2, 6-di-tert-butyl pyrene-indolizine phenothiazine compound, preparation method thereof and application of compound in aspect of anti-cancer drugs

Abstract

The invention belongs to the technical field of organic synthesis and medicinal chemistry, and particularly relates to a synthesis method of a novel polycyclic aromatic hydrocarbon derivate 2, 6-di-tert-butyl pyrene and indolizine phenothiazine compound and application of the compound in the aspect of anti-cancer drugs. The synthesis process is simple and convenient, conditions are mild, and the yield is ideal. Pharmacodynamic evaluation shows that the compound shows strong inhibitory activity on various human cancer cell lines, and the IC50 values are respectively cervical cancer Hela cells (0.17 mu M), lung cancer A549 cells (0.3 mu M), prostatic cancer PC-3 cells (0.42 mu M) and liver cancer HepG2 cells (10.79 mu M), which are respectively reduced by 109 times, 173 times, 35 times and 1.8 times compared with positive control drug cis-platinum. In addition to efficiently inhibiting cancer cells, the compound has low toxicity to normal cells, meets the basic requirements of excellent anti-cancer drugs, and shows important application value and potential in the field of research and development of novel anti-cancer drugs.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis and medicinal chemistry, specifically relating to a method for synthesizing a novel polycyclic aromatic hydrocarbon derivative, 2,6-di-tert-butylpyrene-indenephenothiazine compound, and its application in anticancer drugs. Background Technology

[0002] Cancer remains a leading threat to global public health, and its prevention and treatment remain a serious challenge. Global statistics from 2022 show approximately 20 million new cancer cases and 9.7 million cancer deaths. Common malignant tumors such as breast cancer, lung cancer, prostate cancer, and cervical cancer account for about 35% of all cancer incidence and mortality. [Bray, F., Laversanne, M., Sung, H., Ferlay, J., Siegel, RL, Soerjomataram, I., Jemal, A.CA. Cancer. J. Clin., 2024, 74, 229-263.] While currently widely used chemotherapy drugs (such as cisplatin, paclitaxel, 5-fluorouracil, and cyclophosphamide) possess broad-spectrum antitumor activity, their significant toxic side effects severely impact long-term treatment outcomes for patients. [Dasari, S., Tchounwou, PBEJ Pharmacol., 2014, 740, 364-378; Staff, NP, Fehrenbacher, Jill, C., Caillaud, M., Damaj, MI, Segal, RA, Rieger, S. Exp. Neurol., 2020, 324, 113-121; LO, EKK, Leung, HKM, Zhang, F., El-Nezami, H. Curr. Opin. Toxicol., 2023, 36, 100-423; Ibrahim, KM, Darwish, SF, Mantawy, EM, El-demerdash, E. Mol. Cell. Biochem., 2024, 479, 1873-1893.] This therapeutic bottleneck highlights the urgent need to develop novel, highly effective, and low-toxicity anticancer drugs.

[0003] Phenothiazines, a class of thiazide heterocyclic compounds with a butterfly-like structure, have a molecular skeleton composed of a nitrogen-sulfur heterocyclic core fused with two benzene rings, forming a unique bicyclic fused system. This special spatial configuration and excellent electronic properties make them valuable for applications in materials science, medicinal chemistry, and petrochemicals. [Luo, J.-S., Wan, Z.-Q., Jia, C.-Y. Chinese. Chem. Lett., 2016, 27, 1304-1318; Revoju, S., Matuhina, A., Canil, L., Salonen, H., Hiltunen, A., Abate, A., Vivo, PJ Mater. Chem. C., 2020, 8, 15486-15506.] With the deepening research on this molecular skeleton, its chemical modification and functionalization have become current research hotspots. Current research on phenothiazine drugs largely focuses on the modification of the core nitrogen-sulfur heterocycle and the structural alteration of the two benzene rings. However, research on enhancing molecular conjugation through extended π-conjugation systems to construct novel conjugated phenothiazine derivatives remains relatively limited. This synthetic strategy not only enables the construction of novel phenothiazine derivatives but also provides an important material basis for expanding their multifunctional applications. Summary of the Invention

[0004] Based on the above, this invention provides a method for synthesizing a novel polycyclic aromatic hydrocarbon derivative—2,6-di-tert-butylpyrene-indenephenothiazine compound—and its application in anticancer drugs.

