A Chrysin Leucine Derivative with EGFR Kinase Inhibitory Activity
A leucine methyl ester and drug technology, applied in organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of undisclosed and undisclosed EGFR tyrosine kinase targeted inhibition
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Embodiment 1
[0037] N- [2-(5-Hydroxy-2-phenyl- 4H -Benzopyrone-7-O)octanoyl]-L-leucine methyl ester (Compound I)
[0038]
[0039] Step 1: Add anhydrous potassium carbonate (2073.2 mg) to a solution of chrysin (2524.4 mg) in acetone (100 mL) with stirring. Stir at 60°C for 30 min. Ethyl 2-bromooctanoate (2724 μL) and the catalyst potassium iodide (166.0 mg) were slowly added dropwise with a constant pressure dropping funnel, and the mixture was stirred and refluxed at 60°C. After the reaction was detected by TLC, it was cooled, filtered, and the filter residue was washed with a small amount of acetone, and the organic solvent was removed from the obtained filtrate on a rotary evaporator. After separation and purification by silica gel column chromatography (dichloromethane / acetone=50:1), compound 3 was obtained. Yield: 60%. m.p.100-103°C. 1 H NMR (500 MHz, CDCl 3 ) δ 12.69 (d, J = 22.9 Hz, 1H), 7.85 (t, J = 10.7 Hz, 2H),7.62 – 7.41 (m, 3H), 6.66 (s, 1H), 6.47 (d, J = 1.9 Hz...
Embodiment 2
[0046] Example 2 In vitro activity test
[0047] The cell lines are MCF-7 (human breast cancer cells) and HVECs (human normal vascular endothelial cells).
[0048] The culture medium is DMEM+10% FBS+ 5 mL double antibody
[0049] Sample solution preparation: After dissolving with DMSO (Merck), the concentration is 33333.33 μmol / L
[0050] 1. Seed the plate Add the cell suspension to a 96-well plate, 100 μL per well (the cell content in each well is about 8000 cells / well), store at 37°C, 5% CO 2 Cultivate in the incubator for 24 h;
[0051] 2. Add drug-use medium to prepare the gradient concentration of the sample solution (256, 128, 64, 32, 16, 8, 4, 2 μmol / L), discard the original medium on the 96-well plate, and add different concentrations of drugs to culture base, 100 μL per well, and 5 auxiliary wells for each concentration. For the remaining wells, use the medium containing 3‰ DMSO as a control, and incubate in a 5% incubator at 37°C for 48 h;
[0052] 3. MTT method...
Embodiment 3
[0055] Example 3 Effects of compounds on colony formation and migration of cancer cells MCF-7 (human breast cancer cells) was selected as the cell line
[0056] 1. Mark the culture plate on the back of the 6-well plate with a marker, and use a ruler to draw a line along the diameter of the well to divide each well into 2 parts.
[0057] 2. Add a certain amount of cells to the wells, because different cells grow at different speeds, and the amount of cells taken is also different. The principle of inoculation is that the cells in the wells are basically covered with no obvious gaps after overnight.
[0058] 3. Cell streaking Use a 200 μL sterile tip perpendicular to the cell plane, and scratch the cell layer along the ruler.
[0059] 4. Wash the cells with PBS and take pictures to observe the scratches. After the scratches are completed, wash the cells with PBS 3 times to wash away the non-adherent cells, that is, the cells that were streaked when streaking. Make the gaps lef...
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