Bile acid compounds, intermediates, preparation methods and applications thereof
A compound and bile acid technology, applied in the direction of steroids, organic chemistry, radioactive carriers, etc., can solve the problems of unsuitable diagnosis of liver cancer cells and low sensitivity
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Embodiment 1
[0213] Synthesis of labeled precursor compounds
[0214] [Example 1] Synthesis of chenodeoxycholyl propargylamine (B3)
[0215] Chenodeoxycholic acid 393mg (1mmol) was added to 30mL CH 2 Cl 2 230 mg (1.2 mmol) of EDC.HCl, 162 mg (1.2 mmol) of HOBt, 280 μL (2 mmol) of triethylamine were added under stirring, and 82.5 μL (1.2 mmol) of propargylamine was added after stirring for several minutes. The above reaction solution was stirred and reacted at room temperature for two days. The reaction solution was washed once with water, once with saturated sodium bicarbonate solution, once with dilute hydrochloric acid, and twice with saturated sodium chloride solution. After the organic layer was dried over anhydrous sodium sulfate, it was purified by column chromatography (developing solvent: petroleum ether, ethyl acetate ). 315.6 mg of white solid was obtained. Yield 73.5%, purity 99% (HPLC).
[0216] The identification data of B3 are as follows: TOF-ESI-MS: M(C 27 h 43 NO 3...
Embodiment 2
[0234] Synthesis of reference compounds
example 1
[0235] [Example 1], the synthesis of the reference compound A'3-B corresponding to A3-B
[0236] Under magnetic stirring, add 170 μL of copper sulfate solution (0.45 mol / L) and 100 μL of sodium ascorbate solution (1.5 mol / L) to 2 mL of pH=6.0 phosphate buffer, mix well and add B3 (25 μmol, 11 mg) in DMF Solution (500 μL), after 10 minutes, add 2-azido-1-fluoroethane in acetonitrile solution (125 μmol, V=3mL), and stir at 50°C for 3 hours. After cooling to room temperature, the reaction solution was diluted with 30 mL of water, and the product was extracted three times with chloroform (15 mL each time). The organic layers were combined, washed with 15 mL of saturated sodium chloride solution, and concentrated under reduced pressure to obtain the product as a white solid. Mass: 11.2 mg, yield: 86.5%, purity 99% (HPLC).
[0237] The identification data of A'3-B are as follows: TOF-ESI-MS: M(C 29 h 47 FN 4 o 3 )=518.71(m / z),519.5[M+H] + ,541.4[M+Na] + .
[0238] 1 H-NMR ...
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