A kind of β-lapachone derivative and its preparation method and medical application
A technology of derivatives and compounds, applied in the field of β-lapachone derivatives, to achieve the effect of novel structure, simple operation and good selectivity
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Embodiment 1
[0020] Synthesis of Example 1 Compound
[0021] Under argon protection, the compound 4-amino-3-(aminoethyl)naphthalene-1-phenol (940 mg, 5.0 mmol) was dissolved in 20 mL of dichloromethane, and the solution was cooled to 0 in an ice bath. ℃. A solution of thiocarbonyldiimidazole (978 mg, 5.5 mmol) dissolved in 20 mL of dichloromethane was added dropwise within 10 minutes. After the addition was completed, the temperature was raised to room temperature and reacted for 5 hours. After the completion of the reaction, the solvent was evaporated and washed with a small amount of ethanol to obtain the corresponding light yellow solid. Add 20mL of acetone to dissolve, and cool the solution to 0°C in an ice bath. Will be dissolved in 200 mL of 0.06 M NaH 2 PO 4 3.34 g of Fermi salt was added dropwise to the reaction solution, the temperature was controlled below 10 ℃ to react for 2 hours, filtered and washed with water to obtain 538 mg of orange-yellow red solid I, with a yield of 32%. ...
Embodiment 2
[0023] Example 2 In vitro anti-tumor activity test
[0024] The MTT method was used to test the anti-tumor activity of the target compound. Human liver cancer cell HepG2 was used as the test cell line. Adherent tumor cells in logarithmic growth phase were selected, and after trypsinization, they were prepared into a cell suspension of 5000 cells / mL with RPMI 1640 medium containing 10% calf serum. Inoculate in 96-well culture plate, inoculate 200 μL per well, 37 ℃, 5% CO 2 Cultivate for 24 hours. Set up a negative control group, a positive control group and a drug-administered group. The experimental group was replaced with a new medium containing different concentrations of the tested samples, the control group was replaced with a medium containing an equal volume of solvent, and the positive control group was given the positive control drug adriamycin (diluted with complete medium to a concentration of 10 μmol·L) - 1 ), each group has 3-5 parallel holes, 37 ℃, 5% CO 2 Cultiva...
Embodiment 3
[0025] Example 3 NQO1 activity test
[0026] The 1 mL reaction system contains 25 mM Tris / HCl (pH 7.4), 0.7 mg / mL bovine serum albumin, 0.1% Tween-20, 200 μM NADH, 77 μM Cytochrome c, 2 μg recombinant human NQOl and 1, 2 ,3,4-Tetrahydro-2-thiobenzo[ h ] Quinazoline-5,6-dione (25 μM ). Set the detection wavelength to 550nnm, add NADH to start the reaction at room temperature, calculate the reduction rate from the initial linear part of the reaction curve, and convert it by the molar absorption coefficient of cytochrome c (21.1 mM -1 cm -1 ), the result is expressed as μmol reduced cytochrome c / min / mg NQOl. The ability of the compound to produce reactive oxygen can be judged from the change in the amount of cytochrome c. The rate of reactive oxygen production at the enzyme level of the compound is 1143±62 μmol reduced cytochrome c / min / mg NQOl.
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