A class of cyclometalated iridium(III) cationic and zwitterionic complexes with anticancer activity, their preparation methods and applications

Abstract

The present invention discloses a class of cyclometalated iridium(III) cationic and zwitterionic complexes with anticancer activity, and their preparation methods and applications. The structural formulas of the complexes are shown in Formula (I) and (II), which are one of the structural formulas. Among them, the ligand reacts with cycloiridium under reaction conditions to obtain the cyclometalated iridium(III) zwitterionic complex (I) and the cationic complex (II). The method for synthesizing the novel cyclometalated iridium(III) complex provided by the present invention has good substrate generality, high yield, and easy separation. The obtained complexes show very good anticancer activity, and the anticancer activity of the cationic complex (II) is better than that of the zwitterionic complex (I), having potential application prospects in biomedicine.

Description

Technical Field:

[0001] The present invention relates to metal complexes, specifically a class of cyclometalated iridium(III) cationic and zwitterionic complexes with anticancer activity, their preparation methods and applications, and belongs to the field of chemical pharmaceuticals. Background Art:

[0002] Cancer is the result of long-term accumulation of gene damage and alteration under the long-term action of external factors on human cells, and is a multi-factor, multi-stage, complex and progressive process. Despite significant progress in the past five decades, cancer remains one of the main causes of death worldwide. Surgical resection, radiotherapy, and chemotherapy are still the main strategies for cancer treatment. Chemotherapy is a means of systemic treatment that enables chemical drugs to act on cancer cells and kill them. Currently, cisplatin is mainly used as a first-line drug for cancer treatment, but its severe side effects have led scientists to strive to find more effective and less toxic new metal-based anticancer drugs. Among them, the research on platinum group metals such as iridium, rhodium, and ruthenium is particularly prominent. Over the past many years, metal iridium complexes have become imaging probes and potential anticancer drugs due to their structural diversity and different mechanisms of action. Among these complexes, cyclometalated iridium(III) complexes have been widely studied due to their rich luminescent properties and good cell permeability, and have a wide range of applications in therapeutic drugs, cell imaging, or biological probes. In the cyclometalated iridium(III) complex (Formula A), the metal center is closely surrounded by three groups of bidentate chelating ligands to form a six-coordinate mode. Here, a class of cyclometalated iridium(III) cationic and zwitterionic complexes with anticancer activity, their preparation methods and applications are introduced. In the cyclometalated iridium(III) cationic complex (Formula B1), the [N,N] chelating ligand is a neutral ligand (zero valence), and both groups of [C,N] chelating ligands are -1 valence, and the metal center iridium is +3 valence, so the overall is +1 valence, and the outside has an anion (C6H4)CH3SO3 - as a counterion. In the cyclometalated iridium(III) zwitterionic complex (Formula B2), the [N,N] chelating ligand is -1 valence because it has an anionic group SO3 - and both groups of [C,N] chelating ligands are -1 valence, and the metal center iridium is +3 valence, so the overall is zero valence, and there is no counterion outside. Through research, it is found that the cytotoxic activities of cationic and zwitterionic complexes against cancer cells show significant differences.

[0003] Summary of the Invention:

[0004] The present invention provides a class of cyclometalated iridium(III) cationic and zwitterionic complexes with anti-cancer activity, their preparation methods and applications, and hopes to obtain a series of cyclometalated iridium(III) complexes with good anti-tumor effects. Such cyclometalated iridium(III) complexes all exhibit excellent anti-tumor effects.

[0005] The molecular structural formula of the cyclometalated iridium(III) complex is:

[0006]

[0007] In the formula, R1 is one of and R2 is hydrogen, a C1-C 15 alkyl group, a halogen, or a halogenated C1-C 15 alkyl group; is one of and X is Cl - , PF6 - , BF4 - , BPh4 - , SbF6 - , one of them.

[0008] For the cyclometalated iridium(III) complex of the present invention, in formula (I), R1 is R2 is isopropyl, is The specific structural formula is as shown in formula 1; in formula (I), R1 is R2 is isopropyl, is The specific structural formula is as shown in formula 2; in formula (I), R1 is R2 is isopropyl, is The specific structural formula is as shown in formula 3; in formula (I), R1 is R2 is isopropyl, is The specific structural formula is as shown in formula 4; in formula (I), R1 is R2 is isopropyl, is The specific structural formula is as shown in formula 5; in formula (I), R1 is R2 is isopropyl, is The specific structural formula is as shown in formula 6; in formula (II), R1 is R2 is isopropyl, is X is The specific structural formula is as shown in formula 7; in formula (II), R1 is R2 is isopropyl, is X is The specific structural formula is as shown in Formula 8; in Formula (II), R1 is R2 is isopropyl, is X is The specific structural formula is as shown in Formula 9; in Formula (II), R1 is R2 is isopropyl, is X is The specific structural formula is as shown in Formula 10; in Formula (II), R1 is R2 is isopropyl, is X is The specific structural formula is as shown in Formula 11; in Formula (II), R1 is R2 is isopropyl, is X is The specific structural formula is as shown in Formula 12;

[0009]

[0010] The preparation method of the cyclometalated iridium(III) complex of the present invention comprises the following steps: under nitrogen protection, reacting the dimer shown in Formula (V) and the ligand shown in Formula (III) in methanol as the solvent at room temperature for 24 h to obtain Formula (I); under nitrogen protection, reacting the dimer shown in Formula (V) and the ligand shown in Formula (IV) in methanol as the solvent at room temperature for 24 h, then adding AX and continuing the reaction for 12 h to obtain Formula (II); the inorganic salt AX is one of NaX, KX, and NH4X; the specific synthetic route is:

[0011] When the complex is 1, it is prepared by the following method:

[0012] Under nitrogen protection, add 46.2 mg of the cycloiridium dimer of Formula (V) to a 100 mL Schlenk flask 32.0 mg of the ligand of Formula (III) ( R2 = isopropyl) and 20 mL of anhydrous methanol, react at room temperature for 24 h. After the reaction is completed, the solution is dried by rotary evaporation, dissolved in a small amount of dichloromethane, then an excessive amount of poor solvent n-hexane is added, precipitation occurs, the precipitate is filtered through a sintered filter and washed with n-hexane, and dried in vacuo to obtain a brown solid 1;

[0013] When the complex is 2, it is prepared by the following method:

[0014] Under nitrogen protection, 36.6 mg of the cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask. 22.8 mg of the ligand of formula (III) ( R2 = isopropyl) and 20 mL of anhydrous methanol were added, and the reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was evaporated to dryness with a rotary evaporator, dissolved in a small amount of dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a red solid 2.

