An [N,NH2] cyclometalated iridium(III) cationic complex with anticancer activity, its preparation method and application

Abstract

The present invention discloses an [N,NH2] cyclometalated iridium(III) cationic complex with anticancer activity, and its preparation method and application. The structural formula of the complex is shown in Formula (I), and is one of #imgabs0#, and the structural formula is #imgabs1##imgabs2#. Wherein the ligand reacts with the cycloiridium under reaction conditions, and after adding an inorganic salt AX to the reaction system, the [N,NH2] cyclometalated iridium(III) cationic complex I is obtained; wherein [N,NH2] is a neutral ligand, and the purpose of adding AX is to use it as a counter anion to make the cationic complex precipitate and separate more easily. These complexes exhibit good anticancer activity, and their performance is close to or even better than that of commercially available cisplatin, and they are very promising anticancer drugs. #imgabs3#

Description

Technical Field:

[0001] The present invention relates to metal complexes, and specifically to an [N,NH2] cyclometalated iridium(III) cationic complex with anti-cancer activity, its preparation method and application, belonging to the field of chemical pharmacy. Background Art:

[0002] With the development of technology, cancer is gradually being cured by various means (such as surgical resection, radiotherapy, chemotherapy, etc.) from an "incurable disease". The most classic drug in chemotherapy is cisplatin. Since cisplatin was discovered and applied in the anti-cancer field, various drugs (such as carboplatin and oxaliplatin, etc.) have been continuously developed. Metal complexes have been widely studied due to their structural diversity, the possibility of ligand exchange, and covalent interactions with biomolecular targets. Among many metal complex drugs, cyclometalated iridium complexes have their own unique advantages (stable chemical properties, broader anti-tumor spectrum, unique mechanism of action, low toxicity and side effects, etc.), and have received people's attention. The structure of cyclometalated iridium complexes is a six-coordination mode of three bidentate chelating ligands. Among them, the most studied are neutral iridium complexes and cationic iridium complexes. For example, in the neutral cycloiridium complex (a), the [X,Y] chelating ligand is an anionic (negative monovalent) ligand, and the complex is neutral without the presence of counterions. In the cationic cycloiridium complex (b), the [X,Y] chelating ligand is a neutral ligand, the inner sphere of the complex is a cationic metal center, and there is an anion PF6 - as a counterion. Based on the unique coordination mode and chelating structure of the cationic complex of cyclometalated iridium(III) [N,NH2] neutral chelating ligand and the unique advantages of iridium metal, it is expected to develop metal anti-cancer drugs with higher anti-cancer activity, lower toxicity and side effects, and a novel anti-cancer mechanism.

[0003] Summary of the Invention:

[0004] A series of [N,NH2] ligands containing different substituents and cycloiridium containing different are introduced in the hope of obtaining a series of [N,NH2] cyclometalated iridium(III) cationic complexes with good anti-tumor effects. Such [N,NH2] cyclometalated iridium(III) cationic complexes exhibit excellent anti-tumor effects.

[0005]

[0006] The molecular structural formula of the [N,NH2] cyclometalated iridium(III) cationic complex is:

[0007]

[0008] In the formula, R1 and R2 are simultaneously or respectively hydrogen, C1-C 15 alkyl, halogen or halogenated C1-C 15 alkyl; is one of; X is Cl - , PF6 - , BF4 - , BPh4 - , SbF6 - , one of.

