Veraveratramine compounds as well as preparation method and application thereof
A technology of veratramine and compounds, applied in the field of veratramine compounds, can solve the problem of single drug, achieve good market prospects, and strongly inhibit the proliferation of tumor cells
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Embodiment 1
[0190]
[0191] Dissolve the weighed veratramine (3g, 7.33mmol) in 50ml of water, add HCHO (893μl, 8.80mmol) and HCOOH (1372μl, 36.67mmol), and react at reflux at 100°C for 12h under the protection of argon, monitored by TLC After the reaction was completed, it was quenched by adding saturated NaOH solution, extracted with DCM (20ml×3), anhydrous NaOH 2 SO 4 The crude product was dried, filtered and concentrated to obtain a crude product, which was purified by silica gel column chromatography (PE / EA=3:1-1:1) to obtain VT-1 (2.3 g, 74%) as a white solid.
[0192] 1 H NMR (500MHz, CDCl3) δ7.25 (d, J = 6.3Hz, 1H), 7.02 (d, J = 7.7Hz, 1H), 5.48 (brd, J = 5.1Hz, 1H), 3.87–3.82 (m ,1H),3.73–3.67(m,1H),3.61–3.53(m,1H),2.97–2.91(m,1H),2.77(dd,J=15.0,7.5Hz,2H),2.66–2.53(m ,2H),2.47(s,3H),2.41(dd,J=12.9,4.3Hz,1H),2.33(s,3H),2.29–2.24(m,1H),2.16(d,J=7.0Hz, 1H),2.04–1.97(m,1H),1.91–1.70(m,8H),1.65–1.58(m,1H),1.42(d,J=7.2Hz,3H),1.34–1.22(m,2H) ,1.13(s,3H),0.85(d,J=6.5Hz,3H); 13 C ...
Embodiment 2
[0194]
[0195] Veratramine (1g, 2.44mmol) was dissolved in acetone, adding K 2 CO 3 (3.4g, 24.45mmol) and diethyl sulfate (1.9g, 12.2mmol) were refluxed at 56°C for 12h. After the completion of the reaction monitored by TLC, add ammonia and stir for 1 h to quench, concentrate under reduced pressure to remove most of the solvent, wash with water and extract with DCM (5ml×3), combine the organic phases, anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, the crude product was purified by silica gel column chromatography (PE / EA=3:1-1:1), and the obtained white solid was VT-2 (836 mg, 78%).
[0196] 1 H NMR (500MHz, CDCl 3 )δ7.25(d, J=8.6Hz,1H),7.02(d,J=7.7Hz,1H),5.48(brd,J=5.2Hz,1H),3.83(s,1H),3.69–3.62( m,1H),3.61–3.53(m,1H),2.98–2.88(m,2H),2.84(d,J=10.9Hz,1H),2.77(dd,J=15.0,7.4Hz,1H),2.65 –2.52(m,3H),2.49–2.44(m,1H),2.41(ddd,J=13.0,4.7,1.9Hz,1H),2.33(s,3H),2.31–2.23(m,1H),2.04 –1.96(m,1H),1.92–1.76(m,5H),1.73–1.55(m,5H),1.38(d,J=7.1Hz,3H),1.25–...
Embodiment 3
[0198]
[0199] Veratramine is used as the raw material, the allyl reagent is 3-bromopropene, and the synthesis method is the same as that of VT-2
[0200] White solid, about 89% yield. 1 H NMR (500MHz, CDCl 3 )δ7.25(d, J=7.8Hz,1H),7.01(d,J=7.7Hz,1H),5.96(m,1H),5.48(brd,J=5.2Hz,1H),5.26–5.16( m,2H),3.81–3.86(m,1H),3.74–3.65(m,1H),3.61–3.51(m,2H),3.04(dd,J=14.4,7.7Hz,1H),2.95(td, J=11.6, 5.3Hz, 1H), 2.86(d, J=10.9Hz, 1H), 2.76(dd, J=14.9, 7.4Hz, 1H), 2.66–2.53(m, 2H), 2.50–2.34(m ,2H),2.31(s,3H),2.29–2.22(m,1H),2.04–1.96(m,1H),1.93–1.76(m,7H),1.68–1.54(m,2H),1.40(d ,J=7.1Hz,3H),1.30–1.25(m,1H),1.13(s,3H),0.87(d,J=6.7Hz,3H); 13 C NMR (125MHz, CDCl 3 )δ145.01,144.07,142.61,140.98,135.74,132.68,124.04,121.96,120.77,117.41,71.84,67.50,67.42,59.75,57.09,56.23,41.96,41.30,41.27,38.12,36.99,34.21,31.37,30.47,30.43 ,28.24,19.52,19.32,16.17,13.91.HRMS(ESI):m / z calcd for C 30 h 44 NO 2 + [M+H] + :450.3367,found(450.3369).
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