[0015] When the complex is 3, it is prepared by the following method:

[0016] Under nitrogen protection, 33.8 mg of the cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask. 22.3 mg of the ligand of formula (III) ( R2 = isopropyl) and 20 mL of anhydrous methanol were added, and the reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was evaporated to dryness with a rotary evaporator, dissolved in a small amount of dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a red solid 3.

[0017] When the complex is 4, it is prepared by the following method:

[0018] Under nitrogen protection, 45.4 mg of the cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask. 31.5 mg of the ligand of formula (III) ( R2 = isopropyl) and 20 mL of anhydrous methanol were added, and the reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was evaporated to dryness with a rotary evaporator, dissolved in a small amount of dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a yellow solid 4.

[0019] When the complex is 5, it is prepared by the following method:

[0020] Under nitrogen protection, 36.6 mg of the cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask. 22.8 mg of the ligand of formula (III) ( R2 = isopropyl) and 20 mL of anhydrous methanol were added, and the reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was evaporated to dryness with a rotary evaporator, dissolved in a small amount of dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a yellow solid 5.

[0021] When the complex is 6, it is prepared by the following method:

[0022] Under nitrogen protection, add 33.8 mg of the cycloiridium dimer of formula (V) 22.3 mg of the ligand of formula (III) ( R2 = isopropyl) and 20 mL of anhydrous methanol, react at room temperature for 24 h. After the reaction is completed, the solution is dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane is added. A precipitate appears. The precipitate is filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a red solid 6;

[0023] When the complex is 7, it is prepared by the following method:

[0024] Under nitrogen protection, add 53.7 mg of the cycloiridium dimer of formula (V) 27.0 mg of the ligand of formula (IV) ( R2 = isopropyl) and 20 mL of anhydrous methanol, react at room temperature for 24 h, and then add 19.4 mg of sodium p-toluenesulfonate Stir for 12 h. After the reaction is completed, the solution is dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane is added. A precipitate appears. The precipitate is filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a brown solid 7;

[0025] When the complex is 8, it is prepared by the following method:

[0026] Under nitrogen protection, add 48.6 mg of the cycloiridium dimer of formula (V) 22.0 mg of the ligand of formula (IV) ( R2 = isopropyl) and 20 mL of anhydrous methanol, react at room temperature for 24 h, and then add 15.8 mg of sodium p-toluenesulfonate and stir for 12 h. After the reaction is completed, the solution is dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane is added. A precipitate appears. The precipitate is filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a brown solid 8;

[0027] When the complex is 9, it is prepared by the following method:

[0028] Under nitrogen protection, add 43.8 mg of the cycloiridium dimer of formula (V) 22.0 mg of the ligand of formula (IV) ( R2 = isopropyl), and 20 mL of anhydrous methanol. After reacting at room temperature for 24 h, 15.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 9 mg of a red solid;

[0029] When the complex is 10, it is prepared by the following method:

[0030] Under nitrogen protection, 43.8 mg of cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask 22.0 mg of ligand of formula (IV) ( R2 = isopropyl), and 20 mL of anhydrous methanol. After reacting at room temperature for 24 h, 15.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 10 mg of a brown solid;

[0031] When the complex is 11, it is prepared by the following method:

[0032] Under nitrogen protection, 35.8 mg of cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask 20.0 mg of ligand of formula (IV) ( R2 = isopropyl), and 20 mL of anhydrous methanol. After reacting at room temperature for 24 h, 11.7 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 11 mg of a brown solid;

[0033] When the complex is 12, it is prepared by the following method:

[0034] Under nitrogen protection, 31.6 mg of cycloiridium dimer of formula (V) was added to a 100 mL Schlenk flask 21.0 mg of ligand of formula (IV) ( R2 = isopropyl), and 20 mL of anhydrous methanol. After reacting at room temperature for 24 h, 10.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 12 mg of a yellow solid.

[0035] Beneficial effects:

[0036] (1) The present invention provides a class of cyclometalated iridium(III) cationic and zwitterionic complexes, their preparation methods and applications, with high synthesis efficiency, and the prepared complexes have broad application prospects in biomedicine.

[0037] (2) The present invention compares the anticancer activities of zwitterionic iridium(III) complexes and cationic iridium(III) complexes, providing a new research idea for the subsequent synthesis research of drug ligands. Description of the drawings:

[0038] Figure 1 1H NMR spectrum of Complex 1 of the present invention.

[0039] Figure 2 Mass spectrum of Complex 1 of the present invention.

[0040] Figure 3 1H NMR spectrum of Complex 2 of the present invention.

[0041] Figure 4 Mass spectrum of Complex 2 of the present invention.

[0042] Figure 5 Single crystal structure of Complex 2 of the present invention

[0043] Figure 6 1H NMR spectrum of Complex 3 of the present invention

[0044] Figure 7 Mass spectrum of Complex 3 of the present invention.

[0045] Figure 8 1H NMR spectrum of Complex 4 of the present invention

[0046] Figure 9 Mass spectrum of Complex 4 of the present invention.

