Application of composition of Virosaine A tetrahydropyrrole and morpholinyl derivatives in drugs for resisting chronic obstructive pulmonary disease
A chronic obstructive, compositional technology
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Embodiment 1
[0012] The preparation of embodiment 1 compound Virosaine A
[0013] The preparation method of compound Virosaine A (I) refers to the literature published by Bing-Xin Zhao et al. (Bing-Xin Zhao et al., 2012.Virosaines A and B, Two New Birdcage-Shaped Securinega Alkaloids with an Unprecedented Skeleton from Flueggea virosa.Organic Letters 14(2012) 3096–3099).
[0014]
Embodiment 2
[0015] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Virosaine A
[0016] Compound I (235 mg, 1.00 mmol) was dissolved in 20 mL of benzene, tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 5 mL of 50% sodium hydroxide solution. The mixture was stirred at 35 °C for 8 h. After 8 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=100:1.0, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a brown powder of Compound II (261mg, 78%) .
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Embodiment 3
[0021] Example 3 Synthesis of O-(tetrahydropyrrolyl) ethyl derivatives (III) of Virosaine A
[0022] Compound II (171 mg, 0.5 mmol) was dissolved in 15 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and pyrrolidine (1420 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 1 h. After the reaction, the reaction solution was poured into ice water, extracted twice 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=100:1.5, v / v), and the light yellow concentrated elution band was collected to obtain the O-(tetrahydropyrrolyl)ethyl derivative of VirosaineA (III) Pa...
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