[0005] One of the technical solutions of the present invention is a novel polycyclic aromatic hydrocarbon derivative—2,6-di-tert-butylpyrene-indenephenothiazine compound, with the structural formula shown in formula (I):

[0006]

[0007] The second technical solution of the present invention is a method for preparing the above-mentioned 2,6-di-tert-butylpyrene-indenephenothiazine compound, comprising the following steps: using the 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenothiazine compound of formula (II) as raw material, and in the presence of palladium acetate, tricyclohexylphosphine tetrafluoroborate, and anhydrous potassium carbonate, with anhydrous dimethylacetamide as solvent, heating and reacting at 160°C for 24 h to obtain the compound;

[0008] Formula (II)

[0009]

[0010] Reaction equation:

[0011]

[0012] Furthermore, the molar ratio of the 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compound, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and anhydrous potassium carbonate is 1:0.2:0.4:6.

[0013] Furthermore, the heating reaction also includes water washing, dichloromethane extraction, drying and filtration, concentration and purification processes after the reaction is completed; the purification is carried out by silica gel column chromatography (the eluent is n-hexane: dichloromethane = 50 / 1, V / V).

[0014] Further, the preparation of the 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-4-yl)-10H-phenthiazine compound shown in formula (II) includes: using the 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound shown in formula (III) and 1-bromopyrene as raw materials, under the action of cuprous iodide, 18-crown ether-6, and anhydrous potassium carbonate, and anhydrous 1,2-dichlorobenzene as solvent, heating and reacting at 180°C for 48 h to obtain the product;

[0015] Formula (III)

[0016]

[0017] Reaction equation:

[0018]

[0019] Furthermore, the molar ratio of the 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound, 1-bromopyrene, cuprous iodide, 18-crown ether-6, and anhydrous potassium carbonate is 1:2:0.2:0.2:1.5.

[0020] Furthermore, the heating reaction also includes water washing, dichloromethane extraction, drying and filtration, concentration and purification processes after the reaction is completed; the purification is carried out by silica gel column chromatography (eluent is n-hexane).

[0021] The third technical solution of the present invention is the application of the above-mentioned 2,6-di-tert-butylpyrene-indenephenothiazine compound in the preparation of anticancer drugs.

[0022] Furthermore, the aforementioned anticancer drug is used to treat human cervical cancer HeLa cells.

[0023] Furthermore, the aforementioned anticancer drug is used to treat human lung cancer A549 cells.

[0024] Furthermore, the aforementioned anticancer drug is used to treat human prostate cancer PC-3 cells.

[0025] Furthermore, the aforementioned anticancer drug is used to treat human liver cancer HepG2 cells.

[0026] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0027] This invention provides a method for synthesizing a novel polycyclic aromatic hydrocarbon derivative—2,6-di-tert-butylpyrene-indenephenothiazine—and its application in anticancer drugs. The target compound exhibits significant selective inhibitory effects on various human tumor cell lines: specifically, on cervical cancer HeLa cells (ICVs). 50 =0.17μm), lung cancer A549 cells (IC 50 =0.3μm), prostate cancer PC-3 cells (IC 50 =0.42μm) exhibits strong inhibitory activity at the nanomolar level, with an IC50 of 0.42μm. 50 The values ​​were 109-fold, 173-fold, and 35-fold lower than those of the positive control drug cisplatin, respectively (corresponding to cisplatin IC50 values). 50 The values ​​were 18.58 μM, 51.92 μM, and 14.51 μM, respectively; the inhibitory activity against HepG2 liver cancer cells was relatively weak (IC50). 50 =10.79μm), its IC s0 The value was 1.8 times lower than that of the positive control drug cisplatin (corresponding to cisplatin IC50). 50 (Value: 18.91 μM). In addition to showing a high inhibition rate against the tested cancer cells, this compound also showed low cytotoxicity against normal cells, meeting the basic requirements of an excellent anticancer drug and demonstrating important application value in the field of novel anticancer drug development. Attached Figure Description