[0047] Figure 10 1H NMR spectrum of Complex 5 of the present invention

[0048] Figure 11 Mass spectrum of Complex 5 of the present invention.

[0049] Figure 12 1H NMR spectrum of Complex 6 of the present invention.

[0050] Figure 13 Mass spectrum of Complex 6 of the present invention.

[0051] Figure 14 1H NMR spectrum of Complex 7 of the present invention.

[0052] Figure 15 Mass spectrum of Complex 7 of the present invention.

[0053] Figure 16 1H NMR spectrum of complex 8 of the present invention

[0054] Figure 17 Mass spectrum of complex 8 of the present invention

[0055] Figure 18 1H NMR spectrum of complex 9 of the present invention

[0056] Figure 19 Mass spectrum of complex 9 of the present invention

[0057] Figure 20 1H NMR spectrum of complex 10 of the present invention

[0058] Figure 21 Mass spectrum of complex 10 of the present invention

[0059] Figure 22 1H NMR spectrum of complex 11 of the present invention

[0060] Figure 23 Mass spectrum of complex 11 of the present invention

[0061] Figure 24 1H NMR spectrum of complex 12 of the present invention

[0062] Figure 25 Mass spectrum of complex 12 of the present invention Detailed implementation method:

[0063] The following is a detailed description of the embodiments of the present invention. The embodiments are implemented on the premise of the technical solution of the present invention, and detailed implementation methods and specific operation processes are given. However, the protection scope of the present invention is not limited to the following embodiments.

[0064] Example 1

[0065] When the complex is 1, it is prepared by the following method:

[0066] Under nitrogen protection, 46.2 mg of cycloiridium dimer (Formula (V) ), 32.0 mg of ligand (Formula (III), R2 = isopropyl) and 20 mL of anhydrous methanol are added to a 100 mL Schlenk flask, and the reaction is carried out at room temperature for 24 h. After the reaction is completed, the solution is dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane is added. A precipitate appears. The precipitate is filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 51.4 mg of brown solid 1 with a yield of 70%.

[0067] The NMR characterization is 11H NMR (500 MHz, DMSO) δ 9.24 (s, 1H, CH=N), 8.22 (s, 1H), 8.00 (d, J = 8.1 Hz, 2H), 7.94 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 7.7 Hz, 1H), 7.75 (s, 1H), 7.49 (d, J = 6.5 Hz, 1H), 7.40 (s, 1H), 7.33 (s, 1H), 7.20 (s, 1H), 7.11 (s, 1H), 6.86 (t, J = 7.5 Hz, 2H), 6.71 (s, 1H), 6.68 (d, J = 3.6 Hz, 1H), 6.67 (s, 1H), 6.66 (s, 1H), 6.12 (s, 1H), 5.66 (d, J = 7.7 Hz, 2H), 4.14 (s, 3H, NCH3), 2.09 (m, 2H, CH(CH3)2)), 1.19 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 1.06 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.82 (d, J = 6.4 Hz, 3H, CH(CH3)2)), 0.23 (d, J = 6.6 Hz, 3H, CH(CH3)2).

[0068] Mass spectrometry: C 39 H 39 Theoretical value of IrN5O3S is 850.24083, actually measured value is 850.23761, [M + H] + .

[0069] Elemental analysis. Theoretical value: C 39 H 38 For IrN5O3S: C, 55.17; H, 4.51; N, 8.25. Actually measured: C, 55.32; H, 4.48; N, 8.05.

[0070] Example 2

[0071] When the complex is 2, it is prepared by the following method:

[0072] Under nitrogen protection, 36.6 mg of cycloiridium dimer (Formula (V) ) and 22.8 mg of ligand (Formula (III), R2 = isopropyl), and 20 mL of anhydrous methanol were added, and the reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was evaporated to dryness with a rotary evaporator, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane was added. A precipitate appeared, and the precipitate was filtered with a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain 33.2 mg of red solid 2 with a yield of 59%. A small amount of the product was taken, dissolved in dichloromethane in a vial, and then n-hexane was slowly added along the wall of the vial to grow its single crystal by diffusion;

[0073] Characterized by NMR as 1 1H NMR (500 MHz, DMSO) δ 9.24 (s, 1H, CH=N), 8.16–8.11 (m, 2H), 8.09 (d, J = 8.3 Hz, 1H), 7.94 (t, J = 8.3 Hz, 1H), 7.86 (d, J = 4.0 Hz, 2H), 7.76 (s, 1H), 7.75 (s, 1H), 7.46 (d, J = 8.6 Hz, 1H), 7.28 (t, J = 7.1 Hz, 1H), 7.22 (d, J = 5.6 Hz, 1H), 7.20 (s, 1H), 7.13 (s, 1H), 6.73 (s, 1H), 6.50 (d, 1H), 6.33 (d, J = 8.6 Hz, 1H), 5.56 (d, J = 2.4 Hz, 1H), 5.12 (d, J = 2.5 Hz, 1H), 4.14 (s, 3H, NCH3), 3.48 (s, 3H, OCH3), 3.44 (s, 3H, OCH3), 2.15–2.02 (m, 2H, CH(CH3)2)), 1.18 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 1.07 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.80 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.24 (d, J = 6.5 Hz, 3H, CH(CH3)2).

[0074] Mass spectrometry: C 41 H 43 The theoretical value of IrN5O5S is 910.26205, and the actually measured value is 910.26022, [M + H] + .

[0075] Elemental analysis. Theoretical values: C 41 H 42 IrN5O5S: C, 54.17; H, 4.66; N, 7.70. The actually measured values: C, 54.30; H, 4.48; N, 7.55.

[0076] Example 3

[0077] When the complex is 3, it is prepared by the following method:

[0078] Under nitrogen protection, 33.8 mg of the cycloiridium dimer (Formula (V) ), 22.3 mg of the ligand (Formula (III), R2 = isopropyl) and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask and reacted at room temperature for 24 h. After the reaction, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 35.6 mg of a red solid 3 with a yield of 67%.

