A kind of lycorine analog and preparation method thereof
An analog, the technology of lycorine, which is applied in the field of alkali analogs, can solve the problems such as large toxic and side effects of the treatment method, and achieve the effects of protecting the cardiovascular system, mild conditions and inhibiting acetylcholinesterase.
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Embodiment 1
[0044] The preparation method one of lycorine analog 4aa, the steps are as follows:
[0045] ①Add 0.5mmol (102.0mg) of 1-phenyl-3-(trimethylsilyl)prop-2-yn-1-ol, 0.25mmol (36.8mg) of 3,4-dihydro-2(1H )-quinolinone and 0.05 mmol (8.6 mg) of PTSA were dissolved in 10 mL of toluene, and refluxed at 110 ° C for 24 h. After the reaction was completed, the reaction was stopped to generate intermediate 3aa (R 1 = H, R 2 = H).
[0046] ② After the reaction was cooled to room temperature, 0.025 mmol (6.8 mg) of AgOTf was added and reacted at 90°C for 0.5 h. After the reaction was completed, the solvent was removed by suction filtration under reduced pressure, and 35.90 mg of lycorine analogue 4aa was obtained by column chromatography with 1:20 (volume ratio) ethyl acetate / petroleum ether, with a yield of 70%.
[0047] 1 H NMR (500MHz, CDCl 3 )δ7.55–7.48(m, 4H), 7.44–7.37(m, 2H), 7.21(t, J=7.6Hz, 1H), 7.12(d, J=7.3Hz, 1H), 3.29(t, J =7.4Hz, 2H), 3.05(t, J=7.6Hz, 2H), 2.77(s, 3H); ...
Embodiment 2
[0053] The preparation steps of lycorine analog 4bb are as follows:
[0054] ① Add 0.05mmol (5.7mg) trifluoroacetic acid, 0.5mmol (109.1mg) 1-p-tolyl-3-(trimethylsilyl)prop-2-yn-1-ol, 0.25mmol (36.8mg) 3,4-dihydro-2(1H)-quinolinone, add 3mL toluene to dissolve, reflux reaction at 110°C for 24h, stop the reaction after the reaction, and generate intermediate 3bb(R 1 = Me,R 2 = H).
[0055]② After the reaction was cooled to room temperature, 0.025 mmol (6.8 mg) of AgOTf was added and reacted at 90°C for 1 h. After the reaction was completed, the solvent was removed by suction filtration under reduced pressure, and 39.89 mg of lycorine analogue 4bb was obtained by column chromatography with 1:20 (volume ratio) ethyl acetate / petroleum ether, with a yield of 73%.
[0056] 1 H NMR (500MHz, CDCl 3 )δ7.40(d, J=7.9Hz, 3H), 7.33(d, J=7.5Hz, 2H), 7.21(s, 1H), 7.11(d, J=7.2Hz, 1H), 3.29(s, 2H), 3.05(s, 2H), 2.77(d, J=1.1Hz, 3H), 2.46(s, 3H); 13 C NMR (126MHz, CDCl 3 )δ 168.3, 136....
Embodiment 3
[0058] The preparation steps of lycorine analog 4cc are as follows:
[0059] ① Add 0.5mmol (119.0mg) 1-p-chlorophenyl-3-(trimethylsilyl) prop-2-yn-1-alcohol, 0.25mmol (36.8mg) 3,4-dihydro-2( 1H)-quinolinone and 0.05mmol (8.6mg) of PTSA were dissolved in 10mL of chlorobenzene, and refluxed at 130°C for 24h. After the reaction was completed, the reaction was stopped to generate the intermediate 3cc(R 1 = Cl, R 2 = H).
[0060] ② After the reaction was cooled to room temperature, 0.025 mmol (6.8 mg) of AgOTf was added and reacted at 100 °C for 2 h. After the reaction was completed, the solvent was removed by suction filtration under reduced pressure, and lycorine analog 4cc 33.92mg was obtained by column chromatography with ethyl acetate / petroleum ether at 1:20 (volume ratio), with a yield of 61%.
[0061] 1 H NMR (500MHz, CDCl 3 )δ7.52–7.46(m, 2H), 7.45–7.41(m, 2H), 7.36(d, J=7.7Hz, 1H), 7.22(t, J=7.6Hz, 1H), 7.13(dd, J =7.3, 0.7Hz, 1H), 3.29(t, J=7.5Hz, 2H), 3.05(t, J=7.5...
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