[0028] Figure 1 The hydrogen nuclear magnetic resonance spectrum of the 2,6-di-tert-butylpyrene-indenephenothiazine compound prepared in Example 1 of the present invention;

[0029] Figure 2 The carbon NMR spectrum of the 2,6-di-tert-butylpyrene-indenephenothiazine compound prepared in Example 1 of the present invention;

[0030] Figure 3 The single-crystal diffraction pattern is shown for the 2,6-di-tert-butylpyrene-indenephenothiazine compound prepared in Example 1 of this invention. Detailed Implementation

[0031] The present invention will now be described in detail with reference to specific embodiments.

[0032] Example 1

[0033] Synthesis of 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compounds

[0034] Take a 38 mL pressure-resistant reaction flask and add 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound (0.93 g, 2 mmol), 1-bromopyrene (1.12 g, 4 mmol), cuprous iodide (0.08 g, 0.4 mmol), 18-crown ether-6 (0.11 g, 0.4 mmol), and anhydrous potassium carbonate (0.41 g, 3 mmol) sequentially. Under argon protection, add anhydrous 1,2-dichlorobenzene (2 mL) and continuously bubble for 3 min, stirring at 180 °C for 48 h. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, concentrate the filtrate and dry under vacuum. The crude product is purified by silica gel column chromatography (eluent: n-hexane) to obtain the target product (0.87 g, pale yellow solid, yield 65%).

[0035] 1 H NMR (600MHz, CDCl3, 298K) δ8.02 (d, J=7.8Hz, 1H), 7.98 (d, J=8.4Hz, 1H), 7.92-7.90 (m, 2H), 7.88-7. 85 (m, 2H), 7.75-7.73 (m, 2H), 7.61-7.45 (m, 4H), 7.37-7.32 (m, 1H), 1.39 (s, 18H). HRMS (ESI) m / z: [M + ]calcd.For C 36 H 31 NSBr2, 667.0544; found, 667.0535.

[0036] Example 2

[0037] Synthesis of 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compounds

[0038] Take a 38 mL pressure-resistant reaction flask and add 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound (1.4 g, 3 mmol), 1-bromopyrene (1.68 g, 6 mmol), cuprous iodide (0.11 g, 0.6 mmol), 18-crown ether-6 (0.17 g, 0.6 mmol), and anhydrous potassium carbonate (0.62 g, 4.5 mmol) sequentially. Under argon protection, add anhydrous 1,2-dichlorobenzene (3 mL) and continuously bubble for 3 min, stirring at 180 °C for 48 h. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, concentrate the filtrate and dry under vacuum. The crude product is purified by silica gel column chromatography (eluent: n-hexane) to obtain the target product (1.31 g, pale yellow solid, yield 65%).

[0039] 1H NMR (600MHz, CDCl3, 298K) δ8.02 (d, J=7.8Hz, 1H), 7.98 (d, J=8.4Hz, 1H), 7.92-7.90 (m, 2H), 7.88-7. 85 (m, 2H), 7.75-7.73 (m, 2H), 7.61-7.45 (m, 4H), 7.37-7.32 (m, 1H), 1.39 (s, 18H). HRMS (ESI) m / z: [M + ]calcd.For C 36 H 31 NSBr2, 667.0544; found, 667.0535.

[0040] Example 3

[0041] Synthesis of 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compounds

[0042] Take a 38 mL pressure-resistant reaction flask and add 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound (1.87 g, 4 mmol), 1-bromopyrene (2.24 g, 8 mmol), cuprous iodide (0.15 g, 0.8 mmol), 18-crown ether-6 (0.22 g, 0.8 mmol), and anhydrous potassium carbonate (0.82 g, 6 mmol) sequentially. Under argon protection, add anhydrous 1,2-dichlorobenzene (4 mL) and continuously bubble for 3 min, stirring at 180 °C for 48 h. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, concentrate the filtrate and dry under vacuum. The crude product is purified by silica gel column chromatography (eluent: n-hexane) to obtain the target product (1.74 g, pale yellow solid, yield 65%).