[0079] Characterized by NMR as 1 H NMR (500 MHz, DMSO) δ 9.23 (s, 1H, CH=N), 8.18 (m, 3H), 7.98 (d, J = 8.0 Hz, 1H), 7.96 (s, 1H), 7.93–7.86 (m, 2H), 7.73 (s, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.38 (d, J = 8.0 Hz, 1H), 7.34 (d, J = 6.1 Hz, 1H), 7.29 (t, J = 7.2 Hz, 1H), 7.20 (s, 1H), 7.10 (s, 1H), 6.69 (d, J = 8.4 Hz, 1H), 6.66 (s, 1H), 6.52 (d, J = 7.8 Hz, 1H), 5.92 (s, 1H), 5.44 (s, 1H), 4.13 (s, 3H, NCH3), 2.10–1.99 (m, 2H, CH(CH3)2)), 1.95 (s, 3H, CH3)), 1.93 (s, 3H, CH3), 1.19 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.07 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.80 (d, J = 6.4 Hz, 3H, CH(CH3)2)), 0.23 (d, J = 6.5 Hz, 3H, CH(CH3)2)).

[0080] Mass spectrometry: C 41 H 43 The theoretical value of IrN5O3S is 878.27211, and the actual measured value is 878.70463, [M+H] + .

[0081] Elemental analysis. Theoretical values: C 41 H 42 IrN5O3S: C, 56.15; H, 4.83; N, 7.98. The actual measured values: C, 56.30; H, 4.75; N, 7.85.

[0082] Example 4

[0083] When the complex is 4, it is prepared by the following method:

[0084] Under nitrogen protection, 45.4 mg of cycloiridium dimer (Formula (V) ), 31.5 mg of ligand (Formula (III), R2 = isopropyl), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask and reacted at room temperature for 24 h. After the reaction, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 48.6 mg of yellow solid 4 with a yield of 67%.

[0085] Characterized by NMR as 1 1H NMR (500 MHz, DMSO) δ 9.22 (s, 1H, CH=N), 8.58 (d, J = 5.7 Hz, 1H), 8.52 (s, 1H), 8.29 (s, 1H), 8.11 (d, J = 5.3 Hz, 2H), 8.07 (s, 1H), 8.03 (s, 1H), 8.00 (d, J = 7.3 Hz, 1H), 7.87 (d, J = 7.5 Hz, 1H), 7.47 (t, J = 6.8 Hz, 2H), 7.40 (t, J = 6.5 Hz, 1H), 7.30 (s, 1H), 7.18 (s, 1H), 7.06 (s, 1H), 6.89 (t, J = 7.2 Hz, 1H), 6.73 (t, J = 7.5 Hz, 1H), 6.68 (d, J = 4.4 Hz, 2H), 6.00 (d, J = 6.5 Hz, 1H), 5.69 (d, J = 7.6 Hz, 1H), 3.30 (s, 3H, NCH3), 3.18–3.15 (m, 1H, CH(CH3)2)), 2.00 (m, 1H, CH(CH3)2)), 1.13 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.02 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.82 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.27 (d, J = 6.6 Hz, 3H, CH(CH3)2).

[0086] Mass spectrometry: C 39 H 39 The theoretical value of IrN5O3S is 850.24083, and the actual measured value is 850.23761, [M + H] + .

[0087] Elemental analysis. Theoretical values: C 39 H 38IrN5O3S: C, 55.17; H, 4.51; N, 8.25. Found: C, 55.32; H, 4.48; N, 8.05.

[0088] Example 5

[0089] When the complex is 5, it is prepared by the following method:

[0090] Under nitrogen protection, 36.6 mg of cycloiridium dimer (Formula (V) ), 22.8 mg of ligand (Formula (III), R2 = isopropyl), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask and reacted at room temperature for 24 h. After the reaction, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried in vacuo to obtain 30.5 mg of yellow solid 5 with a yield of 54%.

[0091] Characterized by NMR as 1 H NMR (500 MHz, DMSO) δ 9.20 (s, 1H, CH=N), 8.48 (d, J = 5.9 Hz, 1H), 8.17 (d, J = 8.6 Hz, 1H), 8.11 (s, 1H), 8.01 (d, J = 6.9 Hz, 2H), 7.91 (d, J = 6.6 Hz, 2H), 7.84 (d, J = 8.7 Hz, 1H), 7.44 (d, J = 8.6 Hz, 1H), 7.35 (t, J = 6.5 Hz, 1H), 7.29 (d, J = 2.5 Hz, 2H), 7.19 (s, 1H), 7.08 (s, 1H), 6.52 (d, 1H), 6.35 (d, J = 8.6 Hz, 1H), 5.43 (d, J = 2.4 Hz, 1H), 5.15 (d, J = 2.4 Hz, 1H), 3.48 (s, 3H, OCH3), 3.44 (s, 3H, OCH3), 3.17 (s, 3H, NCH3), 2.06–1.95 (m, 2H, CH(CH3)2)), 1.12 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.02 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.81 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.28 (d, J = 6.6 Hz, 3H, CH(CH3)2).

[0092] Mass spectrometry: C 41 H 43 Theoretical value of IrN5O5S is 910.26205, found is 910.26022, [M+H] + .

[0093] Elemental analysis. Theoretical values: C 41 H 42 IrN5O5S: C, 54.17; H, 4.66; N, 7.70. Measured values: C, 54.30; H, 4.48; N, 7.55.

[0094] Example 6

[0095] When the complex is 6, it is prepared by the following method:

[0096] Under nitrogen protection, 33.8 mg of cycloiridium dimer (Formula (V) ), 22.3 mg of ligand (Formula (III), R2 = isopropyl), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask and reacted at room temperature for 24 h. After the reaction, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared, and the precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain 37.8 mg of red solid 6 with a yield of 71%.

