4, 8-di-tert-butyl-1, 6-dithiaazacyclopentylnaphtho acenaphthene compound as well as preparation method and application thereof

Abstract

The invention discloses a novel anti-tumor lead compound, namely 4, 8-di-tert-butyl-1, 6-dithiaazacyclopentylnaphtho acenaphthene as well as a preparation method and application of the novel anti-tumor lead compound. The synthesis route is simple and convenient to operate. In-vitro anti-tumor activity evaluation shows that the compound shows remarkable selective inhibitory activity on various human tumor cell lines, and ICs0 values of the compound are 0.85 mu M of breast cancer MCF-7 cells, 2.13 mu M of prostate cancer PC-3 cells, 6.11 mu M of liver cancer HepG2 cells, 9.23 mu M of non-small cell lung cancer A549 cells and 13.9 mu M of cervical cancer Hela cells respectively. The inhibitory activity of the compound is obviously superior to that of a clinical common chemotherapeutic drug cis-platinum. Preliminary toxicity experiments show that the compound has low cytotoxicity. The compound shows excellent anti-tumor activity and good development potential, and provides an important lead compound structure basis for research and development of novel high-efficiency low-toxicity anti-tumor drugs.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to a 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenaphenacenaphthylene compound, a preparation method thereof, and medical applications thereof. Background Art

[0002] Phenothiazine is a butterfly-shaped aromatic heterocyclic compound formed by the fusion of a six-membered nitrogen-sulfur heterocycle and two benzene rings. Due to its unique electronic structure and modifiable properties, phenothiazine and its derivatives have shown important application value in the fields of functional material development, pharmaceutical research and development, and petrochemical industry. In recent years, the research on the construction of phenothiazine derivatives through chemical modification has attracted much attention. Its structural modification strategies mainly include: (1) heterocyclic modification: introduction of nitrogen atom substituents, oxidation of sulfur atoms (sulfoxide / sulfone); (2) aromatic ring modification: modification of benzene ring substituents, replacement of benzene rings with homologous / heterologous aromatic rings to construct polyaromatic ring systems or nitrogen heterocyclic structures; (3) π conjugated system expansion: extension of the molecular planar conjugated structure through polycyclic fusion strategies. These modification strategies have successfully prepared many functional molecules with novel structures and unique properties. [Zhou, J., Mao, L., Wu, M.-X., Peng, Z., Yang, Y., Zhou, M., Zhao, X.-L., Shi, X., Yang, H.-B. Chem. Sci., 2022, 13, 5252-5260.]

[0003] While ring fusion strategies have made significant progress in the synthesis of phenothiazine derivatives, current research focuses primarily on molecular design and physical property characterization, with insufficient systematic exploration of potential applications, limiting the practical application value of this approach. [Wu, J., Zhang, G. Angew. Chem. Int. Ed., 2022, 61, e202208061.] Notably, the intrinsic properties of phenothiazine-based materials can be precisely optimized through the regulation of π-conjugated systems, thereby adapting them to specific application needs.

[0004] In the field of biomedicine, malignant tumors are a major disease that threatens human health, and their prevention and treatment needs are particularly urgent. According to the 2022 global cancer statistics of the International Agency for Research on Cancer (IARC), there were 20 million new cancer cases and approximately 9.7 million deaths in that year, among which breast cancer, lung cancer, prostate cancer, and cervical cancer ranked at the top in terms of incidence and mortality. Although currently commonly used clinical chemotherapy drugs such as cisplatin, paclitaxel, 5-fluorouracil, and cyclophosphamide have broad-spectrum anticancer activity, they generally have significant toxic side effects and drug resistance, which seriously restrict their long-term efficacy. [Bray, F., Laversanne, M., Sung, H., Ferlay, J., Siegel, RL, Soerjomataram, I., Jemal, A.CA. Cancer. J. Clin., 2024, 74, 229-263.] Therefore, the development of new anti-tumor molecules with high efficiency and low toxicity has become a research direction that urgently needs breakthroughs.

