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Hantzsch ester derivative as well as preparation and application thereof

A technology of derivatives and hanchyl esters, applied in the field of pyridine derivatives and their preparation and application, can solve the problems of insufficient specificity, difficulty in preparation, and limitation of use, and achieve the effect of high sensitivity, simple and controllable method

Inactive Publication Date: 2013-09-25
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

O-phenylenediamines, the most widely used and concerned fluorescent molecular probes for NO, still have many phenomena such as the sensitivity being affected by the pH of the medium and the existence of autoxidation due to their own structural characteristics and mechanism of action. Issues such as insufficient specificity limit its use
Other fluorescent probes, such as dansyl copper complexes, boron dipyrrole methyl derivatives, dichlorofluorescein, etc., have disadvantages such as difficulty in preparation and damage to organisms. Those skilled in the art are still working hard to study more Sensitive and easier to prepare fluorescent probes

Method used

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  • Hantzsch ester derivative as well as preparation and application thereof
  • Hantzsch ester derivative as well as preparation and application thereof
  • Hantzsch ester derivative as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: Synthesis of coumarin derivatives based on sonogashira reaction

[0048] 1. Synthesis of 7-methoxycoumarin (7-MC-1)

[0049] The synthetic route is as formula (1). Dissolve 7-hydroxycoumarin (1 g, 6.2 mmol) in 30 mL of acetone, add anhydrous potassium carbonate (1.7 g, 12.35 mmol), and stir at room temperature for 10 min. Add iodomethane (1.05g, 7.41mmol) and heat to reflux for 5h, stop heating, filter while hot, spin the filtrate to dryness, 0.8g of white crystals recrystallized from ethanol, the yield is 73%. 1H NMR (400Hz CDCl 3 )δppm: 7.67(d,1H,J=9.4Hz),7.38(d,1H,J=8.52Hz),6.87(m,2H,J=2.3Hz),6.26(d,1H,J=9.4Hz) ,3.89(s,3H).

[0050] 2. Synthesis of 7-methoxy-3-iodocoumarin (7-MC-2)

[0051] Dissolve 7-MC-1 (1g, 5.68mmol), p-toluenesulfonic acid (TsOH0.98g, 5.68mmol) in 30mL THF (tetrahydrofuran), and slowly add 20mL of THF NIS ( N-iodosuccinimide 1.5g, 6.82mmol) solution. Heated to reflux for 10 h, stopped heating, returned to room temperature, s...

Embodiment 2

[0056] Example 2: UV and fluorescent properties of coumarin derivatives and fluorescent probes

[0057] 1. The ultraviolet and fluorescent properties of coumarin derivatives:

[0058] As shown in Figure 1, the solvents are all K containing 20% ​​DMSO by volume 2 HPO 4 -KH 2 PO 4 buffer solution, the pH value of the solution is 7.4, and the ultraviolet absorption spectrum of 7-methoxycoumarin 7-MC-1 is as Figure 1a , concentration c=5.0×10 -6 mol L -1 , molar absorptivity ε=4.84×10 4 L·mol -1 cm -1 (The abscissa is the wavelength, and the ordinate is the absorbance. The same below) and 7-methoxycoumarin 7-MC-1 ( Figure 1b , c=5.0×10 -6 mol L -1 ,λ ex =324nm,λ em =394nm) fluorescence spectrum (the abscissa is the wavelength, and the ordinate is the fluorescence intensity. The same below).

[0059] As shown in Figure 2, the ultraviolet absorption spectrum of 7-methoxy-3-iodocoumarin 7-MC-2 ( Figure 2a , c=5.0×10 -6 mol L -1 ,ε=5.10×10 4 L·mol -1 cm -1 ) and ...

Embodiment 3

[0067] Embodiment 3: Synthesis of coumarin derivatives based on Hantzsch reaction

[0068]

[0069] The synthetic route is as formula (3). Formula (4) is the reaction formula for reacting with NO.

[0070] 1. Synthesis of 7-hydroxyl-3-methylcoumarin (7-OMe-3a)

[0071] Add (3.0g, 26.6mmol) 2,4-dihydroxybenzaldehyde, (4.5g, 46.8mmol) sodium propionate and (7.5mL, 58.5mmol) propionic anhydride into the reaction flask, slowly add (3mL, 26.6mmol) triethylamine, the dropwise addition is completed, reflux reaction for 12 hours, stop heating, return to room temperature, pour the reaction solution into 100mL water, there is a pink precipitate, filter with suction, use ethyl acetate / petroleum ether=1:2 for the solid Separation by column chromatography yielded 7.7 g of white pure product with a yield of 92%. 1 H NMR (400Hz CDCl 3 )δppm: 9.89(s,1H), 7.58(s,1H), 7.57(d,1H,J=8.0Hz), 6.76(d,1H,J=2.1Hz), 6.62(s,1H), 2.43( s,3H).

[0072] 2. Synthesis of 7-methoxy-3-methylcoumarin (7...

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Abstract

The invention belongs to the field of heterocyclic ring organic compounds, and provides a hantzsch ester derivative with the structure formula in formula I shown in the specification. The invention also provides application of the hantzsch ester derivative as an NO fluorescent probe. According to the technical scheme disclosed by the invention, the specificity effects of the hantzsch ester derivative and NO are utilized to generate characteristics of a corresponding pyridine derivative so as to achieve the response to NO of the fluorescent probe. The NO is detected through the change of the fluorescent characteristics before and after the detection effect. The method is simple and controllable, and the probe is high in sensitivity.

Description

technical field [0001] The invention belongs to the field of heterocyclic organic compounds, and specifically relates to a pyridine derivative and its preparation and application. Background technique [0002] As an important messenger molecule and neuromodulator in organisms, nitric oxide molecule (NO) participates in the regulation of the physiological functions of multiple systems. There is already evidence that nitric oxide is also associated with diseases such as diabetes, Parkinson's disease and Alzheimer's disease. Therefore, NO-donating drugs have attracted extensive attention as potential cardiovascular, anti-tumor, novel anti-inflammatory and anti-Alzheimer's disease drugs. However, NO, as a gas free radical, is extremely unstable in the living body, so the method of detecting NO in the living body has always been a hot spot and difficulty in related research. NO is a free radical gas molecule that can quickly combine with other substances to undergo a chemical r...

Claims

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Application Information

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IPC IPC(8): C07D405/06C07D405/04C09K11/07G01N21/64
Inventor 李敏峰马素芳龚兵何兰
Owner BEIJING NORMAL UNIVERSITY
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