8 ). ClO - The fluorescence intensity of the detection system at 520nm is significantly reduced, and other analytes basically do not cause changes in the fluorescence intensity of the detection system.

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Abstract

The invention provides a 7-diethylamino-3-acetyl coumarin derivative as well as a synthesis method and application thereof, the English name of the derivative is 4-(3-(7-(diethylamino)-2-oxo-2H-chrom-3-yl)-5-(p-tolyl)-4, 5-dihydro-1H-pyrazol-1-yl)-4, 5-dihydro-1H-pyrazol-1-yl)-4, 5-dihydro-1H-pyrazol-1-yl)-4, 5-dihydro-1H-pyrazol-1-yl)-benzoic acid, and named as Probe 1; or the English name of the compound is 4-(3-(7-(diethylamino)-4-hydroxy-2-oxo-2H-chrom-3-yl)-5-(p-tolyl)-4, 5-dihydroxy-1H-pyrazol-1-yl)-5-(p-tolyl)-4, 5-dihydroxy-1H-pyrazol-1-yl)-4, 5-dihydroxy-1H-pyrazol-1-yl) benzoic acid, and the compound is named as Probe 2. In a buffer solution of PBS (pH = 7.4), the Probe 1 does not react with ClO <->, and the Probe 2 can realize'turn-off 'type detection of ClO <->. The detection process is simple, sensitive and rapid, and the detection result is accurate.

Description

technical field [0001] The present invention relates to 7-diethylamino-3-acetylcoumarin derivatives, specifically belonging to 7-diethylamino-3-acetylcoumarin derivatives and their synthesis methods, and the derivatives as detection reagents In the detection of ClO - in the application. Background technique [0002] Due to the advantages of easy structure modification and diverse photophysical properties, coumarin has made great progress in the field of chemical biology probes. Coumarin is a dye with a benzopyrone structure, which itself has no fluorescence. The introduction of electron-donating groups at the 3 and 4 positions or electron-withdrawing groups at the 6 and 7 positions will produce strong fluorescence. Coumarin dyes have large Stokes shift, good water solubility and high quantum yield. Due to the small size of coumarin dyes and the ability to penetrate cell membranes, more and more researchers have studied it as a small molecule fluorescent probe for detecti...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07D405/04C09K11/06G01N21/64A61K49/00
CPCC07D405/04C09K11/06G01N21/6428A61K49/0039C09K2211/1088C09K2211/1044C09K2211/1007Y02A50/30
Inventor黄永飞阴彩霞张永斌霍方俊
OwnerSHANXI UNIV