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Long wavelength type H2S fluorescence probe, compounding method and application thereof

A technology of fluorescent probe and synthesis method, which is applied to long-wavelength H2S fluorescent probe and its synthesis and application fields, can solve the problems of long response time, short emission wavelength, complex synthesis route, etc., and achieves high selectivity and good sensitivity , the effect of easy separation and purification process

Inactive Publication Date: 2017-11-24
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these literatures can specifically identify hydrogen sulfide, the reported fluorescent probes still have certain limitations, such as complex synthetic routes, short emission wavelengths, and long response times. Therefore, it is necessary to design and synthesize better H 2 S fluorescent probe is of great significance

Method used

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  • Long wavelength type H2S fluorescence probe, compounding method and application thereof
  • Long wavelength type H2S fluorescence probe, compounding method and application thereof
  • Long wavelength type H2S fluorescence probe, compounding method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: The specific synthetic steps of compound 2 are as follows:

[0035]

[0036]Compound 1,4-diethyl-1,2,3,4-tetrahydro-7-hydroxyquinoxaline-6-al (468mg, 2mmol), ethyl acetoacetate (260mg, 2mmol) and piperidine 0.1mL Dissolve in ethanol and reflux for 4 hours, then pour the solution into hydrochloric acid (4mol / L, 10mL), stir at 60°C for 30 minutes, mix the solution with water, extract with ethyl acetate (3×80mL), and wash with anhydrous sulfuric acid After drying over sodium, the crude product was purified by silica gel column chromatography using EA:PE=1:5 (v / v) as the eluent, and 420.5 mg of compound 2 was isolated with a yield of 70%. 1 H NMR (400MHz, CDCl 3 )δ8.38(s,1H),6.48(s,1H),6.39(s,1H),3.59-3.52(m,2H),3.42(q,J=7.1Hz,2H),3.32(q,J =7.1Hz, 2H), 3.26-3.20(m, 2H), 2.67(s, 3H), 1.20(dt, J=15.9, 7.1Hz, 6H).

Embodiment 2

[0037] Embodiment 2: The specific synthetic steps of compound 1 are as follows:

[0038]

[0039] Compound 2 (300.4mg, 1mmol), p-hydroxybenzaldehyde (134.2mg, 1.1mmol), and piperidine (0.1mmol) were dissolved in toluene and refluxed for 4h, then hydrochloric acid (4mol / L, 15mL) was added and stirred at 40°C For 50 minutes, add water to the solution, then extract with ethyl acetate (3×100mL), dry the organic layer over anhydrous sodium sulfate, and purify the crude product by silica gel column chromatography using EA:PE=1:2 (v / v) As eluent, 179.8 mg of compound 1 was isolated with a yield of 44%. 1 H NMR (400MHz, DMSO-d 6 )δ10.01(s,1H),8.48(s,1H),7.82(d,J=15.7Hz,1H),7.56(d,J=15.7Hz,1H),7.51(d,J=8.2Hz, 2H), 6.76-6.83(m, 3H), 6.51(s, 1H), 3.51(t, J=5.1Hz, 2H), 3.45(q, J=7.1Hz, 2H), 3.27(d, J=7.1 Hz, 2H), 3.15 (t, J=5.1Hz, 2H), 1.08 (dt, J=13.2, 5.1Hz, 6H).

Embodiment 3

[0040] Embodiment 3: The specific synthetic steps of fluorescent probe L are as follows:

[0041]

[0042] Compound 1 (404.5mg, 0.5mmol), 2,4-dinitrofluorobenzene (186mg, 1.0mmol), potassium carbonate (187mg, 1.35mmol), dissolved in DMF (5mL) and stirred, reacted at room temperature for 3h . After the reaction was completed, it was quenched with water, extracted with ethyl acetate (3×100mL), dried over anhydrous sodium sulfate, and the solvent was spinned out to obtain the crude product, which was purified by silica gel column chromatography using PE:PE=1:10 (v / v) was used as eluent to obtain 285.3 mg of probe L, yield 50%. 1 H NMR (400MHz, DMSO-d 6 )δ8.92(s,1H),8.55(s,1H),8.46(s,1H),7.69-8.06(m,4H),7.29-7.34(m,3H),6.88(s,1H),6.57 (s,1H),3.21-3.56(m,8H),1.13-1.21(m,6H). 13 C NMR (101MHz, DMSO-d 6 )δ185.77,162.73,160.79,155.52,154.79,153.65,148.08,144.30,142.17,140.45,140.04,133.46,132.76,131.11,130.12,126.24,122.38,121.09,120.38,114.75,109.10,108.14,95.08,47.59,46.03 ...

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Abstract

The invention relates to a preparation method for a long-wavelength fluorescence-enhanced fluorescence probe capable of fast recognizing H2S in an aqueous medium and application of the fluorescence probe in detection of H2S. The molecular structural formula is as shown in the specification. The fluorescence probe has the advantages of high selectivity, high anti-jamming capability, high sensitivity, application in fluorescence detection for H2S in environmental and biological samples and wide application prospect.

Description

technical field [0001] The invention relates to a long-wavelength recognition method based on tetrahydroquinoxalinopyrone derivatives 2 S fluorescent probes and their synthesis methods and applications. Background technique [0002] It is well known that hydrogen sulfide (H 2 S) is a poisonous gas with the smell of rotten eggs, which mainly comes from volcanic eruptions and mammalian cells themselves through cystathionine-β-synthase (CBS), cystathionine-γ-lyase (CSE), Produced by enzymes such as 3-mercaptopyruvate thiotransferase (3-MST). Hydrogen sulfide is a gas signal molecule, which has become a research hotspot in the field of biology in recent years due to its multiple roles in physiological and pathological processes. Previous studies have shown that endogenous H 2 S can affect the cardiovascular, nervous, immune, endocrine, digestive systems, etc., and its anti-oxidative and anti-apoptotic signal transduction effects are also manifested as induced heart failure. ...

Claims

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Application Information

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IPC IPC(8): C07D491/052C09K11/06G01N21/64
Inventor 钟克利邓隆隆曲秀莉侯淑华朱文慧任欢欢步营赵杰汤立军
Owner BOHAI UNIV
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