Application of dimethylamine derivatives of cleistanone cleistanone in the preparation of anti-heart failure drugs
A kind of technology of cleusenone and its derivatives, which is applied in the direction of drug combination, medical preparations containing active ingredients, pharmaceutical formulas, etc., to achieve good anti-heart failure effect
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Embodiment 1
[0017] Preparation of Example 1 Compound Cleistanone
[0018] The preparation method of compound Cleistanone (I) refers to the method published by VanTrinhThiThanh et al. (VanTrinhThiThanh et al., 2011.Cleistanone:ATriterpenoidfromCleistanthusindochinensiswithaNewCarbonSkeleton.Volume2011, Issue22, pages4108-4111, August2011).
[0019]
Embodiment 2
[0020] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2
[0021] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine three times successively, then dried with anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).
[0022] 1H NMR ...
Embodiment 3
[0026] Example 3 Synthesis of O-(dimethylamino)ethyl derivatives (III) of cleistanone Cleistanone
[0027] Compound II (273mg, 0.5mmol) was dissolved in 20mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and dimethylamine (900mg, 20mmol) were added thereto, and the mixture was heated to reflux for 16h . After the reaction was completed, the reaction solution was poured into ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the light yellow concentrated elution band was collected to obtain compound III as a light yellow solid (160.7 mg, ...
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