[0097] Characterized by NMR as 1 1H NMR (500 MHz, DMSO) δ 9.20 (s, 1H, CH=N), 8.54 (d, J = 5.7 Hz, 1H), 8.52 (s, 1H), 8.23 (d, J = 8.3 Hz, 1H), 8.08 (d, 2H), 8.03 (d, J = 7.7 Hz, 1H), 7.97 (d, J = 5.3 Hz, 2H), 7.76 (d, J = 8.0 Hz, 1H), 7.41 (t, J = 6.4 Hz, 1H), 7.38–7.34 (m, 2H), 7.28 (d, J = 2.6 Hz, 1H), 7.18 (s, 1H), 7.07 (s, 1H), 6.72 (d, J = 7.9 Hz, 1H), 6.53 (d, J = 7.6 Hz, 1H), 5.79 (s, 1H), 5.47 (s, 1H), 3.29 (s, 3H, NCH3), 3.21–3.18 (m, 1H, CH(CH3)2)), 2.03–1.98 (m, 1H, CH(CH3)2)), 1.94 (s, 3H, CH3), 1.93 (s, 3H, CH3), 1.13 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.02 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.80 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.27 (d, J = 6.6 Hz, 3H, CH(CH3)2).

[0098] Mass spectrometry: C 41 H 43 The theoretical value of IrN5O3S is 878.27211, and the actually measured value is 878.70463, [M+H] + .

[0099] Elemental analysis. Theoretical values: C 41 H 42 IrN5O3S: C, 56.15; H, 4.83; N, 7.98. The actually measured values: C, 56.30; H, 4.75; N, 7.85.

[0100] Example 7

[0101] When the complex is 7, it is prepared by the following method:

[0102] Under nitrogen protection, 53.7 mg of cycloiridium dimer (Formula (V) ) and 27.0 mg of ligand (Formula (IV), R2 = isopropyl) and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and the reaction was carried out at room temperature for 24 h. Then 19.4 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered filter and washed with n-hexane, and then dried in vacuo to obtain 61.8 mg of brown solid 7 with a yield of 65%.

[0103] NMR characterization is 11H NMR (500 MHz, DMSO) δ 9.30 (s, 1H, CH=N), 8.25–8.20 (m, 3H), 8.03–7.97 (m, 2H), 7.92 (t, J = 7.4 Hz, 1H), 7.79 (d, J = 7.7 Hz, 1H), 7.76 (s, 1H), 7.47 (d, J = 8.0 Hz, 2H), 7.43–7.37 (m, 2H), 7.33 (t, J = 6.5 Hz, 1H), 7.11 (d, J = 7.9 Hz, 2H), 7.01 (m, 2H), 6.88–6.82 (m, 2H), 6.71–6.67 (m, 2H), 6.67–6.63 (m, 2H), 6.13–6.09 (m, 1H), 5.64 (d, J = 7.7 Hz, 1H), 4.16 (s, 3H, NCH3), 3.26 (m, J = 6.3 Hz, 1H, CH(CH3)2)), 2.28 (s, 3H, CH3), 2.10–2.01 (m, 1H, CH(CH3)2)), 1.18 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.05 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.84 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.23 (d, J = 6.5 Hz, 3H, CH(CH3)2).

[0104] Mass spectrometry: C 39 H 39 The theoretical value of IrN5 is 770.28352, and the actually measured value is 770.28550, [M-(C6H4)CH3SO3] + . Elemental analysis. Theoretical values: C 46 H 46 IrN5O3S: C, 58.70; H, 4.93; N, 7.44. The actually measured values: C, 59.02; H, 4.74; N, 7.37.

[0105] Example 8

[0106] When the complex is 8, it is prepared by the following method:

[0107] Under nitrogen protection, add 48.6 mg of cycloiridium dimer (Formula (V) ) and 22.0 mg of ligand (Formula (IV), R2 = isopropyl), and 20 mL of anhydrous methanol. After reacting at room temperature for 24 h, 15.8 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction ended, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried under vacuum to obtain 56.4 mg of brown solid 8 with a yield of 69%.

[0108] Characterized by nuclear magnetic resonance as 1 1H NMR (500 MHz, DMSO) δ 9.29 (s, 1H, CH=N), 8.15–8.11 (m, 2H), 8.08 (s, 1H), 7.94 (t, J = 7.9 Hz, 1H), 7.85 (d, J = 4.1 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 7.47 (d, J = 7.9 Hz, 2H), 7.38 (d, J = 8.5 Hz, 1H), 7.28 (t, J = 6.4 Hz, 1H), 7.23 (d, J = 4.9 Hz, 1H), 7.11 (d, J = 7.8 Hz, 2H), 7.05 (s, 1H), 6.99 (d, J = 7.6 Hz, 1H), 6.87 (d, J = 7.5 Hz, 1H), 6.74 (s, 1H), 6.49 (d, 1H), 6.30 (d, J = 8.5 Hz, 1H), 5.55 (d, J = 2.3 Hz, 1H), 5.11 (d, J = 2.3 Hz, 1H), 4.15 (s, 3H, NCH3), 3.46 (s, 3H, OCH3), 3.43 (s, 3H, OCH3), 2.29 (s, 3H, CH3), 2.10–1.96 (m, 2H, CH(CH3)2)), 1.17 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 1.06 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.83 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.24 (d, J = 6.5 Hz, 3H, CH(CH3)2).

[0109] Mass spectrometry: C 41 H 43 The theoretical value of IrN5O2 is 830.30463, and the actually measured value is 830.30770, [M-(C6H4)CH3SO3] + .Elemental analysis. Theoretical values: C 48 H 50 IrN5O5S: C, 57.58; H, 5.03; N, 6.99. The actually measured values: C, 57.84; H, 4.79; N, 6.67.