[0005] This study designed and synthesized novel phenothiazine derivatives based on a ring fusion strategy and systematically evaluated their bioactivity against common cancer cells. By expanding the π-conjugated phenothiazine system to manipulate the molecular electronic properties and combining structure-activity relationship analysis, the study aims to provide a theoretical basis and practical reference for the development of novel anti-tumor lead compounds. Summary of the Invention

[0006] Based on the above content, the present invention provides a 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound, a preparation method and application thereof.

[0007] One of the technical solutions of the present invention is a 4,8-di-tert-butyl-1,6-dithiazacyclopenta-naphthoacenaphthylene compound, the structural formula of which is shown in formula (I):

[0008]

[0009] The second technical solution of the present invention is a method for preparing the above-mentioned 4,8-di-tert-butyl-1,6-dithiazacyclopenta-naphthoacenaphthylene compound, comprising the following steps: using a 10-(benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound represented by formula (II) as a raw material, in the presence of palladium acetate, tricyclohexylphosphine tetrafluoroborate, and anhydrous potassium carbonate, and using anhydrous dimethylacetamide as a solvent, heating the reaction at 160°C for 24 hours to obtain the obtained compound;

[0010] Structural formula (II)

[0011]

[0012] Reaction equation:

[0013]

[0014] Furthermore, the molar ratio of the 10-(benzo[b]thiophene-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and anhydrous potassium carbonate is 1:0.2:0.4:6.

[0015] Furthermore, the heating reaction also includes water washing, dichloromethane extraction, drying filtration, concentration, and purification processes after the reaction is completed; the purification is performed by silica gel column chromatography (eluent is n-hexane: dichloromethane = 50 / 1, V / V).

[0016] Furthermore, the preparation of the 10-(benzo[b]thiophene-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound represented by formula (II) includes: using the 1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound represented by formula (III) and 4-bromobenzo[b]thiophene as raw materials, in the presence of cuprous iodide, 18-crown ether-6, and anhydrous potassium carbonate, and using anhydrous 1,2-dichlorobenzene as a solvent, heating the reaction at 180°C for 48 hours to obtain the compound;

[0017] Formula (III)

[0018]

[0019] Reaction equation:

[0020]

[0021] Furthermore, the heating reaction also includes water washing, dichloromethane extraction, drying and filtering, concentration, and purification processes after the reaction is completed; the purification is performed by silica gel column chromatography separation and purification (the eluent is n-hexane).

[0022] The third technical solution of the present invention is the use of the above-mentioned 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound in the preparation of anti-tumor drugs.

[0023] Furthermore, the anti-tumor drug is used to treat human breast cancer (MCF-7).

[0024] Furthermore, the anti-tumor drug is used to treat human prostate cancer (PC-3).

[0025] Furthermore, the anti-tumor drug is used to treat human liver cancer (HepG2).

[0026] Furthermore, the anti-tumor drug is used to treat human non-small cell lung cancer (A549).

[0027] Furthermore, the anti-tumor drug is used to treat human cervical cancer (Hela).

[0028] Compared with the prior art, the present invention has the following beneficial effects:

[0029] The present invention designs and synthesizes a series of novel phenothiazine derivatives based on the ring fusion strategy, and systematically evaluates their biological activities against common cancer cells. The 4,8-di-tert-butyl-1,6-dithia-azacyclopenta-naphthoacenaphthylene compound prepared by the present invention exhibits significant selective inhibitory effects on a variety of human tumor cell lines: the half inhibitory concentration (IC50) is 2.37 for breast cancer MCF-7 cells, prostate cancer PC-3 cells, liver cancer HepG2 cells, non-small cell lung cancer A549 cells, and cervical cancer Hela cells. 50 ) were 0.85μM, 2.13μM, 6.11μM, 9.23μM, and 13.9μM, respectively. Compared with the commonly used clinical chemotherapy drug cisplatin, the compound showed significantly enhanced inhibitory activity against the above-mentioned tumor cell lines. In addition, preliminary toxicity experiments showed that it has low cytotoxicity, showing good potential for anti-tumor drug development. This research result provides an important lead compound structural foundation for the development of new, highly effective, and low-toxic anti-tumor drugs. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 This is a hydrogen nuclear magnetic resonance spectrum of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound prepared in Example 1 of the present invention;

[0031] Figure 2 This is the carbon nuclear magnetic resonance spectrum of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound prepared in Example 1 of the present invention. DETAILED DESCRIPTION

[0032] The present invention is described in detail below with reference to specific embodiments.

