Synthesis of Multiple Signal Fluorescent Probes and Simultaneous Discrimination of Cys and So 2 , gsh and hcy applications
A fluorescent probe and multi-signal technology, applied in the field of analytical chemistry, can solve the problem that thiol fluorescent probes cannot be distinguished and detected by four channels at the same time
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Embodiment 1
[0027] Example 1. Synthesis of 4-hydroxy-7-(pyrrolidin-1-yl)-2H-chromen-2-one
[0028] a. Diphenyl malonate (6.28 g, 24.51 mmol) and 3-(pyrrolidin-1-yl)phenol (2 g, 12.25 mmol) were added to dry toluene (20 mL) and the reaction mixture was heated to 110 ℃ for 8 hours,
[0029] b. After the reaction was completed, filter, wash the filter cake with n-hexane 3 times, and dry in vacuo to obtain a pale yellow solid 4-hydroxy-7-(pyrrolidin-1-yl)-2H-chromen-2-one (2.0 g, 68% yield).
Embodiment 2
[0030] Example 2. Synthesis of 4-chloro-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde
[0031] . Under nitrogen protection, 1.8 mL of dry re-distilled N,N-dimethylformamide (DMF) was slowly added to an equal volume of phosphorus oxychloride (POCl 3 ), stirring at 20-50 °C for 30 minutes to obtain a red solution,
[0032] . 4-Hydroxy-7-(pyrrolidin-1-yl)-2H-chromen-2-one (1.0 g, 4.32 mmol) was dissolved in 5 mL of N,N-dimethylformamide and added dropwise to step In the mixed solution of , the mixture continued to stir and react at 60 °C for 12 hours under nitrogen protection,
[0033] . After the reaction is complete, the steps The reaction solution in the solution was slowly poured into 500 mL of ice water, and the pH was adjusted to 6 with 20% NaOH solution, resulting in a large amount of precipitation, which was filtered, and the filter cake was washed three times with an appropriate amount of deionized water, and the obtained solid was vacuum-dried to obt...
Embodiment 3
[0035] Example 3. Synthesis of 4-(butylthio)-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde
[0036] . Add 0.20 g (720.19 mmol) 4-chloro-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde and n-butanethiol 64.95 mg (720.19 mmol) to 20 mL In anhydrous dichloromethane, 70 μL of triethylamine was added dropwise, and the reaction was stirred at room temperature.
[0037] . After the reaction is complete, step 4-(butylthio)-2-oxo-7-(pyrrolidin-1-yl)-2H-methylene-3-carbaldehyde was obtained by column chromatography on the reaction liquid.
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