Metal organic iridium complex with anticancer activity as well as preparation method and application of metal organic iridium complex
A technology of iridium complex and anti-cancer activity, which is applied in the field of chemical pharmaceuticals and can solve the problems of restricting the curative effect of platinum-based drugs, acquired drug resistance, toxic and side effects, etc.
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Embodiment 1
[0040] Weigh 1.0 g of iridium trichloride hydrate and place it in a 100 mL Schlenk bottle, seal it, vacuumize and fill it with nitrogen for 3 times, and inject 1 . 1 g of 2-phenylpyridine, then inject 30mL of a mixture of ethylene glycol monoethyl ether and deionized water (3:1, v / v), heat and reflux at 110 °C for 24 h, filter, and filter the cake with ethanol and acetone respectively After washing three times each, the obtained light yellow solid powder was dissolved in a small amount of dichloromethane, and purified by adding diethyl ether to obtain a yellow iridium dimer (Ⅴ) product with a yield of 68%.
Embodiment 2
[0042] Put 50.0 mg of iridium dimer (Ⅴ) and 16 mg of potassium isopropylxanthate ligand L1 in a 100 mL Schlenk bottle, vacuum and blow nitrogen, inject 40 mL of methanol as a solvent, and stir at room temperature for 24 h, after the spot plate detection reaction, the solvent was distilled off under reduced pressure, dissolved in a small amount of dichloromethane, filtered, and diffused by adding n-hexane to obtain 42 mg of the target product (I) as light yellow crystals (yield 70%).
[0043] Characterization spectra such as Figure 1 ~ Figure 2 Shown: 1 H NMR (500 MHz, DMSO) δ 9.26 – 9.17 (m, 2H), 8.20 (d, J = 7.9 Hz, 2H), 8.06 – 7.93 (m, 2H), 7.76 (d, J = 7.0 Hz, 2H), 7.49(ddd, J = 7.3, 5.9, 1.4 Hz, 2H), 6.84 – 6.75 (m, 2H), 6.67 (td, J = 7.5, 1.2Hz, 2H), 6.18 – 6.10 (m, 2H), 5.44 (dt, J = 12.3, 6.1 Hz, 1H), 1.43 (d, J =6.1 Hz, 3H), 1.34 (t, J= 9.6 Hz, 3H): theoretical value: 636.10, actually measured 638.7, [M+H] + ;
Embodiment 3
[0045] Put 50.0 mg of iridium dimer (Ⅴ) and 14.9 mg of potassium ethyl xanthate ligand L2 in a 100 mL Schlenk bottle, vacuum and nitrogen, inject 40 mL of methanol as a solvent, and stir at room temperature for 24 h, after spot plate detection, the solvent was distilled off under reduced pressure, dissolved with a small amount of dichloromethane, filtered, and diffused by adding n-hexane to obtain 40.3 mg of the target product (II) as pale yellow crystals (68% yield).
[0046] Characterization spectra such as Figure 3 ~ Figure 4 Shown: 1 H NMR (500 MHz, DMSO) δ 9.21 (dd, J = 5.8,0.8 Hz, 2H), 8.20 (d, J = 8.0 Hz, 2H), 8.01 – 7.94 (m, 2H), 7.79 – 7.69 (m,2H), 7.48 (ddd, J = 7.3, 5.9, 1.3 Hz, 2H), 6.88 – 6.74 (m, 2H), 6.67 (td, J =7.5, 1.2 Hz, 2H), 6.16 (dd, J = 7.6, 0.7 Hz, 2H), 4.67 – 4.44 (m, 2H), 1.38(t, J = 7.1 Hz, 3H). Theoretical value is 622.07, the actual measured value is 645.2, [M+Na] + ;
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