[0043] 1 H NMR (600MHz, CDCl3, 298K) δ8.02 (d, J=7.8Hz, 1H), 7.98 (d, J=8.4Hz, 1H), 7.92-7.90 (m, 2H), 7.88-7. 85 (m, 2H), 7.75-7.73 (m, 2H), 7.61-7.45 (m, 4H), 7.37-7.32 (m, 1H), 1.39 (s, 18H). HRMS (ESI) m / z: [M + ]calcd.For C 36 H 31 NSBr2, 667.0544; found, 667.0535.

[0044] Example 4

[0045] Synthesis of 2,6-di-tert-butylpyrene-indenephenothiazine compounds

[0046] Take a 38 mL pressure-resistant reaction flask and add 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compound (0.4 g, 0.6 mmol), palladium acetate (0.03 g, 0.12 mmol), tricyclohexylphosphine tetrafluoroborate (0.09 g, 0.24 mmol), and anhydrous potassium carbonate (0.5 g, 3.6 mmol) sequentially. Under argon protection, add anhydrous dimethylacetamide (8 mL) and continuously bubble for 3 min, stirring at 160 °C for 24 h. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, concentrate the filtrate and dry under vacuum. The crude product is purified by silica gel column chromatography (eluent: hexane:dichloromethane = 50 / 1, V / V) to obtain the target product (0.22 g, yellow solid, yield 72%).

[0047] 1 H NMR (600MHz, CD2Cl2, 298K) δ8.51 (s, 1H), 8.23 ​​(s, 1H), 8.08 (d, J = 7.8Hz, 1H), 8.01 (d, J = 9.0Hz, 1H), 7.96-7.91 (m, 4H), 7.81 (d, J=9.0Hz, 1H), 7.19 (d, J=6.0Hz, 2H), 1.48 (s, 9H), 1.47 (s, 9H); 13 C NMR (150MHz, CDCl3 / CS2, 298K) δ147.6, 147.0, 132.8, 131.8, 129.5, 129.1, 128.4, 127.1, 126.7, 126.6, 126.1, 125.3, 125.0, 124.9, 123.5, 12 3.0, 122.6, 122.0, 121.9, 121.6, 121.3, 118.6, 118.0, 117.6, 116.6, 1 15.5, 115.3, 114.2, 35.5, 35.1, 32.1(3C), 31.6(3C); HRMS(ESI)m / z: [M + ]calcd.For C 36 H 29 NS, 507.2021; found, 507.2019.

[0048] Example 5

[0049] Synthesis of 2,6-di-tert-butylpyrene-indenephenothiazine compounds

[0050] Take a 38 mL pressure-resistant reaction flask and add 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compound (0.6 g, 0.9 mmol), palladium acetate (0.04 g, 0.18 mmol), tricyclohexylphosphine tetrafluoroborate (0.13 g, 0.36 mmol), and anhydrous potassium carbonate (0.75 g, 5.4 mmol) sequentially. Under argon protection, add anhydrous dimethylacetamide (12 mL) and continuously bubble for 3 min, stirring at 160 °C for 24 h. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, concentrate the filtrate and dry under vacuum. The crude product is purified by silica gel column chromatography (eluent: hexane:dichloromethane = 50 / 1, V / V) to obtain the target product (0.33 g, yellow solid, yield 72%).