[0009] For the [N, NH2] cyclometalated iridium(III) cationic complex of the present invention, in formula (I), R1 is tert-butyl, R2 is hydrogen, and X is PF6 - , is The specific structural formula is as shown in formula 1; in formula (I), R1 is tert-butyl, R2 is hydrogen, and X is PF6 - , is The specific structural formula is as shown in formula 2; in formula (I), R1 is methyl, R2 is hydrogen, and X is PF6 - , is The specific structural formula is as shown in formula 3; in formula (I), R1 is methoxy, R2 is hydrogen, and X is PF6 - , is The specific structural formula is as shown in formula 4; in formula (I), R1 is methoxy, R2 is hydrogen, and X is PF6 - , is The specific structural formula is as shown in formula 5;

[0010]

[0011] The preparation method of the [N, NH2] cyclometalated iridium(III) cationic complex of the present invention includes the following steps: Under an argon atmosphere, the dimer shown in formula (III), the ligand shown in formula (II), and the inorganic salt AX are reacted in methanol as the solvent. After the reaction system is stirred at room temperature for 6 h, the cyclometalated iridium(III) [N, NH2] chelating ligand cationic complex shown in formula (I) is obtained; the inorganic salt AX is one of N inorganic salt AX, KX, AgX or NH4X; the specific synthesis route is:

[0012]

[0013] When the complex is 1, it is prepared by the following method:

[0014] Under an argon atmosphere, 53.86 mg of the cycloiridium dimer (Formula (Ⅲ) ) was added to a 100 mL Schlenk flask, along with 25.36 mg of the ligand (Formula (Ⅱ), R2 = hydrogen, R1 = tert-butyl), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 1.

[0015] When the complex is 2, it is prepared by the following method:

[0016] Under an argon atmosphere, 56.57 mg of the cycloiridium dimer (Formula (Ⅲ) ) was added to a 100 mL Schlenk flask, along with 22.35 mg of the ligand (Formula (Ⅱ), R2 = hydrogen, R1 = tert-butyl), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 2.

[0017] When the complex is 3, it is prepared by the following method:

[0018] Under an argon atmosphere, 56.97 mg of the cycloiridium dimer (Formula (Ⅲ) ) was added to a 100 mL Schlenk flask, along with 24.12 mg of the ligand (Formula (Ⅱ), R2 = hydrogen, R1 = methyl), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain reddish-brown solid 3.

[0019] When the complex is 4, it is prepared by the following method:

[0020] Under an argon atmosphere, 64.65 mg of the cycloiridium dimer (Formula (Ⅲ) )、27.27 mg of ligand (in formula (II), R2 = hydrogen, R1 = methoxy), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added, and the mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, and the precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 4.

[0021] When the complex is 5, it is prepared by the following method:

[0022] Under an argon atmosphere, 60.16 mg of cycloiridium dimer (in formula (III) )、22.82 mg of ligand (in formula (II), R2 = hydrogen, R1 = methoxy), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and the mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, and the precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 5.

[0023] Beneficial effects:

[0024] (1) The present invention provides a preparation method of [N,NH2] cyclometalated iridium(III) cationic complexes, aiming to obtain a series of [N,NH2] cyclometalated iridium(III) cationic complexes with good anti-tumor effects.

[0025] (2) The synthesis of the complex is carried out by reacting a ligand, a dimer, and an inorganic salt AX under reaction conditions to obtain [N,NH2] cyclometalated iridium(III) cationic complex I.

[0026] (3) Such [N,NH2] cyclometalated iridium(III) cationic complexes 1-5 exhibit excellent anti-tumor effects, and some of their properties are even better than those of commercial cisplatin, making them very promising anti-cancer drugs.

[0027] Contents of the drawings:

[0028] Figure 1 1H NMR spectrum of complex 1 of the present invention.

[0029] Figure 2 Mass spectrum of complex 1 of the present invention.

[0030] Figure 3 1H NMR spectrum of complex 2 of the present invention.

[0031] Figure 4 Mass spectrum of complex 2 of the present invention.

[0032] Figure 5 1H NMR spectrum of Complex 3 of the present invention

[0033] Figure 6 Mass spectrum of Complex 3 of the present invention.

[0034] Figure 7 1H NMR spectrum of Complex 4 of the present invention

[0035] Figure 8 Mass spectrum of Complex 4 of the present invention.

[0036] Figure 9 1H NMR spectrum of Complex 5 of the present invention

[0037] Figure 10 Mass spectrum of Complex 5 of the present invention. Detailed implementation method:

[0038] The present invention is further illustrated by the following examples of some representative compounds, but these descriptions do not limit the present invention.

