Acyclic nucleoside lead compound and its preparation method and application in pharmacy
A cyclic nucleoside compound, nucleoside compound technology, applied in organic chemistry, anti-tumor drugs, drug combinations, etc., can solve the problem of less research on anti-tumor activity of acyclic nucleoside compounds
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Embodiment 1
[0042]
[0043] Representative test operation: In the reaction flask, add 6-chloropurine (30.9mg, 0.2mmol), L-proline (2.3mg, 0.02mmol) and benzoic acid (2.4mg, 0.02mmol) in sequence, then add 1.5 mL of methanol, and finally trans-2-dodecenal (64.4 μL, 0.3 mmol) was added to the reaction tube, and reacted at room temperature for 24 h. The reaction was detected by TLC (petroleum ether / ethyl acetate=1.5 / 1). After the reaction was completed, it was transferred to an ice-water bath. After the temperature dropped, sodium borohydride (22.7 mg, 0.6 mmol) was slowly added for about 10 minutes. The reaction was detected by TLC (petroleum ether / ethyl acetate=1.5 / 1). After the reaction, add saturated ammonium chloride solution to quench the reaction, add water after vacuum distillation, extract with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, and perform column chromatography on petroleum ether / ethyl acetate (3:1) to obtain white Solid 9b; Mp: 101-102 °C. 1 H...
Embodiment 2
[0099] Synthesis of chiral nucleoside compounds 7b-9b (R-andS-): The general operation is as follows: In the reaction tube, add α,β-unsaturated aldehyde (0.3mmol), catalyst (0.02mmol), benzoic acid (0.02 mmol) and 1.0 mL of anhydrous toluene, stirred at room temperature for 2 h, cooled to -30 °C, added 6-chloropurine (0.2 mmol) into the reaction tube under stirring conditions, and reacted at -30 °C for 48 h. Petroleum ether / ethyl acetate=1.5 / 1 detection reaction. After the reaction was completed, 0.5 mL of methanol was added to the mixed solution while it was kept warm, and then sodium borohydride (0.6 mmol) was added slowly. Slowly raise the temperature to 0°C and react for 30 minutes, and detect the reaction with petroleum ether / ethyl acetate=1.5:1. After the reaction was completed, quenched with saturated ammonium chloride, distilled under reduced pressure, added water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and subjected to column chromatograph...
Embodiment 3
[0118] The present invention synthesizes a series of racemization, R-configuration and S-configuration acyclic nucleoside compounds by using the above method, and tests the cell activity of these compounds on tumor cells by MTT method. The cellular viability of synthetic compounds was assessed using the 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay, with 5 × 10 3 Cells were seeded into 96-well plates and cultured at 37°C / 5% CO 2 24h in the incubator. Then, they were treated with various gradient dilutions of the compound, the control drug 5-FU or the diluent (DMSO) for 48 hours. Replace the medium containing the compound, 5-FU or diluent (DMSO) with 180 μL of fresh medium and 20 μL of MTT solution (5 mg / mL PBS solution), placed at 37 ° C, 5% CO 2 Then, the medium containing MTT was replaced with DMSO (150 μL), and the absorbance of each blank was measured at a wavelength of 570 nm with a microplate reader (Multiskan FC, Thermo), and each concentra...
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