Compounds and uses thereof for the treatment of nervous system diseases
A technology for neurological diseases and compounds, which is applied in the field of compounds for the treatment of neurological diseases, can solve problems that cannot meet the expectations of safety and effectiveness, and achieve the best therapeutic effect
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Embodiment 1
[0116] Example 1: 7,8-dihydroxy-2-(4-(piperidin-1-yl)phenyl)-4H-chromen-4-one
[0117] (1;7,8-dihydroxy-2-(4-(piperidin-1-yl)phenyl)-4H-chromen-4-one)
[0118]
[0119] Step (1) Synthesis of 1-(3,4-bis(benzyloxy)-2-hydroxyphenyl)ethanone (1b)
[0120] To a mixture of 1-(2,3,4-trihydroxyphenyl)ethanone (1a, 50.0 g, 297.4 mmol), benzyl bromide (101.7 g, 594.7 mmol) and acetonitrile (1200 mL) was added potassium carbonate ( 82.2g, 594.7mmol), the resulting mixture was stirred at 80°C for 15 hours. After the reaction was completed, cool to room temperature, remove insoluble matter by suction filtration under reduced pressure, and concentrate the obtained filtrate under reduced pressure to obtain a residue. The residue was dissolved in ethanol (1000 mL), heated to 80°C and stirred for 1 hour, cooled to room temperature, a solid precipitated, filtered to obtain a filter cake, and dried under reduced pressure to obtain a yellow solid, which was compound 1-(3,4-di (Benzyloxy)-2-...
Embodiment 2
[0130] Example 2: 7,8-dimethoxy-2-(4-(piperidin-1-yl)phenyl)-4H-chromen-4-one
[0131] (2;7,8-dimethoxy-2-(4-(piperidin-1-yl)phenyl)-4H-chromen-4-one)
[0132]
[0133]
[0134] Step (1) Synthesis of 3-(4-bromophenyl)-1-(2-hydroxy-3,4-dimethoxyphenyl)-prop-2-en-1-one (2b)
[0135] To 1-(2-hydroxy-3,4-dimethoxyphenyl)ethanone (2a, 33.7g, 172.2mmol), 4-bromobenzaldehyde (31.9g, 172.2mmol), ethanol (300mL) and H 2 To the mixture of O (100 mL) was added potassium hydroxide (19.3 g, 344.4 mmol). The resulting mixture was warmed to 80°C and stirred overnight. After the reaction was completed, it was cooled to room temperature, and then adjusted to pH=5 with 1N hydrochloric acid solution, and solids were precipitated. Filter under reduced pressure, collect the filter cake, and dry under reduced pressure to obtain 52.9 g of red solid, which is the crude product 3-(4-bromophenyl)-1-(2-hydroxy-3,4-dimethoxyphenyl )-prop-2-en-1-one (2b). The compound was directly used in the n...
Embodiment 3
[0141] Example 3: 2-(4-(4-(dimethylamino)piperidin-1-yl)phenyl)-7,8-dihydroxy-4H-chromen-4-one
[0142] (3;2-(4-(4-(dimethylamino)piperidin-1-yl)phenyl)-7,8-dihydroxy-4H-chromen-4-one)
[0143]
[0144] Step (1) 7,8-bis(benzyloxy)-2-(4-(4-(dimethylamino)piperidin-1-yl)phenyl)-4H-chromen-4-one (3a) Synthesis
[0145] In the glove box, 7,8-bis(benzyloxy)-2-(4-bromophenyl)-4H-chromen-4-one (1d, 41.0g, 79.9mmol), Xphos (7.4g, 15.6mmol), Pd 2 (dba) 3 (7.15g, 7.8mmol) and cesium carbonate (50.7g, 15.6mmol) were added 1,4-dioxane (400mL) and 4-dimethylaminopiperidine (15.0g, 117mmol). The resulting mixture was warmed to 110°C and stirred for 2.5 hours. After the reaction, the mixture was cooled to room temperature, poured into water (300 mL), added EtOAc (200 mL×3) for extraction, and the organic phase was separated and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chroma...
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