[0039] The starting compounds used in the synthesis of the compounds are commercial products or can be prepared from known synthetic methods. The preparation methods of all organic compounds can be obtained from the literature, and these methods are basic and obvious to synthetic chemists. Therefore, the following descriptions of the synthesis methods can be considered detailed and specific.

[0040] Example 1

[0041] When the complex is 1, it is prepared by the following method:

[0042] Under an argon atmosphere, 53.86 mg of cycloiridium dimer (Formula (Ⅲ) ), 25.36 mg of ligand (Formula (Ⅱ), R2 = hydrogen, R1 = tert-butyl), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and the mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, and the precipitate was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 1.

[0043] Characterized by NMR as 11H NMR (500 MHz, CDCl3) δ 8.66 (d, J = 4.6 Hz, 1H), 8.11 (s, 1H, CH=N), 7.92 (d, J = 1.9 Hz, 1H), 7.85–7.76 (m, 1H), 7.70 (d, J = 8.3 Hz, 1H), 7.60 (t, J = 7.8 Hz, 1H), 7.52 (d, J = 8.0 Hz, 1H), 7.32 (d, J = 7.5 Hz, 1H), 7.29 (d, J = 8.1 Hz, 1H), 7.10–7.05 (m, 2H), 7.01 (d, J = 7.8 Hz, 1H), 6.86 (t, J = 7.5 Hz, 1H), 6.74–6.67 (m, 2H), 6.67–6.62 (m, 3H), 6.56 (t, J = 7.4 Hz, 1H), 6.46 (d, J = 10.9 Hz, 1H), 6.34 (d, J = 7.0 Hz, 1H), 6.12 (d, J = 7.5 Hz, 1H), 6.01 (d, J = 7.6 Hz, 1H), 5.96 (d, J = 8.2 Hz, 2H), 1.11 (s, 9H, C(CH3)3).

[0044] Mass spectrometry: C 39 H 36 Theoretical value of IrPF6N4 is 753.25692, and the actually measured value is 753.25582, [M - PF6] + .

[0045] Elemental analysis. Theoretical values: C 39 H 36 For IrPF6N4: C, 52.17; H, 4.04; N, 6.24. Actually measured: C, 52.59; H, 3.77; N, 6.04.

[0046] Example 2

[0047] When the complex is 2, it is prepared by the following method:

[0048] Under an argon atmosphere, 56.57 mg of cycloiridium dimer (Formula (Ⅲ) ), 22.35 mg of ligand (Formula (Ⅱ), R2 = hydrogen, R1 = tert - butyl), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and the mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n - hexane. A precipitate appeared, which was filtered through a sintered glass filter, washed with n - hexane, and dried under vacuum to obtain a yellow solid 2.

[0049] The NMR characterization is as follows 11H NMR (500 MHz, CDCl3) δ 8.67 (s, 1H), 8.23 (s, 1H, CH=N), 7.93 (d, J = 5.6 Hz, 1H), 7.61 (d, J = 3.9 Hz, 1H), 7.53 (d, J = 8.7 Hz, 1H), 7.45–7.40 (m, 2H), 7.23 (s, 1H), 7.16 (d, J = 8.4 Hz, 2H), 7.04 (d, J = 8.7 Hz, 2H), 6.73 (d, J = 8.4 Hz, 2H), 6.63 (t, J = 5.3 Hz, 2H), 6.52 (m, 1H), 6.45 (s, 1H), 6.36 (m, 1H), 6.11 (d, J = 8.3 Hz, 2H), 5.71 (d, J = 2.4 Hz, 1H), 5.61 (d, J = 2.4 Hz, 1H), 3.54 (s, 3H, OCH3), 3.51 (s, 3H, OCH3), 1.18 (s, 9H, C(CH3)3).