[0051] 1 H NMR (600MHz, CD2Cl2, 298K) δ8.51 (s, 1H), 8.23 ​​(s, 1H), 8.08 (d, J = 7.8Hz, 1H), 8.01 (d, J = 9.0Hz, 1H), 7.96-7.91 (m, 4H), 7.81 (d, J=9.0Hz, 1H), 7.19 (d, J=6.0Hz, 2H), 1.48 (s, 9H), 1.47 (s, 9H); 13 C NMR (150MHz, CDCl3 / CS2, 298K) δ147.6, 147.0, 132.8, 131.8, 129.5, 129.1, 128.4, 127.1, 126.7, 126.6, 126.1, 125.3, 125.0, 124.9, 123.5, 12 3.0, 122.6, 122.0, 121.9, 121.6, 121.3, 118.6, 118.0, 117.6, 116.6, 1 15.5, 115.3, 114.2, 35.5, 35.1, 32.1(3C), 31.6(3C); HRMS(ESI)m / z: [M + ]calcd.For C 36 H 29 NS, 507.2021; found, 507.2019.

[0052] Example 6

[0053] Synthesis of 2,6-di-tert-butylpyrene-indenephenothiazine compounds

[0054] Take a 38 mL pressure-resistant reaction flask and add 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compound (0.8 g, 1.2 mmol), palladium acetate (0.06 g, 0.24 mmol), tricyclohexylphosphine tetrafluoroborate (0.18 g, 0.48 mmol), and anhydrous potassium carbonate (1 g, 7.2 mmol) sequentially. Under argon protection, add anhydrous dimethylacetamide (16 mL) and continuously bubble for 3 min, stirring at 160 °C for 24 h. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, concentrate the filtrate and dry under vacuum. The crude product is purified by silica gel column chromatography (eluent: hexane:dichloromethane = 50 / 1, V / V) to obtain the target product (0.44 g, yellow solid, yield 72%).

[0055] 1 H NMR (600MHz, CD2Cl2, 298K) δ8.51 (s, 1H), 8.23 ​​(s, 1H), 8.08 (d, J = 7.8Hz, 1H), 8.01 (d, J = 9.0Hz, 1H), 7.96-7.91 (m, 4H), 7.81 (d, J=9.0Hz, 1H), 7.19 (d, J=6.0Hz, 2H), 1.48 (s, 9H), 1.47 (s, 9H); 13 C NMR (150MHz, CDCl3 / CS2, 298K) δ147.6, 147.0, 132.8, 131.8, 129.5, 129.1, 128.4, 127.1, 126.7, 126.6, 126.1, 125.3, 125.0, 124.9, 123.5, 12 3.0, 122.6, 122.0, 121.9, 121.6, 121.3, 118.6, 118.0, 117.6, 116.6, 1 15.5, 115.3, 114.2, 35.5, 35.1, 32.1(3C), 31.6(3C); HRMS(ESI)m / z: [M + ]calcd.For C 36 H 29 NS, 507.2021; found, 507.2019.

[0056] Example 7

[0057] Evaluation Methods for the In Vitro Anticancer Activity of 2,6-Di-tert-butylpyrene-indenephenothiazine Compounds

[0058] This study used the MTT assay to evaluate the cytotoxic effects of the target compound on four human cancer cell lines (cervical cancer HeLa, lung cancer A549, prostate cancer PC-3, and liver cancer HepG2) and normal human umbilical vein endothelial cells (HUVECs). The specific experimental procedures are as follows:

[0059] Cell seeding and treatment

[0060] Prepare single-cell suspensions (density 10) from cells in the logarithmic growth phase. 5 Cells were seeded into 96-well plates (100 μL per well) and pre-cultured at 37°C in a 5% CO2 incubator for 24 h. After cell attachment, a series of test compound solutions (100 μL / well) were added, with 6 replicates for each concentration.

[0061] Drug effects and staining

[0062] After culturing for another 48 hours, add MTT staining solution (1 mg / mL, 100 μL) to each well and incubate for another 4 hours. Discard the supernatant, add 200 μL of DMSO to each well, and shake for 15 minutes.

[0063] Detection and Analysis

[0064] The absorbance (OD value) of each well was measured at 595 nm using an ELISA reader. A blank control group (containing only serum-free DMEM culture medium and DMSO) was set up. The cell inhibition rate was calculated according to formula (1):

[0065] Cell inhibition rate (%) = [1 - (OD)] 实验组 -OD 空白 ) / (OD 阴性对照 -OD 空白 )]×100%(1)

[0066] Data processing

[0067] Dose-response curves were fitted using Origin 9.0 software, and the half-maximal inhibitory concentration (IC50) was calculated. 50 The value was calculated. The experiment was repeated three times.

