Imidazole derivative as antiviral agent and pharmaceutical application thereof
A pharmacy and compound technology, applied in the preparation of medicines for treating viral infections, the field of imidazole derivatives for treating respiratory syncytial virus infection, can solve the problems that the activity and solubility need to be improved, etc.
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Embodiment 1
[0202] 1-((1-(4-Hydroxybutyl)-1H-benzo[d]imidazol-2-yl)methyl)-2',3',5',6'-tetrahydrospiro[indoline Indole-3,4'-pyran]-2-one
[0203]
[0204]
[0205] first step
[0206] 4-((2-nitrophenyl)amino)butyl-1-ol
[0207] 1-fluoro-2-nitrobenzene 1a (6.73 g, 47.75 mmol) was dissolved in 70 mL of 1,4-dioxane, and 4-aminobutyl-1-ol (5.1 g, 57.3 mmol) and triethylamine (7.23 g, 71.63 mmol) were added , stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the crude product was added to 100 mL saturated aqueous sodium bicarbonate solution, extracted with dichloromethane (100 mL×2), and the organic phases were combined, washed with water (100 mL×2) and saturated sodium chloride solution ( 100 mL×2), dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the product 4-((2-nitrophenyl)amino)butyl-1-ol 1b (9.31 g, orange-red oil), the product was directly subjected to...
Embodiment 2
[0239] 1-((1-(4-Hydroxybutyl)-1H-benzo[d]imidazol-2-yl)methyl)-spiro[indoline-3,4’-piperidin]-2-one
[0240]
[0241]
[0242] first step
[0243] 1’-Benzylspiro[indoline-3,4’-piperidin]-2-one
[0244] indolin-2-one 2a (5 g, 37.55 mmol) dissolved in 50 mL THF, -60 o C was added NaHMDS (187.8 mL, 187.8 mmol), -60 o C was stirred for 0.5 hour, N-benzyl-2-chloro-N-(2-chloroethyl) diethylamine was added, and the reaction solution was stirred at room temperature for 18 hours. The reaction solution was poured into 200 mL ice water, extracted with ethyl acetate (100 mL×2), the organic phases were combined, washed with water (50 mL×3), saturated sodium chloride solution (50 mL×2), and washed with anhydrous sulfuric acid Na-dried, filtered, the filtrate concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with eluent system B to obtain 1'-benzylspiro[dihydroindoline-3,4'-piperidine]-2- ketone 2b (2 g, colorless oi...
Embodiment 3
[0260] 1-((5-bromo-1-(4-hydroxybutyl)-1H-benzo[d]imidazol-2-yl)methyl)-2',3',5',6'-tetrahydrospiro [Indoline-3,4'-pyran]-2-one
[0261]
[0262]
[0263] first step
[0264] 4-((4-Bromo-2-nitrophenyl)amino)butyl-1-ol
[0265] 4-bromo-1-fluoro-2-nitrobenzene 3a (10.45 g, 47.75 mmol) was dissolved in 100 mL 1,4-dioxane, and 4-aminobutyl-1-ol (5.1 g, 57.3 mmol) and triethylamine (7.23 g, 71.63 mmol) were added , stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the crude product was added to 100 mL saturated aqueous sodium bicarbonate solution, extracted with dichloromethane (100 mL×2), and the organic phases were combined, washed with water (100 mL×2) and saturated sodium chloride solution ( 100 mL×2), dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the product 4-((4-bromo-2-nitrophenyl)amino)butyl-1-ol 3b (12.8 g, orange-red oil), the product ...
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