[0050] Mass spectrometry: C 41 H 40 The theoretical value of IrO2PF6N4 is 813.27805, and the actually measured value is 813.27531, [M - PF6] + .

[0051] Elemental analysis. Theoretical values: C 41 H 40 For IrO2PF6N4: C, 51.41; H, 4.21; N, 5.85. The actually measured values are: C, 51.79; H, 3.98; N, 5.63.

[0052] Example 3

[0053] When the complex is 3, it is prepared by the following method:

[0054] Under an argon atmosphere, 56.97 mg of the cycloiridium dimer (Formula (Ⅲ) ), 24.12 mg of the ligand (Formula (Ⅱ), R2 = hydrogen, R1 = methyl), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and stirred at room temperature for 6 h. After the reaction, the solution was dried by rotary evaporation, the residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter; the filtrate was recrystallized by the diffusion method of dichloromethane and n - hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n - hexane, and then dried in vacuo to obtain a reddish - brown solid 3.

[0055] The NMR characterization is as follows 11H NMR (500 MHz, CDCl3) δ 8.77 (s, 1H), 8.17 (s, 1H, CH=N), 8.02 (d, J = 5.7 Hz, 1H), 7.93 (dd, J = 13.9, 5.7 Hz, 1H), 7.77 (d, J = 8.1 Hz, 1H), 7.69 (d, J = 7.5 Hz, 1H), 7.65–7.59 (m, 2H), 7.48–7.41 (m, 2H), 7.31 (s, 1H), 7.15 (t, J = 3.5 Hz, 2H), 6.98–6.92 (m, 2H), 6.79 (m, 3H), 6.72 (d, J = 7.0 Hz, 1H), 6.65 (d, J = 7.3 Hz, 1H), 6.52 (d, J = 7.9 Hz, 2H), 6.19 (d, J = 7.6 Hz, 1H), 6.09 (d, J = 7.8 Hz, 1H), 6.04 (s, 1H), 2.15 (s, 3H, CH3).

[0056] Mass spectrometry: C 36 H 30 Theoretical value of IrPF6N4 is 711.20997, and the actual measured value is 711.20713, [M - PF6] + .

[0057] Elemental analysis. Theoretical value: C 36 H 30 For IrPF6N4: C, 50.52; H, 3.53; N, 6.55. The actual measured values are: C, 50.78; H, 3.24; N, 6.19.

[0058] Example 4

[0059] When the complex is 4, it is prepared by the following method:

[0060] Under an argon atmosphere, 64.65 mg of the cycloiridium dimer (Formula (Ⅲ) ), 27.27 mg of the ligand (Formula (Ⅱ), R2 = hydrogen, R1 = methoxy), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and the mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n - hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n - hexane, and then dried in vacuo to obtain the yellow solid 4.

[0061] The NMR characterization is as follows 11H NMR (500 MHz, CDCl3) δ 8.76 (d, J = 4.0 Hz, 1H), 8.20 (s, 1H, CH=N), 8.01 (d, J = 5.6 Hz, 1H), 7.97–7.83 (m, 1H), 7.77 (d, J = 8.2 Hz, 1H), 7.69 (t, J = 7.8 Hz, 1H), 7.65–7.56 (m, 2H), 7.47 (d, J = 7.9 Hz, 1H), 7.42 (d, J = 8.4 Hz, 1H), 7.29 (s, 1H), 7.21 (d, J = 8.0 Hz, 1H), 7.15 (d, J = 6.1 Hz, 1H), 6.94 (t, J = 7.1 Hz, 1H), 6.79 (m, 2H), 6.72 (t, J = 6.6 Hz, 1H), 6.65 (t, J = 7.4 Hz, 1H), 6.57–6.49 (m, 1H), 6.44 (d, J = 6.9 Hz, 1H), 6.25 (d, J = 8.7 Hz, 2H), 6.19 (d, J = 7.6 Hz, 1H), 6.11 (t, J = 7.4 Hz, 2H), 3.65 (s, 3H, OCH3).

