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Pyrazoline derivatives, and preparation method and application thereof

A derivative, pyrazoline technology, applied in the application field of Zn2+ fluorescent probes, can solve the problems of rare ion probes and achieve good selectivity

Inactive Publication Date: 2014-05-28
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, although there are reports in the literature on the use of fluorescence techniques to detect Zn 2+ , but Zn with pyrazoline derivatives as the main structural unit 2+ Ion probes are still rare
In previous studies, we developed a pyrazoline derivative as Zn 2+ Ion probes can be used for fluorescence detection in acetonitrile and water, but the fluorescence enhancement is only 4 times【Sensors&Actuators:B.Chemical.2011,159,148-153】

Method used

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  • Pyrazoline derivatives, and preparation method and application thereof
  • Pyrazoline derivatives, and preparation method and application thereof
  • Pyrazoline derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 preparation of pyrazoline derivatives

[0023] Dissolve m-methyl-o-hydroxyacetophenone (1) (12g), o-allyloxybenzaldehyde (2) (13g), sodium hydroxide (48g) in 150ml ethanol, react in ice-water bath for 8h, and judge by TLC After the reaction, add dilute hydrochloric acid solution to neutralize to pH = 7, filter to obtain the crude reaction product, recrystallize with 40ml ethanol, filter and drain to obtain chalcone derivative (3) (18.546g), orange-red crystals, yield 78.8%. The melting point is 166-167°C.

[0024] H NMR spectrum determination: 1 H NMR (300MHz, CDCl 3 ):2.34(s,3H,CH 3 ),4.67(dt,2H,J=5.4,1.5Hz,CH 2 in allyloxy moiety), 5.36 (dd, 1H, J ABcis =9,J BC =1.5Hz,=CHH),5.50(dd,1H,J ACtrans =19,J BC =1.5Hz,=CHH),6.10-6.23(m,1H,=CH-),6.93(d,1H,J=8.4Hz,ArH),6.95(t,1H,J=8.7Hz,ArH),7.31 (d,1H,J=8.4Hz,ArH),7.38(t,1H,J=8.4Hz,ArH),7.65(d,1H,J=8.4Hz,ArH),7.69(s,1H,ArH), 7.87(d,1H,J trans =15.6Hz,=CH-,conjugated vinyl),8.19(d,1H,J trans =15.6Hz,=...

Embodiment 2

[0025] Example 2 Preparation of Pyrazoline Derivatives (4)

[0026] Dissolve compound 3 (5.882g), thiosemicarbazide (2.73g), and sodium hydroxide (2.4g) in 70ml of ethanol, heat and reflux for 4h, after TLC judges that the reaction is over, neutralize the reaction mixture with dilute hydrochloric acid to pH= 7. The crude product was obtained by filtration and recrystallized with 300ml of ethanol to obtain the product pyrazoline derivative (4), a white solid with a yield of 52% and a melting point of 233-234°C.

[0027] Infrared spectrum measurement: IR (KBr), υ: 3436.6, 3326.8, 1600.4, 1481.1, 1337.7, 1250.9, 816.8, 746.7cm -1 .

[0028] H NMR spectrum determination:1 H NMR (300MHz, CDCl 3 ):2.27(s,3H,CH 3 ),3.25(dd,1H,J=18,3.6Hz,CHH in pyrazoline moiety),3.90(dd,1H,J=18,11.4Hz,CHH in pyrazoline moiety),4.57(d,2H,J=5.4Hz ,CH 2 in allyloxy moiety), 5.23 (d, 1H, J ABcis =10.5Hz,=CH),5.37(d,1H,J ACtrans =17.1,=CHH),5.93-6.06(m,1H,=CH-),6.24(dd,1H,J=11.4,3.6Hz,CH in pyrazo...

Embodiment 3

[0033] Embodiment 3 Fluorescence spectrophotometry test

[0034] Use a micro syringe to add 10 equivalents of Na + ,Mg 2+ ,Al 3+ , K + , Ca 2+ ,Cr 3+ ,Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ , Ag + ,Cd 2+ , Ba 2+ ,Pb 2+ ,Hg 2+ and Cu 2+ Ionic aqueous solutions were tested by fluorescence spectrophotometry.

[0035] The result is as figure 1 , showing that the pyrazoline derivative (4) on Zn 2+ It has very good selectivity, and the contrast before and after adding zinc ions shows that the fluorescence is enhanced by 40 times, and has a strong fluorescence enhancement effect.

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Abstract

The invention discloses a preparation method of pyrazoline derivatives and application of the pyrazoline derivatives as a Zn<2+> fluorescent probe. The structural formula of the pyrazoline derivatives is disclosed as Formula (I). The pyrazoline derivatives do not fluoresce, and the fluorescence can be enhanced by 40 times after the pyrazoline derivatives act with Zn<2+> in an EtOH / HEPES (20mM, pH 7.2, 1:1 volume ratio) buffer solution. When being used as a Zn<2+> fluorescent probe, the pyrazoline derivatives have high selectivity, have the fluoroscopic examination limit of 6.1*10<-7>M for Zn<2+>, and can be used for fluorescent imaging and locating detection of Zn<2+> in PC12 cells.

Description

technical field [0001] The present invention relates to a kind of pyrazoline derivative and its preparation method and its use as Zn 2+ Application of fluorescent probes. Background technique [0002] As the second largest transition metal element in the human body, zinc plays a very important role in the human body. Numerous zinc ion-centered enzymes and proteins linked to DNA all play a pivotal role in the human body. Although zinc ions (Zn 2+ ) is tightly linked to enzymes and proteins when acting, but free Zn 2+ It is still present in numerous human tissues such as the brain, gut and retina. Therefore, today's chemical research and biological research fields are in urgent need of a high-efficiency detection Zn 2+ s method. [0003] At present, although there are reports in the literature that the use of fluorescence techniques to detect Zn 2+ , but Zn with pyrazoline derivatives as the main structural unit 2+ Ion probes are still rare. In previous studies, we de...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/06C12Q1/02
Inventor 赵宝祥苗俊英张尚立张喆王方悟
Owner SHANDONG UNIV
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