[0068] The results of the in vitro anticancer activity experiments of the 2,6-di-tert-butylpyrene-indenephenothiazine compound are shown in Table 1:

[0069] Table 1. Toxicity experiments of 2,6-di-tert-butylpyrene-indenephenothiazine compounds and positive control drug cisplatin (DDP) against HeLa, A549, PC-3, HepG2, and HUVEC (data in the table are IC50 values). 50 value):

[0070] compound Hela A549 PC-3 HepG2 HUVEC This patent 0.17 0.3 0.42 10.79 30.64 DDP 18.58 51.92 14.51 18.91 26.48

[0071] According to the experimental data in Table 1, the 2,6-di-tert-butylpyrene-indenephenothiazine compound synthesized in this patent exhibited differentiated inhibitory activity against the proliferation of HeLa, A549, PC-3, and HepG2 cancer cell lines. It showed potent inhibitory activity at the nanomolar level against HeLa, A549, and PC-3 cancer cells, with an IC50 value of [missing information]. 50 The values ​​were 109-fold, 173-fold, and 35-fold lower than those of the positive control drug cisplatin, respectively; its inhibitory activity against HepG2 hepatocellular carcinoma cells was relatively weak, and its IC50 value was lower than that of cisplatin. 50 The value was 1.8 times lower than that of the positive control drug cisplatin. In addition to showing a high inhibition rate against the tested cancer cells, this compound also showed low cytotoxicity to normal cells, meeting the basic requirements of an excellent anticancer drug and demonstrating important application value in the field of novel anticancer drug development.

Claims

1. A 2,6-di-tert-butylpyrene-indenephenothiazine compound, characterized in that, The structural formula is shown in equation (I):

2. The method for preparing the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 1, characterized in that, Includes the following steps: The compound 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine shown in formula (II) was prepared by heating at 160°C for 24 h in the presence of palladium acetate, tricyclohexylphosphine tetrafluoroborate and anhydrous potassium carbonate, with anhydrous dimethylacetamide as solvent. Formula (II) 3. The method for preparing the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 2, characterized in that, The preparation of the 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compound represented by formula (II) includes: using the 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound represented by formula (III) and 1-bromopyrene as raw materials, under the action of cuprous iodide, 18-crown ether-6, and anhydrous potassium carbonate, and with anhydrous 1,2-dichlorobenzene as solvent, the reaction is carried out at 180°C for 48 hours to obtain the compound. Formula (III) 4. The method for preparing the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 2, characterized in that, The molar ratio of the 1,9-dibromo-3,7-di-tert-butyl-10-(pyrene-1-yl)-10H-phenthiazine compound, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and anhydrous potassium carbonate is 1:0.2:0.4:

6.

5. The method for preparing the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 3, characterized in that, The molar ratio of the 1,9-dibromo-3,7-di-tert-butyl-10H-phenthiazine compound, 1-bromopyrene, cuprous iodide, 18-crown ether-6, and anhydrous potassium carbonate is 1:2:0.2:0.2:1.

5.

6. The use of a 2,6-di-tert-butylpyrene-indophenthiazide compound according to claim 1 in the preparation of an anticancer drug.

7. The use of the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 6 in the preparation of anticancer drugs, characterized in that, The aforementioned anticancer drug is used to treat human cervical cancer HeLa cells.

8. The use of the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 6 in the preparation of anticancer drugs, characterized in that, The aforementioned anticancer drug is used to treat human lung cancer A549 cells.

9. The use of the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 6 in the preparation of anticancer drugs, characterized in that, The aforementioned anticancer drug is used to treat human prostate cancer PC-3 cells.

10. The use of the 2,6-di-tert-butylpyrene-indenephenothiazine compound according to claim 6 in the preparation of anticancer drugs, characterized in that, The aforementioned anticancer drug is used to treat human liver cancer HepG2 cells.

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