Azine hydrazine compound, and preparation method and application thereof

A compound and hydrazine technology, applied in the field of azine hydrazine compounds and their preparation, can solve the problems of difficult detection and fluorescence analysis, decrease in fluorescence quantum yield, high non-radiative transition ratio, etc., and achieve good solubility, The effect of increasing Stokes displacement and enhancing AIE performance

Active Publication Date: 2018-12-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, the rapid intramolecular free rotation effect in the conventional hydrazine structure (the lone pair of electrons is small in size, prone to cis-trans isomerization) and the high non-radiative transition ratio in the aggregated state lead to a decrease in its fluorescence quantum yield Seriously, it is difficult to apply to detection and fluorescence analysis under conventional water system conditions, such as the study of intracellular substructure, specific recognition of bacteria, monitoring of metal ions in water systems, etc.

Method used

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  • Azine hydrazine compound, and preparation method and application thereof
  • Azine hydrazine compound, and preparation method and application thereof
  • Azine hydrazine compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] According to the following synthetic route, the following compounds are specifically synthesized:

[0056]

[0057] (1) Synthesis of Compound 2

[0058] A mixture of compound 1 (1.1 g, 2 mmol) and excess hydrazine hydrate was stirred under reflux for 4 hours. After the reaction was completed, the solvent and the remaining hydrazine hydrate were removed by rotary evaporation to obtain compound 2 as a transparent oil with a yield of 100% (1.2 g).

[0059] (2) Synthesis of compound M1-DPAN

[0060] Compound 2 (0.57 g, 1 mmol) and compound 3 (0.258 g, 1.5 mmol) were stirred under reflux for 4 hours. After the reaction was completed, it was separated with a chromatographic silica gel column, and the eluent used was methanol: acetone: dichloromethane = 1:16:30 to obtain a yellow solid compound M1-DPAN with a yield of 20.8% (0.13g).

[0061] 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):12.68(s,1H),8.88(s,1H),8.28(d,J=8.3Hz,1H),7.73(d,J=8.1Hz,1H),7.71–7.66 (m,2H),7.53–7.50(m,...

Embodiment 2

[0065] Example 2: Compounds in Example 1 are used for fluorescent staining of Gram-positive bacteria

[0066] (1) Bacterial culture

[0067] a. A single colony of Staphylococcus aureus (Gram-positive) was inoculated in 5 mL of NB medium, and cultured at 37° C. for 12 hours. Afterwards, the colony was centrifuged at 7100 rpm for 1 minute, while washing three times with phosphate buffered saline (PBS, 10 mM, pH=7.4), the supernatant was discarded, and the remaining Staphylococcus aureus was suspended in PBS, and then diluted at 600 nm to 1.0 optical density (OD 600 = 1.0). Bacillus subtilis (Gram-positive), Enterococcus faecalis (Gram-positive), Pseudomonas aeruginosa (Gram-negative), Escherichia coli (Gram-negative), S. Yeast (fungus) and Candida albicans (fungus).

[0068] b. Mixed strains (Saccharomyces cerevisiae, Bacillus subtilis and Pseudomonas aeruginosa) were co-stained with M1-DPAN at a concentration of 5 μM in PBS buffer solution at 37°C for 20 minutes, and then c...

Embodiment 3

[0080] According to the following synthetic route, the following compounds are specifically synthesized:

[0081]

[0082] (1) Synthesis of Compound M2-DPAN

[0083] Compound 2 (0.57 g, 1 mmol) and compound 4 (0.258 g, 1.5 mmol) were stirred under reflux for 4 hours. After the reaction was completed, it was separated by a chromatographic silica gel column, and the eluent used was methanol:dichloromethane=1:15 to obtain a yellow solid compound M2-DPAN with a yield of 15.3% (0.096g).

[0084] 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):13.08(s,1H),9.72(s,1H),8.18(d,J=8.5Hz,1H),7.76(t,J=8.1Hz,2H),7.73–7.68 (m,2H),7.57–7.51(m,1H),7.38–7.33(m,1H),7.32–7.28(m,2H),7.09(d,J=9.0Hz,1H),7.03–6.99(m ,2H),6.94–6.88(m,2H),4.06–3.98(m,4H),3.74(dd,J=9.1,4.5Hz,8H),2.47(br,8H),2.42–2.30(m,4H ),1.89–1.75(m,5H),1.63–1.47(m,8H),1.46–1.35(m,4H).

[0085] 13 C NMR (125MHz, CDCl 3 ),δ(TMS,ppm):167.32,161.38,160.98,159.78,159.62,134.01,132.71,130.90,130.69,130.32,129.06,128.00,127.68,123.46,120.0...

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Abstract

The invention discloses an azine hydrazine compound containing phenol, an N=N bond, a diphenyl group, and a morpholine ring, and also discloses a preparation method of the azine hydrazine compound. The method includes the steps of: heating a diphenyl hydrazine derivative and arylsalicylaldehyde in a solvent at 20-150 DEG C to carry out a reaction for 1-24 h, and separating and purifying a reactionproduct to obtain the azine hydrazine compound. The invention also discloses an application of the compound for specific identification and tracking of gram-positive bacteria. The azine hydrazine compound has a significant property of aggregation-induced emission (AIE) and great solubility, has significant fluorescent staining capability on cells or bacteria, and has great application prospect.

Description

technical field [0001] The invention relates to the technical field of analysis and detection materials, in particular to an azine hydrazine compound and its preparation method and application. Background technique [0002] With the rapid development of the country's economy, science and technology and the continuous improvement of people's living standards, real-time monitoring of personal health, disease prevention and treatment have gradually become people's livelihood issues that people pay more attention to. Compared with the delay of traditional in vitro chemical testing and the harmfulness of online radiation detection, fluorescence online imaging technology has gradually entered people's field of vision with its advantages of high efficiency, greenness and strong real-time performance, and has been widely used in cellular immunology, microbiology, etc. Science, molecular biology, genetics, neurobiology, pathology, oncology, clinical laboratory science, medicine, bota...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/088C07D295/135C07D295/15C09K11/06G01N21/64G01N21/84
CPCG01N21/6428G01N21/84C09K11/06C07D295/088C07D295/135C07D295/15C09K2211/1033C09K2211/1011C09K2211/1007
Inventor 唐本忠王志明胡蓉周凡秦安军
Owner SOUTH CHINA UNIV OF TECH
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