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Substitution coumarin-pyridine derivative, preparing method thereof and application thereof

A technology of coumarin and derivatives, applied in chemical instruments and methods, instruments, analytical materials, etc., can solve the problems of small Stokes shift and low fluorescence quantum yield, and achieve large Stokes shift, The effect of simple and easy to obtain raw materials and excellent selectivity

Active Publication Date: 2016-01-06
SICHUAN UNIV
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Problems solved by technology

Existing reports have identified some SOs based on the coumarin skeleton 2 However, there are small Stokes shifts, low fluorescence quantum yields, and the need for organic solvents as co-solvents to limit their applications [see: (a) Y.-Q.Sun, J .Liu, J.Y.Zhang, T.Yang and W.Guo, Chem.Commun., 2013, 49, 2637–2639. (b) M.-Y.Wu, T.He, K.Li, M.-B.Wu, Zh. Huang and X.-Q. Yu, Analyst., 2013, 138, 3018. (c) Ch. Ch. Wang, Sh. Feng, L. Y. Wu, Sh. Y. Yan, Ch. Zhong, P. Guo, R. Huang, X.Ch.Weng, X.Zhou, Sensors and Actuators B., 2014,190,792–799.], in addition, only a few reported probes can detect endogenous SO 2 [See: (a) M.–Y.Wu, K.Li, Ch.–Y.Li, J.–T.Hou and X.–Q.Yu, Chem.Commun., 2014, 50, 183. (b)W. Xu, Ch. L. Teoh, J. Peng, D. Su, L. Yuan, Y.–T. Chang, Biomaterials., 2015, 03, 038. (c) Y. Liu, K. Li, M.-Y. Wu, Y.-H. Liu, Y.-M. Xie and X.-Q. Yu, Chem. Commun., 2015, 51, 10236-10239.]

Method used

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  • Substitution coumarin-pyridine derivative, preparing method thereof and application thereof
  • Substitution coumarin-pyridine derivative, preparing method thereof and application thereof
  • Substitution coumarin-pyridine derivative, preparing method thereof and application thereof

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preparation example Construction

[0028] The preparation method of the substituted coumarin-pyridine derivative comprises the following steps:

[0029] a. Dissolve 3-cyano-4-methylpyridine and methyl iodide in toluene, stir at room temperature for 3 to 6 hours and then reflux for 20 to 40 minutes to prepare intermediate 1; the amount of methyl iodide 1.1 to 1.5 times the equivalent of 3-cyano-4-methylpyridine;

[0030] b. Dissolving the substituted coumarin aldehyde and intermediate 1 in acetic anhydride, and reacting under reflux for 3-6 hours to prepare a substituted coumarin-pyridine derivative. The amount of the intermediate 1 is 2 to 2.5 times the equivalent of the substituted coumarin aldehyde.

[0031] In the embodiment of the present invention, HeLa cell line was purchased from ATCC (American Type Culture Collection), 10% fetal bovine serum was purchased from Hyclone Company, and DMEM (H) medium was purchased from Gibco Company of the United States. The nuclear dye NucBlue and the mitochondrial dye M...

Embodiment 13

[0032] Synthesis of Example 13-cyano-4-methyl-1-picoline (intermediate 1)

[0033]

[0034] 3-Cyano-4-picoline (5.9 g, 50 mmol) and iodomethane (10.8 g, 55 mmol) were dissolved in toluene, and the reaction was stirred at room temperature for 4 hours and then refluxed for 30 minutes. After cooling the reaction solution, it was filtered with suction, and the obtained solid was washed with ether and dried to obtain 9.65 g (37.1 mmol) of a light yellow solid with a yield of 74.2%.

[0035] 1 HNMR (400MHz, DMSO): δ9.63(s, 1H), 9.09(d, J=6.4Hz, 1H), 8.25(d, J=6.4Hz, 1H), 4.31(s, 3H), 2.78(s ,3H).

Embodiment 23

[0036] Synthesis of Example 23-(Iodide 1-methyl-3-cyano-pyridine vinyl)-7-cyclohexanediaminocoumarin (compound 2)

[0037]

[0038] The compound cyclohexanediaminocoumarin aldehyde (53mg, 0.2mmol) and intermediate 1 (104mg, 0.4mmol) were dissolved in 5mL of acetic anhydride, refluxed and stirred at 120°C for 4 hours, after the reaction was complete, cooled to room temperature for pumping Filter, wash with ice ethanol and dry to obtain 72.1 mg (0.14 mmol) of a dark green solid with a yield of 70.5%.

[0039] 1 HNMR (400MHz, DMSO): δ9.45(s, 1H), 8.87(d, J=6.8Hz, 1H), 8.50(d, J=7.0Hz, 1H), 8.15(t, J=7.6Hz, 2H ), 7.85(d,J=15.4Hz,1H), 7.22(s,1H), 4.18(s,3H), 3.40(s,4H), 2.75(d,J=12.4,6.2Hz,4H), 1.92 (s,4H).

[0040] 13 CNMR (101MHz, DMSO): δ159.86(s), 154.79(s), 152.13(s), 150.63(s), 149.27(s), 148.55(s), 146.24(s), 143.48(s), 127.65 (s), 120.93(s), 120.47(s), 117.56(s), 114.09(s), 111.89(s), 109.13(s), 107.89(s), 105.54(s), 50.33(s), 49.77(s), 47.33(s), 27.16(s), 20.96(s)...

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Abstract

The invention belongs to the field of organic chemistry, and particularly relates to a substitution coumarin-pyridine derivative, a preparing method thereof and an application thereof. The structural formula of the substitution coumarin-pyridine derivative is shown as the first formula (please see the specification). In addition, the invention provides the preparing method of the compound and the application of the compound to detection of endogenous SO2 in living cells. The substitution coumarin-pyridine derivative has the advantages of being good in water solubility, high in SO2 selectivity, low in detection limitation, small in toxicity, high in quantum yield, large in Stokes shifting, mild in overall reaction condition, low in cost, capable of achieving detection of the endogenous SO2 in the living cells and the like at the same time; the defects that as for an existing SO2 detection small-molecular fluorescent probe, organic solvents need to serve as cosolvents, and the quantum yield is low are overcome, and a new choice is provided for detecting the endogenous SO2 in the living cells.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a substituted coumarin-pyridine derivative, a preparation method and application thereof. Background technique [0002] SO 2 It is an environmental pollutant produced by fossil fuel and coal combustion, which plays an important role in environmental and physiological processes. It can be used in food to prevent food spoilage, inhibit bacterial growth and proliferation, and is also closely related to some cancer diseases such as lung cancer, cardiovascular diseases, and neurological disorders such as stroke, migraine, brain cancer and other diseases. Inhalation of excess SO 2 It will change the properties of potassium ion and sodium ion channels, thereby disrupting the redox balance of cells. Therefore, for intracellular SO 2 The detection has become a hotspot in the field of biochemistry. [0003] Compared with existing technologies such as electrochemical analysi...

Claims

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Application Information

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IPC IPC(8): C07D455/04C07D491/16C09K11/06G01N21/64
CPCC07D455/04C07D491/16C09K11/06C09K2211/1048G01N21/6428
Inventor 余孝其李坤杨晋
Owner SICHUAN UNIV
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