[0033] Example 1

[0034] Synthesis of 10-(Benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine

[0035] To a 38 mL pressure-resistant reaction flask, add 1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine (0.93 g, 2 mmol), 4-bromobenzo[b]thiophene (0.85 g, 4 mmol), cuprous iodide (0.08 g, 0.4 mmol), 18-crown-6 (0.11 g, 0.4 mmol), and anhydrous potassium carbonate (0.41 g, 3 mmol). Under argon, add anhydrous 1,2-dichlorobenzene (2 mL) and continue bubbling for 3 minutes. Stir at 180°C for 48 hours. After the reaction is complete, cool to room temperature, add dichloromethane (50 mL), wash three times with water, dry over anhydrous magnesium sulfate, filter, and concentrate the filtrate to dryness. The crude product is purified by silica gel column chromatography (eluent: n-hexane) to obtain the desired product (0.67 g, pale yellow solid, 56% yield).

[0036] 1 H NMR (600MHz, CDCl3, 298K) δ7.93-7.68 (m, 2H), 7.61-7.43 (m, 3H), 7.15 (t, J=8.4Hz, 1H), 7.13-7.00 (m, 1H), 6.67 (t, J=7.8Hz, 1H), 5.92-5.86 (m, 1H), 1.36 (s, 18H). HRMS(ESI)m / z: HRMS(ESI)m / z: [M+H + ]calcd.For C 28 H 28 NS2Br2, 600.0030; found, 600.0021.

[0037] Example 2

[0038] Synthesis of 10-(Benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine

[0039] To a 38 mL pressure-resistant reaction flask, 1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine (1.4 g, 3 mmol), 4-bromobenzo[b]thiophene (1.28 g, 6 mmol), cuprous iodide (0.12 g, 0.6 mmol), 18-crown-6 (0.17 g, 0.6 mmol), and anhydrous potassium carbonate (0.62 g, 4.5 mmol) were added in sequence. Under argon, anhydrous 1,2-dichlorobenzene (3 mL) was added and bubbled continuously for 3 minutes. The mixture was stirred at 180°C for 48 hours. After the reaction, the mixture was cooled to room temperature, and dichloromethane (50 mL) was added. The mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to dryness. The crude product was purified by silica gel column chromatography (eluent: n-hexane) to obtain the desired product (1 g, pale yellow solid, 56% yield).

[0040] 1 H NMR (600MHz, CDCl3, 298K) δ7.93-7.68 (m, 2H), 7.61-7.43 (m, 3H), 7.15 (t, J=8.4Hz, 1H), 7.13-7.00 (m, 1H), 6.67 (t, J=7.8Hz, 1H), 5.92-5.86 (m, 1H), 1.36 (s, 18H). HRMS(ESI)m / z: HRMS(ESI)m / z: [M+H + ]calcd.For C 28 H 28 NS2Br2, 600.0030; found, 600.0021.

[0041] Example 3

[0042] Synthesis of 10-(Benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine

[0043] To a 38 mL pressure-resistant reaction flask, 1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine (1.86 g, 4 mmol), 4-bromobenzo[b]thiophene (1.7 g, 8 mmol), cuprous iodide (0.16 g, 0.8 mmol), 18-crown-6 (0.22 g, 0.8 mmol), and anhydrous potassium carbonate (0.82 g, 6 mmol) were added in sequence. Under argon, anhydrous 1,2-dichlorobenzene (4 mL) was added and bubbled continuously for 3 minutes. The mixture was stirred at 180°C for 48 hours. After the reaction, the mixture was cooled to room temperature, and dichloromethane (50 mL) was added. The mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to dryness. The crude product was purified by silica gel column chromatography (eluent: n-hexane) to obtain the desired product (1.34 g, light yellow solid, 56% yield).

