Small-molecule fluorescent probes of phenyl(4-piperidinyl)methanone-like herg potassium ion channels
A technology of fluorescent probes and small molecules, applied in fluorescence/phosphorescence, material analysis through optical means, luminescent materials, etc., can solve the problems of few applications, achieve high sensitivity, mild reaction conditions, and simple preparation methods
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Embodiment 1
[0063] Example 1: N-(2-(4-(4-(methylsulfonamido)benzoyl)-1-piperidinyl)butyl)-1,3-dicarbonyl-2,3-dihydro Preparation of -1H-benzo[de]isoquinoline-6-acetamide (L1):
[0064]
[0065] Concrete synthetic route is as follows:
[0066]
[0067]
[0068] (1) Preparation of Intermediate 1:
[0069] Dissolve 1-acetyl-4-piperidinecarboxylic acid (2.0g, 11.68mmol) in 1,2-dichloroethane (30mL), stir and preheat to 40°C; then add thionyl chloride dropwise into the solution (1.39g, 11.68mmol; dissolved in 5mL 1,2-dichloroethane), after the dropwise addition was completed, the temperature was raised to 65°C for 2 hours, and a white precipitate was formed in the reaction solution. After the reaction was completed, the reaction solution was cooled to room temperature, and N-phenylmethanesulfonamide (2.0 g, 11.68 mmol) and AlCl were added under ice bath conditions. 3 (3.12g, 3.36mmol), stirred for 30min and then refluxed at 80°C for 9h. Pour the reaction solution into crushed ice,...
Embodiment 2
[0082] Example 2: 6-(dimethylamino)-2-(3-(4-(4-methylbenzoyl)-1-piperidinyl)propyl-1H-benzo[de]isoquinoline- Preparation of 1,3(2H)diketones (L4).
[0083]
[0084] Concrete synthetic route is as follows:
[0085]
[0086] (1) Preparation of Intermediate 1:
[0087] Dissolve 1-acetyl-4-piperidinecarboxylic acid (2.0g, 11.68mmol) in 40mL 1,2-dichloroethane, preheat to 40°C; dissolve thionyl chloride (0.85mL, 11.68mmol) In 1,2-dichloroethane (5mL), add dropwise to the preheated solution, then raise the temperature to 65°C and reflux for 2h, cool at room temperature; add toluene (1.08g, 8.1mmol) and Aluminum trichloride (3.12g, 3.36mmol) was stirred for 30min, then heated to 80°C and refluxed for 10h. After the reaction was completed, the reaction solution was poured into crushed ice, extracted with dichloromethane (100mL×3), the organic layers were combined, dried over anhydrous magnesium sulfate, filtered with suction, concentrated and mixed, purified by a silica gel c...
Embodiment 3
[0100] Example 3: Determination of Optical Properties
[0101] Table 1: Optical characteristics of probe molecules
[0102]
[0103] Note: All the above optical properties were measured in phosphate buffer at pH = 7.4.
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