Oxindole-naphthofuran derivative, preparation method and application thereof, and pharmaceutical composition and preparation containing oxindole-naphthofuran derivative
A technology of furan derivatives and indole oxides, applied in the directions of drug combination, organic chemistry, antitumor drugs, etc., can solve the problems that have not been recorded, and achieve the effect of good inhibitory effect
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Embodiment 1
[0065] The preparation method of compound 1 (3-(8-methoxy-2-phenylnaphthalene[2,1-b]furan-1-yl)indol-2-one, the chemical structure is as follows):
[0066]
[0067] 3-Hydroxy-3-(2-oxo-2-phenylethyl)indol-2-one (53.4 mg), 7-methoxynaphthalene-2-ol (43.6 mg) and trifluoromethanesulfonic acid ( 3.6 μL) were added together into a sealed reaction tube containing 0.4 mL of toluene solvent, and the reaction was continuously stirred at 80° C. for 14 h. After the reaction is complete, the reaction solution is cooled. The reaction solution was separated and purified by silica gel chromatography, and the eluent was petroleum ether: ethyl acetate = 8:1. After elution, the fraction containing the target compound was collected. Remove the solvent to obtain 3-(8-methoxy-2-phenylnaphthalene[2,1-b]furan-1-yl)indol-2-one, whose nuclear magnetic spectrum is as follows figure 1 As shown, the data is parsed as follows:
[0068] 1 H NMR (400MHz, CDCl 3 )δ9.87(s,1H),7.93–7.90(m,2H),7.73(d,J=...
Embodiment 2
[0071] The preparation method of compound 2 (3-(8-methoxy-2-(o-tolyl)naphthalene[2,1-b]furan-1-yl)indol-2-one, the chemical structure is as follows):
[0072]
[0073] 3-Hydroxy-3-(2-oxo-2-(o-tolyl)ethyl)indol-2-one (56.2mg), 7-methoxynaphthalene-2-ol (48.6mg) and tri Fluoromethanesulfonic acid (5.4 μL) was added together into a sealed reaction tube containing 0.5 mL of toluene solvent, and the reaction was continuously stirred at 75° C. for 16 h. After the reaction is complete, the reaction solution is cooled. The reaction liquid was separated and purified by silica gel chromatography, and the eluent was petroleum ether: ethyl acetate = 7:1. After elution, the fraction containing the target compound was collected. Remove the solvent to obtain 3-(8-methoxy-2-(o-tolyl)naphthalene[2,1-b]furan-1-yl)indol-2-one, whose nuclear magnetic spectrum is as follows figure 2 As shown, the data is parsed as follows:
[0074] 1 H NMR (400MHz, CDCl 3 )δ9.53(s,1H),7.73(d,J=8.8Hz,1H),7...
Embodiment 3
[0077] The preparation method of compound 3 (3-(8-methoxy-2-(m-tolyl)naphthalene[2,1-b]furan-1-yl)indol-2-one, whose chemical structure is as follows:
[0078]
[0079] 3-Hydroxy-3-(2-oxo-2-(m-tolyl)ethyl)indol-2-one (56.2mg), 7-methoxynaphthalene-2-ol (53.2mg) and trifluoro Methanesulfonic acid (7.2 μL) was added together into a sealed reaction tube containing 0.6 mL of toluene solvent, and the reaction was continuously stirred at 90° C. for 13 h. After the reaction is complete, the reaction solution is cooled. The reaction solution was separated and purified by silica gel chromatography, and the eluent was petroleum ether: ethyl acetate = 8:1. After elution, the fraction containing the target compound was collected. Remove the solvent to obtain 3-(8-methoxy-2-(m-tolyl)naphthalene[2,1-b]furan-1-yl)indol-2-one, whose nuclear magnetic spectrum is as follows image 3 As shown, the data is parsed as follows:
[0080] 1 H NMR (400MHz, CDCl 3 )δ9.69(s,1H),7.74–7.72(m,2H),7....
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