[0044] 1 H NMR (600MHz, CDCl3, 298K) δ7.93-7.68 (m, 2H), 7.61-7.43 (m, 3H), 7.15 (t, J=8.4Hz, 1H), 7.13-7.00 (m, 1H), 6.67 (t, J=7.8Hz, 1H), 5.92-5.86 (m, 1H), 1.36 (s, 18H). HRMS(ESI)m / z: HRMS(ESI)m / z: [M+H + ]calcd.For C 28 H 28 NS2Br2, 600.0030; found, 600.0021.

[0045] Example 4

[0046] Synthesis of 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenaphenacenaphthylene

[0047] In a 38 mL pressure-resistant reaction flask, 10-(benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine (0.4 g, 0.67 mmol), palladium acetate (0.03 g, 0.13 mmol), tricyclohexylphosphine tetrafluoroborate (0.1 g, 0.26 mmol), and anhydrous potassium carbonate (0.55 g, 4 mmol) were added in sequence. Under argon, anhydrous dimethylacetamide (8 mL) was added and bubbled continuously for 3 minutes. The mixture was stirred at 160°C for 24 hours. After the reaction, the mixture was cooled to room temperature, and dichloromethane (50 mL) was added. The mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to dryness. The crude product was purified by silica gel column chromatography (eluent: n-hexane:dichloromethane = 50 / 1, v / v) to obtain the desired product (0.12 g, yellow solid, 41% yield).

[0048] 1 H NMR (600MHz, CDCl3, 298K) δ7.82 (d, J=8.4Hz, 1H), 7.67 (d, J=1.2Hz, 1H), 7.54 (d, J=8.4Hz, 1H), 7.51 ( d, J=1.8Hz, 1H), 7.41 (s, 1H), 7.06 (d, J=1.8Hz, 1H), 7.04 (d, J=1.2Hz, 1H), 1.42 (s, 9H), 1.37 (s, 9H); 13 C NMR (150MHz, CDCl3, 298K) δ148.0, 147.2, 134.8, 132.2, 129.9, 127.7, 127.6, 127.3, 122.9, 122.8, 122.1, 120. 4, 120.3, 120.2, 116.8, 116.7, 115.6, 115.4, 114.8, 113.4, 35.5, 35.0, 32.1(3C), 31.5(3C); HRMS(ESI) m / z: [M + ]calcd.For C 28 H 25 NS2, 439.1428; found, 439.1431.

[0049] Example 5

[0050] Synthesis of 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenaphenacenaphthylene

[0051] In a 38 mL pressure-resistant reaction flask, 10-(benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine (0.6 g, 1 mmol), palladium acetate (0.05 g, 0.2 mmol), tricyclohexylphosphine tetrafluoroborate (0.15 g, 0.39 mmol), and anhydrous potassium carbonate (0.83 g, 6 mmol) were added in sequence. Under argon, anhydrous dimethylacetamide (12 mL) was added and bubbled continuously for 3 minutes. The mixture was stirred at 160°C for 24 hours. After the reaction, the mixture was cooled to room temperature, and dichloromethane (50 mL) was added. The mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to dryness. The crude product was purified by silica gel column chromatography (eluent: n-hexane:dichloromethane = 50 / 1, v / v) to obtain the desired product (0.18 g, yellow solid, 41% yield).

[0052] 1 H NMR (600MHz, CDCl3, 298K) δ7.82 (d, J=8.4Hz, 1H), 7.67 (d, J=1.2Hz, 1H), 7.54 (d, J=8.4Hz, 1H), 7.51 ( d, J=1.8Hz, 1H), 7.41 (s, 1H), 7.06 (d, J=1.8Hz, 1H), 7.04 (d, J=1.2Hz, 1H), 1.42 (s, 9H), 1.37 (s, 9H); 13 C NMR (150MHz, CDCl3, 298K) δ148.0, 147.2, 134.8, 132.2, 129.9, 127.7, 127.6, 127.3, 122.9, 122.8, 122.1, 120. 4, 120.3, 120.2, 116.8, 116.7, 115.6, 115.4, 114.8, 113.4, 35.5, 35.0, 32.1(3C), 31.5(3C); HRMS(ESI) m / z: [M + ]calcd.For C 28 H 25 NS2, 439.1428; found, 439.1431.