[0110] Example 9

[0111] When the complex is 9, it is prepared by the following method:

[0112] Under nitrogen protection, 43.8 mg of cycloiridium dimer (Formula (Ⅴ) ), 22.0 mg of ligand (Formula (Ⅳ), R2 = isopropyl), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. After reacting at room temperature for 24 h, 15.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain 41.2 mg of red solid 9 with a yield of 55%.

[0113] The NMR characterization is 1 1H NMR (500 MHz, DMSO) δ 9.29 (s, 1H, CH=N), 8.20 (s, 1H), 8.16 (d, J = 7.6 Hz, 2H), 7.99 (d, J = 8.2 Hz, 1H), 7.92–7.87 (m, 2H), 7.74 (s, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 7.9 Hz, 2H), 7.34 (t, J = 6.5 Hz, 1H), 7.30 (t, J = 6.6 Hz, 2H), 7.11 (d, J = 7.8 Hz, 2H), 7.01 (m, 2H), 6.85 (d, J = 7.5 Hz, 1H), 6.69 (d, 2H), 6.48 (d, J = 8.6 Hz, 1H), 5.90 (s, 1H), 5.42 (s, 1H), 4.15 (s, 3H, NCH3), 2.28 (s, 3H, CH3), 2.09–2.00 (m, 2H, CH(CH3)2)), 1.93 (d, J = 6.6 Hz, 6H, CH3), 1.18 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 1.07 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 0.81 (d, J = 6.4 Hz, 3H, CH(CH3)2)), 0.23 (d, J = 6.5 Hz, 3H, CH(CH3)2).

[0114] Mass spectrometry: C 41 H 43 IrN5 theoretical value 798.31488, actually measured 798.31979, [M-(C6H4)CH3SO3] + . Elemental analysis. Theoretical value: C 48 H 50IrN5O5S: C, 59.48; H, 5.20; N, 7.23. Found: C, 59.68; H, 4.89; N, 7.07.

[0115] Example 10

[0116] When the complex is 10, it is prepared by the following method:

[0117] Under nitrogen protection, 43.8 mg of cycloiridium dimer (Formula (Ⅴ) ), 22.0 mg of ligand (Formula (Ⅳ), R2 = isopropyl), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. After reacting at room temperature for 24 h, 15.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excessive amount of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain 49.5 mg of brown solid 10 with a yield of 64%.

[0118] Characterized by NMR as 1 H NMR (500 MHz, DMSO) δ 9.29 (s, 1H, CH=N), 8.56 (d, J = 5.6 Hz, 1H), 8.30 (d, J = 8.1 Hz, 1H), 8.14 (d, J = 2.6 Hz, 1H), 8.08 (m, 2H), 7.98 (m, 2H), 7.87 (d, J = 7.6 Hz, 1H), 7.48 (t, J = 9.5 Hz, 3H), 7.41–7.36 (m, 2H), 7.31 (d, J = 2.6 Hz, 1H), 7.12 (d, J = 7.9 Hz, 2H), 7.03–6.95 (m, 2H), 6.88 (t, J = 7.5 Hz, 1H), 6.80–6.71 (m, 2H), 6.67–6.61 (m, 2H), 5.99 (d, J = 5.6 Hz, 1H), 5.67 (d, J = 7.6 Hz, 1H), 3.31 (s, 3H, NCH3), 3.16–3.07 (m, 1H, CH(CH3)2)), 2.29 (s, 3H, CH3), 1.97 (m 1H, CH(CH3)2)), 1.12 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.00 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.85 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.27 (d, J = 6.6 Hz, 3H, CH(CH3)2).

[0119] Mass spectrometry: C 39 H 39The theoretical value of IrN5 is 770.28352, and the actually measured value is 770.28550, [M-(C6H4)CH3SO3] + . Elemental analysis. Theoretical values: C 46 H 46 IrN5O3S: C, 58.70; H, 4.93; N, 7.44. The actually measured values: C, 59.02; H, 4.74; N, 7.37.

[0120] Example 11

[0121] When the complex is 11, it is prepared by the following method:

[0122] Under nitrogen protection, add 35.8 mg of cycloiridium dimer (Formula (Ⅴ) ), 20.0 mg of ligand (Formula (Ⅳ), R2 = isopropyl), and 20 mL of anhydrous methanol to a 100 mL Schlenk flask. After reacting at room temperature for 24 h, add 11.7 mg of sodium p-toluenesulfonate and stir for 12 h. After the reaction is completed, the solution is dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane is added. A precipitate appears. The precipitate is filtered through a sintered glass filter and washed with n-hexane, and then dried in vacuo to obtain 30.9 mg of brown solid 11, with a yield of 58%.

[0123] The NMR characterization is 11H NMR (500 MHz, DMSO) δ 9.24 (s, 1H, CH=N), 8.45 (d, J = 5.6 Hz, 1H), 8.16 (d, J = 8.4 Hz, 1H), 8.12 (s, 1H), 7.99 (d, J = 6.7 Hz, 2H), 7.88 (t, J = 8.8 Hz, 2H), 7.83 (d, J = 8.6 Hz, 1H), 7.47 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.2 Hz, 2H), 7.27 (d, J = 6.2 Hz, 2H), 7.11 (d, J = 8.1 Hz, 2H), 7.02 (d, J = 7.6 Hz, 1H), 6.97 (d, J = 7.6 Hz, 1H), 6.81 (d, J = 7.5 Hz, 1H), 6.51 (d, J = 8.6 Hz, 1H), 6.30 (d, J = 8.6 Hz, 1H), 5.42 (d, J = 2.3 Hz, 1H), 5.13 (d, J = 2.3 Hz, 1H), 3.45 (s, 3H, OCH3), 3.43 (s, 3H, OCH3), 3.35 (s, 3H, NCH3), 3.12 (m, 1H, CH(CH3)2)), 2.28 (s, 3H, CH3), 1.98 (m, 1H, CH(CH3)2)), 1.10 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.00 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.82 (d, J = 6.5 Hz, 3H, CH(CH3)2)), 0.27 (d, J = 6.6 Hz, 3H, CH(CH3)2).

