A fluorescent compound for detecting nerve damage and its application
A technology for compounds and neurological disorders, applied in the field of medicine, can solve problems such as poor penetration of excitation and emission light, low fluorescence quantum yield, short absorption and emission wavelengths, etc., achieve high economy and environmental protection, and simple preparation process , the effect of less waste
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Embodiment 1
[0054] Example 1: 2-(4-(9-(diethylamino)-1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzylidene)malononitrile (Compound 1)
[0055]
[0056] Step 1: Dissolve 2-bromo-1,10-phenanthroline-5,6-one) (10.0mmol), potassium carbonate (20.0mmol) and diethylamine (11.0mmol) in 30mL DMF, heat with stirring React at 100°C for 2h, and monitor the progress of the reaction by TLC. Cool to room temperature after the reaction, add 200mL of water to precipitate the solid, wash the filter cake twice with water, and then recrystallize with ethanol to obtain 2-(diethylamino)-1,10-phenanthroline-5 , 6-diketone 2.03g, yield: 72.3%. MS (ESI) M+H: 282.
[0057] Step 2: Dissolve terephthalaldehyde (5.0mmol) and ammonium acetate (50mmol) in 40mL of glacial acetic acid, heat to reflux with stirring, then slowly add 2-(diethylamino)-1,10-phenanthrene A solution of roline-5,6-dione (5.0 mmol) dissolved in 10 mL of glacial acetic acid was continued for 3 h under reflux after the drop was completed, a...
Embodiment 2
[0063] Example 2: 2-(4-(9-(pyrrolidin-1-yl)-1H-imidazo[4,5-f][1,10]phenanthroline-2-yl)benzylidene)propane Dinitrile (Compound 2)
[0064]
[0065] Step 1: Dissolve 2-bromo-1,10-phenanthroline-5,6-one) (10.0mmol), potassium carbonate (20.0mmol) and tetrahydropyrrole (11.0mmol) in 30mL DMF, heat with stirring React at 100°C for 4h, and monitor the progress of the reaction by TLC. Cool to room temperature after the reaction, add 150mL of water to precipitate the solid, filter and wash the filter cake twice with water, and recrystallize with methanol to obtain 2-(pyrrolidin-1-yl)-1,10-phenanthroline -5,6-dione 2.27g, yield: 81.4%. MS (ESI) M+H: 280.
[0066] Step 2: Dissolve terephthalaldehyde (5.0mmol) and ammonium acetate (50mmol) in 50mL of glacial acetic acid, heat to reflux with stirring, then slowly add 2-(pyrrolidin-1-yl)-1,10 - A solution of phenanthroline-5,6-dione (5.0mmol) dissolved in 15mL of glacial acetic acid, and continued to reflux for 5h after the drop wa...
Embodiment 3
[0072] Example 3: Absorption and Fluorescence Spectra of Compounds of the Invention.
[0073] Taking compound 2 as an example, the absorption and fluorescence spectra of the compounds of the present invention in different solvents were tested.
[0074] Compound 2 was dissolved in dimethyl sulfoxide to prepare a 10 mM stock solution, and stored in a refrigerator at 4° C. in the dark for future use. Take 10 μL of the mother solution, dilute it to a concentration of 10 μM with DMSO, ethanol and PBS, and measure its absorption spectrum, the results are as follows: figure 1 shown. The maximum absorption wavelengths of compound 2 in DMSO, ethanol and PBS are 607nm, 603nm and 611nm respectively.
[0075] Excited with light at 610nm, the fluorescence spectrum of compound 2 was tested, and the results were as follows figure 2 shown. The maximum emission wavelengths of compound 2 in DMSO, ethanol and PBS are 686nm, 685nm and 663nm, respectively.
[0076] The above experimental re...
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