[0053] Example 6

[0054] Synthesis of 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenaphenacenaphthylene

[0055] In a 38 mL pressure-resistant reaction flask, 10-(benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine (0.8 g, 1.34 mmol), palladium acetate (0.06 g, 0.26 mmol), tricyclohexylphosphine tetrafluoroborate (0.2 g, 0.52 mmol), and anhydrous potassium carbonate (1.1 g, 8 mmol) were added in sequence. Under argon, anhydrous dimethylacetamide (16 mL) was added and bubbled continuously for 3 minutes. The mixture was stirred at 160°C for 24 hours. After the reaction, the mixture was cooled to room temperature, and dichloromethane (50 mL) was added. The mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to dryness. The crude product was purified by silica gel column chromatography (eluent: n-hexane:dichloromethane = 50 / 1, v / v) to obtain the desired product (0.24 g, yellow solid, 41% yield).

[0056] 1 H NMR (600MHz, CDCl3, 298K) δ7.82 (d, J=8.4Hz, 1H), 7.67 (d, J=1.2Hz, 1H), 7.54 (d, J=8.4Hz, 1H), 7.51 ( d, J=1.8Hz, 1H), 7.41 (s, 1H), 7.06 (d, J=1.8Hz, 1H), 7.04 (d, J=1.2Hz, 1H), 1.42 (s, 9H), 1.37 (s, 9H); 13 C NMR (150MHz, CDCl3, 298K) δ148.0, 147.2, 134.8, 132.2, 129.9, 127.7, 127.6, 127.3, 122.9, 122.8, 122.1, 120. 4, 120.3, 120.2, 116.8, 116.7, 115.6, 115.4, 114.8, 113.4, 35.5, 35.0, 32.1(3C), 31.5(3C); HRMS(ESI) m / z: [M + ]calcd.For C 28 H 25 NS2, 439.1428; found, 439.1431.

[0057] Example 7

[0058] The anti-tumor activity of 4,8-di-tert-butyl-1,6-dithiazolyl naphthacenaphthylene compound on human breast cancer MCF-7 cells, human prostate cancer PC-3 cells, human liver cancer HepG2 cells, human non-small cell lung cancer A549 cells, and human cervical cancer Hela cells was tested. The specific experimental methods are as follows:

[0059] The MTT thiazolyl blue colorimetric method was used to study the cytotoxic activity of 4,8-di-tert-butyl-1,6-dithiazolyl naphthacenaphthylene compounds on human breast cancer MCF-7 cells, human prostate cancer PC-3 cells, human liver cancer HepG2 cells, human non-small cell lung cancer A549 cells, human cervical cancer Hela cells and normal human umbilical vein endothelial cells (HUVEC). The cells to be tested in the logarithmic growth phase were prepared into 10 5 A single cell suspension of 100 μL / mL was inoculated on a 96-well culture plate, with 100 μL per well. After culturing for 24 h in a 37°C incubator with a volume fraction of 5% carbon dioxide and saturated humidity, 100 μL of the sample to be tested at different concentrations was added to the culture plate, with 6 replicates for each concentration. After culturing for 48 h, 100 μL (1 mg / mL) of MTT staining solution was added to each well, and the plate was incubated for another 4 h in the incubator. The supernatant was removed, and then 200 μL of the sample to be tested was added to each well. DMSO was fully shaken for 15 minutes, and the OD sample value was measured at a wavelength of 595 nm on a microplate reader. The blank group of the experiment was 100 μL of serum-free DMEM culture medium with DMSO reagent added instead of the sample. The absorbance value at this time was the OD blank value. The cell inhibition rate of 4,8-di-tert-butyl-1,6-dithiazolyl-naphthoacenaphthylene compound on human breast cancer MCF-7 cells, human prostate cancer PC-3 cells, human liver cancer HepG2 cells, human non-small cell lung cancer A549 cells, human cervical cancer Hela cells and normal cells human umbilical vein endothelial cells (HUVEC) was calculated by formula (1). Finally, the IC 50 .

