An isospirulin compound with antitumor activity, preparation method and use
A technology for anti-tumor activity and acidic compounds, which is applied in the fields of organic chemical methods, anti-tumor drugs, organic active ingredients, etc., and can solve the problem of few researches on isomeric derivatives of spirulina and few studies on the pharmacological activity of isospirin compounds and other problems, to achieve the effect of cheap starting materials, simple synthesis method and saving production cost
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Embodiment 1
[0042] the preparation of
[0043] The reaction formula is:
[0044]
[0045] The specific steps are: add 0.36mmol ethyl-3-(2-acetyl 5-methoxyphenoxy)acrylate, 0.36mmol 1,2,3,4-tetrahydroisoquinoline, 0.24mmol elemental iodine, 0.3mmol trifluoroacetic acid, 2mL dimethyl sulfoxide, magnetic stirring reaction at 130°C for 10 hours, after the reaction was completed, the reaction solution was extracted, the organic layer was washed, dried, and the solvent was distilled off under reduced pressure. The crude product was obtained, and the crude product was separated and purified by column chromatography using petroleum ether / ethyl acetate=10:1 (V / V) as the eluent to obtain the desired product, which was a white solid with a yield of 74%.
[0046] The identification data result of gained product is: 1 H-NMR (400MHz, CDCl 3 ):δ(ppm)8.30–8.20(m,2H),7.41–7.32(m,2H),7.32–7.28(m,1H),7.03–6.94(m,2H),4.92–4.73(m,2H) ,4.47(q,J=7.2Hz,2H),3.94(s,3H),3.18–3.07(m,2H),1.47(t,J=7.2Hz,3H). ...
Embodiment 2
[0048] the preparation of
[0049] The reaction formula is:
[0050]
[0051] The specific steps are: add 0.36mmol ethyl-3-(2-acetophenoxy)acrylate, 0.36mmol 1,2,3,4-tetrahydro-9H-pyridine[3,4- B] Indole, 0.24mmol elemental iodine, 0.3mmol trifluoroacetic acid, 2mL dimethyl sulfoxide, magnetic stirring reaction at 130°C for 10 hours, after the reaction was completed, the reaction solution was extracted, the organic layer was washed, dried, The solvent was distilled off under reduced pressure to obtain the crude product, and the crude product was separated and purified by column chromatography with petroleum ether / ethyl acetate=8:1 (V / V) as the eluent to obtain the desired product. The product was a white solid, and the yield 70%.
[0052] The identification data result of gained product is: 1 H-NMR (400MHz, CDCl 3 ): δ (ppm) 11.54 (s, 1H), 9.60 (d, J = 7.2Hz, 1H), 8.41 (dd, J = 7.6, 1.6Hz, 1H), 8.01 (dd, J = 8.0, 1.2Hz, 1H),7.72–7.61(m,2H),7.60–7.51(m,1H),7.50–7.39(m,2...
Embodiment 3
[0054] the preparation of
[0055] The reaction formula is:
[0056]
[0057] The specific steps are: add 0.36mmol methyl-3-(2-acetophenoxy)acrylate, 0.36mmol 1,2,3,4-tetrahydroisoquinoline, 0.24mmol elemental iodine, 0.3mmol trifluoroacetic acid, 2mL dimethyl sulfoxide, magnetic stirring reaction at 130°C for 10 hours, after the reaction was completed, the reaction solution was extracted, the organic layer was washed, dried, and the solvent was distilled off under reduced pressure to obtain the crude product, the crude product Using petroleum ether / ethyl acetate=15:1 (V / V) as the eluent, the desired product was obtained by column chromatography separation and purification. The product was a white solid with a yield of 85%.
[0058] The identification data result of gained product is: 1 H-NMR (400MHz, CDCl 3 ): δ(ppm)8.41–8.20(m,2H),7.68–7.62(m,1H),7.61–7.56(m,1H),7.41–7.37(m,1H),7.37–7.34(m,2H) ,7.31–7.26(m,1H),4.85–4.77(m,2H),3.98(s,3H),3.10(t,J=6.8Hz,2H). 13 C-NMR...
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