[0124] Mass spectrometry: C 41 H 43 The theoretical value of IrN5O2 is 830.30463, and the actual measured value is 830.30770, [M-(C6H4)CH3SO3] + . Elemental analysis. Theoretical values: C 48 H 50 IrN5O5S: C, 57.58; H, 5.03; N, 6.99. The actual measured values: C, 57.84; H, 4.79; N, 6.67.

[0125] Example 12

[0126] When the complex is 12, it is prepared by the following method:

[0127] Under nitrogen protection, 31.6 mg of cycloiridium dimer (Formula (V) ) and 21.0 mg of ligand (Formula (IV), R2 = isopropyl), and 20 mL of anhydrous methanol. After reacting at room temperature for 24 h, 10.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in a small amount of dichloromethane, and then an excess of poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered filter and washed with n-hexane, and then dried under vacuum to obtain 32.8 mg of yellow solid 12, with a yield of 60%.

[0128] Characterized by nuclear magnetic resonance as 1 1H NMR (500 MHz, DMSO) δ 9.25 (s, 1H, CH=N), 8.52 (d, J = 5.8 Hz, 1H), 8.23 (d, J = 8.1 Hz, 1H), 8.07 (m, 3H), 7.95 (d, J = 4.0 Hz, 2H), 7.76 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.0 Hz, 2H), 7.38 (m, 2H), 7.27 (d, J = 8.1 Hz, 2H), 7.12 (d, J = 7.9 Hz, 2H), 7.00 (m, 2H), 6.81 (d, J = 7.4 Hz, 1H), 6.72 (d, J = 7.7 Hz, 1H), 6.49 (d, J = 7.8 Hz, 1H), 5.77 (s, 1H), 5.46 (s, 1H), 3.29 (s, 3H, NCH3), 3.17–3.14 (m, 1H, CH(CH3)2)), 2.29 (s, 3H), 2.00–1.96 (m, 1H, CH(CH3)2)), 1.93 (d, J = 3.5 Hz, 6H, CH3), 1.12 (d, J = 6.6 Hz, 3H, CH(CH3)2)), 1.01 (d, J = 6.7 Hz, 3H, CH(CH3)2)), 0.82 (d, J = 6.4 Hz, 3H, CH(CH3)2)), 0.28 (d, J = 6.6 Hz, 3H, CH(CH3)2)).

[0129] Mass spectrometry: C 41 H 43 The theoretical value of IrN5 is 798.31488, and the actually measured value is 798.31979, [M-(C6H4)CH3SO3] + . Elemental analysis. Theoretical values: C 48 H 50 IrN5O5S: C, 59.48; H, 5.20; N, 7.23. The actually measured values: C, 59.68; H, 4.89; N, 7.07.

[0130] Example 13

[0131] Proliferation inhibition activity experiment of the complex 1-12 tumor cell lines with anti-cancer activity:

[0132] (1) Preparation of the compound to be tested: Dissolve the solid complex in DMSO to prepare a stock solution with a certain concentration, and further dilute the stock solution with cell culture medium until the working concentration is reached, and culture for 24 h;

[0133] (2) Cell growth inhibition experiment (MTT method):

[0134] 1) Take 5000 human cervical cancer cells (HeLa), human non-small cell lung cancer cells (A549), and human hepatoma cells (HepG2) respectively, prepare cell suspensions, and inoculate them in 96-well culture plates;

[0135] 2) Pre-culture the cells with drug-free medium, incubate at 5% CO2 and 310 K for 24 h, add the prepared compound to be tested, and culture for 24 h;

[0136] 3) Add 15 μL of 5 mg / mL MTT solution to each well and continue to culture for 4 h to form purple crystalline formazan;

[0137] 4) Terminate the culture, carefully aspirate the culture medium in the wells, add 100 μL of DMSO to each well to fully dissolve the formazan precipitate, mix well with an oscillator, and measure the optical density value of each well with an enzyme-linked immunosorbent assay (ELISA) reader at a wavelength of 570 nm;

[0138] 5) Repeat each experiment three times, IC 50 = mean ± SEM. The inhibition rates of complexes 1-12 and commercially available cisplatin on the growth of cancer cells HeLa, A549, and HepG2 are shown in Table 1.

[0139] Table 1

[0140]

[0141] It can be seen from Example 13 that the activity of the cationic complex is close to or exceeds that of cisplatin, the zwitterionic complex has certain activity but is lower than that of cisplatin. And by comparison, it can be seen that the anticancer activity of the cationic complex is significantly better than that of the zwitterionic complex. The above conclusions provide a theoretical basis for the preparation of new antitumor drugs.

[0142] Obviously, those skilled in the art can make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. Thus, if these modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalent technologies, the present invention is also intended to include these modifications and variations.