[0062] Mass spectrometry: C 36 H 30 Theoretical value of IrOPF6N4 is 727.20489, and the actually measured value is 727.20152, [M - PF6] + .

[0063] Elemental analysis. Theoretical values: C 36 H 30 IrOPF6N4: C, 49.60; H, 3.47; N, 6.43. Actually measured: C, 49.89; H, 3.16; N, 6.22.

[0064] Example 5

[0065] When the complex is 5, it is prepared by the following method:

[0066] Under an argon atmosphere, 60.16 mg of the cycloiridium dimer (Formula (Ⅲ) ), 22.82 mg of the ligand (Formula (Ⅱ), R2 = hydrogen, R1 = methoxy), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask, and the mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n - hexane. A precipitate appeared, and the precipitate was filtered through a sintered glass filter and washed with n - hexane, and then dried in vacuo to obtain a yellow solid 5.

[0067] The NMR characterization is 11H NMR (500 MHz, CDCl3) δ 8.74 (d, J = 5.1 Hz, 1H), 8.32 (s, 1H, CH=N), 7.95 (d, J = 5.5 Hz, 1H), 7.79 (m, 2H), 7.66–7.61 (m, 2H), 7.56–7.52 (m, 2H), 7.44 (d, J = 5.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.14 (d, J = 7.4 Hz, 2H), 6.62 (d, J = 6.9 Hz, 1H), 6.51 (d, J = 5.2 Hz, 2H), 6.39 (d, J = 8.6 Hz, 1H), 6.30 (d, J = 8.8 Hz, 2H), 6.23 (d, J = 8.7 Hz, 2H), 5.71 (d, J = 2.2 Hz, 1H), 5.65 (d, J = 2.3 Hz, 1H), 3.65 (s, 3H, OCH3), 3.53 (s, 3H, OCH3), 3.52 (s, 3H, OCH3).

[0068] Mass spectrometry: C 38 H 34 Theoretical value of IrO3PF6N4 is 787.22601, actually measured value is 787.22371, [M - PF6] + .

[0069] Elemental analysis. Theoretical value: C 36 H 30 IrOPF6N4: C, 48.98; H, 3.68; N, 6.01. Actually measured: C, 49.15; H, 3.49; N, 5.77.

[0070] Example 6

[0071] Proliferation inhibition activity experiment of complexes 1 - 5 with anticancer activity on tumor cell lines:

[0072] (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;

[0073] (2) Cell growth inhibition experiment (MTT method):

[0074] 1) Take 5000 human cervical cancer cells (HeLa), human non - small cell lung cancer cells (A549), human hepatocellular carcinoma cells (HepG2) and human lung adenocarcinoma cisplatin - resistant cells (A549 / DDP) respectively to prepare cell suspensions, and inoculate them into 96 - well culture plates;

[0075] 2) Pre-culture the cells in a drug-free medium, incubate at 310K with 5% CO2 for 24 hours, add the prepared test compound, and culture for 24h;

[0076] 3) Add 15 μL of 5 mg / mL MTT solution to each well and continue to culture for 4 hours to form purple crystalline formazan;

[0077] 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. After mixing with an oscillator, measure the optical density value of each well with an ELISA reader at a wavelength of 570 nm;

[0078] 5) Repeat each experiment three times, IC 50 = mean ± SEM. The inhibition rates of complexes 1-5 and commercial cisplatin on the growth of cancer cells HeLa, A549, HepG2 and A549 / DDP are shown in Table 1.

[0079] Table 1

[0080]

[0081] It can be seen from Example 6 that complexes 1-5 all exhibit very good anti-cancer activities, approaching or superior to the activity of commercial cisplatin. The above data show that with the change of substituents, the anti-cancer activity also changes accordingly. In addition, the cytotoxicity of the complexes against cisplatin-resistant cells was detected and found to have good activity, and there is None no cross-resistance with cisplatin. The above conclusions provide a theoretical basis for the preparation of new anti-tumor drugs.