[0060] m=1-n=1-OD 样 / OD 空白 (1)

[0061] m: inhibition rate n: cell survival rate

[0062] The anti-tumor activity test results of 4,8-di-tert-butyl-1,6-dithiazolyl naphthacenaphthylene compound on human breast cancer MCF-7 cells, human prostate cancer PC-3 cells, human liver cancer HepG2 cells, human non-small cell lung cancer A549 cells, and human cervical cancer Hela cells are shown in Table 1:

[0063] Table 1. Cytotoxicity of 4,8-di-tert-butyl-1,6-dithiazolyl-naphthoacenaphthylene compounds and the positive control drug cisplatin on human breast cancer MCF-7 cells, human prostate cancer PC-3 cells, human liver cancer HepG2 cells, human non-small cell lung cancer A549 cells, human cervical cancer Hela cells, and normal human umbilical vein endothelial cells (HUVEC) (data in the table are IC 50 value):

[0064] Compound MCF-7 PC-3 HepG2 A549 Hela HUVEC This patent 0.85 2.13 6.11 9.23 13.9 36.8 Cisplatin 39.88 14.51 18.91 51.92 18.58 26.48

[0065] As shown in Table 1, the 4,8-di-tert-butyl-1,6-dithiazolinone naphthacenaphthylene compound synthesized in this patent showed different degrees of inhibitory effects on human breast cancer MCF-7 cells, human prostate cancer PC-3 cells, human liver cancer HepG2 cells, human non-small cell lung cancer A549 cells, and human cervical cancer Hela cells. The effects were significant and better than the positive control drug cisplatin, and the toxicity was relatively low, showing good potential for anti-tumor drug development.

Claims

1. A 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound, characterized in that: The structural formula is shown in formula (I):

2. The method for preparing 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 1, wherein: The following steps are involved: The 10-(benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound represented by formula (II) is used as a raw material, in the presence of palladium acetate, tricyclohexylphosphine tetrafluoroborate, anhydrous potassium carbonate, and anhydrous dimethylacetamide as a solvent, and the reaction is heated at 160°C for 24 hours to obtain the product. Structural formula (II) 3. The method for preparing 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 2, wherein: The preparation of the 10-(benzo[b]thiophen-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound represented by formula (II) comprises: using the 1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound represented by formula (III) and 4-bromobenzo[b]thiophene as raw materials, in the presence of cuprous iodide, 18-crown ether, and anhydrous potassium carbonate, using anhydrous 1,2-dichlorobenzene as a solvent, and heating the mixture at 180° C. for 48 hours to obtain the obtained compound; Formula (III) 4. The method for preparing 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 2, wherein: The molar ratio of the 10-(benzo[b]thiophene-4-yl)-1,9-dibromo-3,7-di-tert-butyl-10H-phenothiazine compound, palladium acetate, tricyclohexylphosphine tetrafluoroborate, and anhydrous potassium carbonate is 1:0.2:0.4:

6.

5. Use of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 1 in the preparation of anti-tumor drugs.

6. Use of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 5 in the preparation of anti-tumor drugs, characterized in that: The anti-tumor drug is used for treating human breast cancer (MCF-7).

7. Use of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 5 in the preparation of anti-tumor drugs, characterized in that: The anti-tumor drug is used for treating human prostate cancer (PC-3).

8. Use of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 5 in the preparation of anti-tumor drugs, characterized in that: The anti-tumor drug is used for treating human liver cancer (HepG2).

9. Use of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 5 in the preparation of anti-tumor drugs, characterized in that: The anti-tumor drug is used to treat human non-small cell lung cancer (A549).

10. Use of the 4,8-di-tert-butyl-1,6-dithiazacyclopentaphenacenaphthylene compound according to claim 5 in the preparation of anti-tumor drugs, characterized in that: The anti-tumor drug is used for treating human cervical cancer (Hela).

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