Claims

1. A cyclometalated iridium(III) complex, characterized in that, The structural formulas are as shown in Formulas (Ⅰ) and (Ⅱ): ； （Ⅰ） （Ⅱ） In the formula (I), R1 is , R2 is isopropyl, is , and the specific structural formula is as shown in Formula 1; in the formula (I), R1 is , R2 is isopropyl, is , and the specific structural formula is as shown in Formula 2; in the formula (I), R1 is , R2 is isopropyl, is , and the specific structural formula is as shown in Formula 3; in the formula (I), R1 is , R2 is isopropyl, is , and the specific structural formula is as shown in Formula 4; in the formula (I), R1 is , R2 is isopropyl, is , and the specific structural formula is as shown in Formula 5; in the formula (I), R1 is , R2 is isopropyl, is , and the specific structural formula is as shown in Formula 6; in the formula (II), R1 is , R2 is isopropyl, is , X is , and the specific structural formula is as shown in Formula 7; in the formula (II), R1 is , R2 is isopropyl, is , X is , and the specific structural formula is as shown in Formula 8; in the formula (II), R1 is , R2 is isopropyl, is , X is , and the specific structural formula is as shown in Formula 9; in the formula (II), R1 is , R2 is isopropyl, is , X is , and the specific structural formula is as shown in Formula 10; in the formula (II), R1 is , R2 is isopropyl, is , X is , and the specific structural formula is as shown in Formula 11; in the formula (II), R1 is , R2 is isopropyl, is , X is , and the specific structural formula is as shown in Formula 12: 。 2. A method for preparing the cyclometalated iridium(III) complex according to claim 1, characterized in that, It includes the following steps: Under nitrogen protection, the dimer shown in Formula (Ⅴ) and the ligand shown in Formula (Ⅲ) are reacted in methanol as the solvent, and the reaction system reacts at room temperature for 24 h to obtain Formula (Ⅰ); under nitrogen protection, the dimer shown in Formula (Ⅴ) and the ligand shown in Formula (Ⅳ) are reacted in methanol as the solvent, and after the reaction system reacts at room temperature for 24 h, AX is added and the reaction continues for 12 h to obtain Formula (Ⅱ); the inorganic salt AX is one of NaX, KX, and NH4X; the specific synthesis route is: 。 3. According to the preparation method described in claim 2, characterized in that When the complex is 1, it is prepared by the following method: Under nitrogen protection, 46.2 mg of the cycloiridium dimer of formula (V), 32.0 mg of the ligand of formula (III), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (III), R1 = , R2 = isopropyl. The reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried in vacuo to obtain a brown solid 1; When the complex is 2, it is prepared by the following method: Under nitrogen protection, 36.6 mg of the cycloiridium dimer of formula (V), 22.8 mg of the ligand of formula (III), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , in formula (III), R1 = , R2 = isopropyl. The reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a red solid 2; When the complex is 3, it is prepared by the following method: Under nitrogen protection, 33.8 mg of the cycloiridium dimer of formula (V), 22.3 mg of the ligand of formula (III), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (III), R1 = , R2 = isopropyl. The reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was evaporated to dryness with a rotary evaporator, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried under vacuum to obtain a red solid 3; When the complex is 4, it is prepared by the following method: Under nitrogen protection, 45.4 mg of the cycloiridium dimer of formula (V), 31.5 mg of the ligand of formula (III), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (III), R1 = , R2 = isopropyl. The reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a yellow solid 4; When the complex is 5, it is prepared by the following method: Under nitrogen protection, 36.6 mg of the cycloiridium dimer of formula (V), 22.8 mg of the ligand of formula (III), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (III), R1 = , R2 = isopropyl. The reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain a yellow solid 5; When the complex is 6, it is prepared by the following method: Under nitrogen protection, 33.8 mg of the cycloiridium dimer of formula (V), 22.3 mg of the ligand of formula (III), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , in formula (III), R1 = , R2 = isopropyl. The reaction was carried out at room temperature for 24 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain a red solid 6; When the complex is 7, it is prepared by the following method: Under nitrogen protection, 53.7 mg of the cycloiridium dimer of formula (V), 27.0 mg of the ligand of formula (IV), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (IV), R1 = , R2 = isopropyl. After reacting at room temperature for 24 h, 19.4 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain 7 as a brown solid; When the complex is 8, it is prepared by the following method: Under nitrogen protection, 48.6 mg of the cycloiridium dimer of formula (V), 22.0 mg of the ligand of formula (IV), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , in formula (IV), R1 = , R2 = isopropyl. After reacting at room temperature for 24 h, 15.8 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain 8 brown solids; When the complex is 9, it is prepared by the following method: Under nitrogen protection, 43.8 mg of the cycloiridium dimer of formula (V), 22.0 mg of the ligand of formula (IV), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , in formula (IV), R1 = , R2 = isopropyl. After reacting at room temperature for 24 h, 15.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered funnel and washed with n-hexane, and then dried in vacuo to obtain 9 as a red solid; When the complex is 10, it is prepared by the following method: Under nitrogen protection, 43.8 mg of the cycloiridium dimer of formula (V), 22.0 mg of the ligand of formula (IV), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (IV), R1 = , R2 = isopropyl. After reacting at room temperature for 24 h, 15.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried in vacuo to obtain 10 mg of a brown solid; When the complex is 11, it is prepared by the following method: Under nitrogen protection, 35.8 mg of the cycloiridium dimer of formula (V), 20.0 mg of the ligand of formula (IV), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , and in formula (IV), R1 = , R2 = isopropyl. After reacting at room temperature for 24 h, 11.7 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass funnel and washed with n-hexane, and then dried in vacuo to obtain 11 mg of a brown solid; When the complex is 12, it is prepared by the following method: Under nitrogen protection, 31.6 mg of the cycloiridium dimer of formula (V), 21.0 mg of the ligand of formula (IV), and 20 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (V), = , in formula (IV), R1 = , R2 = isopropyl. After reacting at room temperature for 24 h, 10.9 mg of sodium p-toluenesulfonate was added and stirred for 12 h. After the reaction was completed, the solution was dried by rotary evaporation, dissolved in dichloromethane, and then an excess of the poor solvent n-hexane was added. A precipitate appeared. The precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried in vacuo to obtain 12 mg of a yellow solid.

4. An application of the cyclometalated iridium(Ⅲ) complex described in claim 1 in the preparation of anticancer drugs, wherein the cancer is liver cancer, lung cancer, or cervical cancer.

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