[0082] Obviously, those skilled in the art can make various modifications and variations 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. [N,NH2] cyclometalated iridium(III) cationic complex, characterized in that, The structural formula is as shown in formula (I): ； （Ⅰ） In formula (I), R1 is tert-butyl, R2 is hydrogen, and X is PF6 - , is , and the specific structural formula is as shown in formula 1; in the said formula (I), R1 is tert-butyl, R2 is hydrogen, and X is PF6 - , is , and the specific structural formula is as shown in formula 2; in the said formula (I), R1 is methyl, R2 is hydrogen, and X is PF6 - , is , and the specific structural formula is as shown in formula 3; in the said formula (I), R1 is methoxy, R2 is hydrogen, and X is PF6 - , is , and the specific structural formula is as shown in formula 4; in the said formula (I), R1 is methoxy, R2 is hydrogen, and X is PF6 - , is , and the specific structural formula is as shown in formula 5; 。 2. A method for preparing the [N,NH2] cyclometalated iridium(III) cationic complex according to claim 1, characterized in that, It includes the following steps: Under an argon atmosphere, the dimer shown by formula (III), the ligand shown by formula (II) and the inorganic salt AX are reacted in methanol as a solvent. After the reaction system is stirred at room temperature for 6 h, the [N,NH2] cyclometalated iridium(III) cationic complex shown by formula (I) is obtained; the inorganic salt AX is one of NaX, KX, AgX and NH4X; the specific synthesis route is as follows: 。 Ⅱ Ⅲ Ⅰ 3. The preparation method according to claim 2, wherein When the complex is 1, it is prepared by the following method: Under an argon atmosphere, 53.86 mg of the cycloiridium dimer of formula (III), 25.36 mg of the ligand of formula (II), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (III), = , in the ligand of formula (II), R2 = hydrogen and R1 = tert-butyl. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 1; When the complex is 2, it is prepared by the following method: Under an argon atmosphere, 56.57 mg of the cycloiridium dimer of formula (III), 22.35 mg of the ligand of formula (II), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (III), = , in the ligand of formula (II), R2 = hydrogen and R1 = tert-butyl. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain yellow solid 2; When the complex is 3, it is prepared by the following method: Under an argon atmosphere, 56.97 mg of the cycloiridium dimer of formula (III), 24.12 mg of the ligand of formula (II), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (III), = , in the ligand of formula (II), R2 = hydrogen and R1 = methyl. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was dried by rotary evaporation. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain 3 as a reddish-brown solid; When the complex is 4, it is prepared by the following method: Under an argon atmosphere, 64.65 mg of the cycloiridium dimer of formula (III), 27.27 mg of the ligand of formula (II), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (III), = , in the ligand of formula (II), R2 = hydrogen and R1 = methoxy. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, which was filtered through a sintered glass filter and washed with n-hexane, and then dried under vacuum to obtain a yellow solid 4; When the complex is 5, it is prepared by the following method: Under an argon atmosphere, 60.16 mg of the cycloiridium dimer of formula (III), 22.82 mg of the ligand of formula (II), 33 mg of hexafluorophosphate, and 10 mL of anhydrous methanol were added to a 100 mL Schlenk flask. In formula (III), = , in the ligand of formula (II), R2 = hydrogen and R1 = methoxy. The mixture was stirred at room temperature for 6 h. After the reaction was completed, the solution was evaporated to dryness using a rotary evaporator. The residue was dissolved in dichloromethane, and the excess hexafluorophosphate was removed by filtration through a sintered glass filter. The filtrate was recrystallized by the diffusion method using dichloromethane and n-hexane. A precipitate appeared, and the precipitate was filtered through a sintered glass filter and washed with n-hexane, followed by drying under vacuum to obtain 5 as a yellow solid.

4. Use of the [N,NH2] cyclometalated iridium(III) cationic complex according to claim 1 in the preparation of an anticancer drug, wherein the cancer is liver cancer, lung cancer or cervical cancer.

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