Novel ecdysterone synthetic derivative and preparation method and application thereof
A technology of compounds, drugs, applied in the field of natural medicinal chemistry
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Embodiment 1
[0063] 20-Hydroxy-β-ecdysterone (ie, TA, 1.54 g, 3.21 mmol) and phenylboronic acid (412 mg, 3.38 mmol) were dissolved in 20 mL of DMF. After stirring at room temperature for 8 h, 40 mL of saturated brine was added and the reaction solution was diluted with 150 mL of ethyl acetate. The organic layer was washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a white solid. The crude product was directly subjected to the next reaction without further purification.
[0064] The above crude product and p-toluenesulfonic acid (55 mg, 0.32 mmol) were dissolved in 40 mL of acetone and 2,2-dimethoxypropane (i.e. formula III, wherein R 1 , R 2 , R X and R Y Respectively methyl) in equal volumes of mixed solvents. After stirring at room temperature for 12h, add 10mL NaHCO 3 The reaction was quenched, and the organic solvent was concentrated off. The residue was diluted with 150 mL EtOAc, washed with saturated brine (50 mL×3...
Embodiment 2
[0067] With compound 1 (being formula IV compound, wherein R 1 and R 2 Methyl) (1.95g, 3.21mmol), imidazole (656mg, 9.63mmol) and DMAP (40mg, 0.33mmol) were dissolved in 40mL CH 2 Cl 2 , add TESCl dropwise to the solution at room temperature (i.e. the compound of formula V, where R 3 , R 4 and R 5 each independently ethyl; X is chlorine) (1.13 mL, 6.43 mmol). After stirring at room temperature for 4 h, the reaction solution was diluted with EtOAc (150 mL), washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was separated by silica gel column chromatography (17% EtOAc / petroleum ether) to obtain compound 2 (2.11 g, yield 91%) as white foam. 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=7.2Hz, 2H), 7.46(t, J=7.2Hz, 1H), 7.36(t, J=7.2Hz, 2H), 5.82(s, 1H), 4.26-4.21( m, 2H), 4.13-4.09(m, 1H), 2.84(t, J=2.84, 1H), 2.38-2.34(m, 2H), 2.11-2.04(m, 3H), 2.04-1.81(m, 7H ), 1.78-1.57(m, 4H), 1.54-1.45(m, 1H), 1.50(s, 3H), 1.34(...
Embodiment 3
[0070] Compound 2 (2.17 g, 3.01 mmol) was dissolved in 30 mL CH 2 Cl 2 After that, 1M NaOH (20 mL) and 30% H 2 o 2 (10 mL). After stirring at room temperature for 30 minutes, the reaction solution was diluted with EtOAc (100 mL), and the organic layer was separated. The organic layer was washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was separated by silica gel column chromatography (25% EtOAc / petroleum ether) to obtain compound 3 (1.88 g, yield 98%) as white foam. 1 HNMR (400MHz, CDCl 3)δ5.82(d, J=0.8Hz, 1H), 4.27-4.20(m, 2H), 3.42(d, J=10.4Hz), 2.81(t, J=8.4Hz, 1H), 2.36-2.30( m, 2H), 2.11-2.03(m, 4H), 1.98-1.93(dd, J=14.4, 5.6Hz, 1H), 1.88-1.81(m, 2H), 1.78-1.66(m, 6), 1.62- 1.46(m, 2H), 1.48(s, 3H), 1.37-1.32(m, 1H), 1.32(s, 3H), 0.98(s, 3H), 0.95(t, J=8.0Hz, 9H), 0.86 (s, 3H), 0.59 (q, J=8.0Hz, 6H); 13 C NMR (50MHz, CDCl 3 )δ202.7, 163.3, 121.4, 108.3, 84.9, 76.6, 73.9, 72.2, 71.6, 50.8, 49.1, 4...
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