Preparation and anti-tumor application of 9, 10-anthraquinone-(3, 5-disubstituted salicylaldehyde) Schiff base dibutyltin complex

Abstract

The invention discloses a 9, 10-anthraquinone-(3, 5-disubstituted salicylaldehyde) Schiff base dibutyltin complex, which is a compound with the following structural formula (I): # imgabs0 #, therefore, the inventor also establishes a corresponding preparation method, that is, 2-amino-3-hydroxy anthraquinone, 3, 5-disubstituted salicylaldehyde and dibutyltin oxide are used as raw materials, absolute methanol is used as a solvent, and the 9, 10-anthraquinone-(3, 5-disubstituted salicylaldehyde) Schiff base dibutyltin complex is prepared by reacting the raw materials with the absolute methanol to obtain the 9, 10-anthraquinone-(3, 5-disubstituted salicylaldehyde) Schiff base dibutyltin complex. And the reaction is completed under the condition of heating reflux. An in-vitro anticancer activity research shows that the 9, 10-anthraquinone-(3, 5-disubstituted salicylaldehyde) Schiff base dibutyltin complex has good inhibitory activity on human lung cancer cells, human liver cancer cells, human breast cancer cells and human oral cancer, and the in-vitro anticancer activity of the 9, 10-anthraquinone-(3, 5-disubstituted salicylaldehyde) Schiff base dibutyltin complex is remarkably superior to that of a classic metal anticancer drug cis-platinum. Therefore, the compound has potential application value in research and development of anti-cancer drugs for human lung cancer, human liver cancer, human breast cancer and human oral cancer. In conclusion, the anthraquinone dibutyltin complex is good in anticancer activity, low in cost and simple in preparation method, and a new way is provided for developing new anticancer drugs.

Description

Technical Field

[0001] The present invention belongs to the technical field of anthraquinone derivatives, and particularly relates to the preparation and anti-tumor application of a 9,10-anthraquinone-(3,5-disubstituted salicylaldehyde) Schiff base dibutyltin complex. Background Art

[0002] Anthraquinone anti-tumor drugs are one of the chemotherapy drugs widely used in current clinical treatment. These drugs have a common parent nucleus structure (9,10-anthraquinone skeleton structure). Anthraquinone anti-tumor drugs interfere with the metabolic process of tumor cells and inhibit the proliferation of tumor cells, thereby achieving the purpose of treating tumors. In clinical applications, anthraquinone anti-tumor drugs are widely used in the treatment of various types of tumors. In recent decades, researchers have designed and synthesized a large number of new 9,10-anthraquinone derivatives based on the 9,10-anthraquinone parent nucleus structure, and found that 9,10-anthraquinone derivatives have good inhibitory effects on the proliferation of various cancer cells. Therefore, designing and synthesizing new 9,10-anthraquinone derivatives with excellent anti-cancer activity has become an important research direction for the development of anthraquinone anti-cancer drugs.

[0003] Organotin is a unique organometallic compound formed by the direct binding of Sn atoms and C atoms. It has significant biological activity and has attracted much attention due to its cytotoxic effect and strong DNA binding ability. These compounds can inhibit cell proliferation and induce apoptosis, showing potential drug treatment value in cancer chemotherapy. The exertion of its biological activity is affected by various parameters, including the number of tin atoms, the nature of the ligand, and the coordination number, etc. In particular, the organic groups attached to the organotin atom and the ligands participating in coordination play a decisive role in the biological activity of organotin compounds. Therefore, selecting organic ligands with good biological activity to coordinate with the tin atoms in organotin has become the research focus of scientific researchers.

[0004] After investigation, the reports on the application of anti-cancer drugs involving anthraquinone derivatives or organotin compounds are as follows:

[0005] The Chinese patent "An Anthraquinone Compound, Preparation Method and Application" (Patent No. 2021108311403, Publication Date: February 3, 2023) discloses an anthraquinone compound and its preparation method, and this compound has good application prospects in the field of biological activity and can be used as a potential anti-cancer drug and a new type of topoisomerase inhibitor drug.

[0006] The Chinese patent "Preparation and Application of an Anthraquinone Compound Inducing Paraptosis in Hepatocarcinoma Cells" (Patent No. 2018105721353, Publication Date: September 28, 2018) discloses the preparation and application of an anthraquinone compound that can induce paraptosis in hepatocarcinoma cells, and it is found that this anthraquinone compound can kill tumor cells by inducing paraptosis, showing good prospects for application as an anti-tumor drug.

[0007] The Chinese patent application "2-Hydroxy-N-(2-hydroxybenzoyl)benzohydrazide Dibutyltin Complex, Preparation Method and Application" (Patent Application No. 2012103923480, Publication Date: January 30, 2013) discloses a 2-hydroxy-N-(2-hydroxybenzoyl)benzohydrazide dibutyltin complex, which has the characteristics of high anti-cancer activity, good liposolubility, low cost, and simple preparation method.

[0008] The Chinese patent "A 2-Oxo-2-phenylacetic Acid Salicylhydrazone Dibutyltin Complex, Its Preparation Method and Application" (Patent No. 2015107777398, Publication Date: December 30, 2015) discloses the preparation method of a 2-oxo-2-phenylacetic acid salicylhydrazone dibutyltin complex and its application in the preparation of anti-cancer drugs.

[0009] The literature (J. Med. Chem. 2024, 67: 4624 - 4640.) reports that a new class of anthraquinone compounds has strong cytotoxicity against various tumor cells and can insert into AT-rich DNA base pairs, thereby achieving selective cleavage of T and A bases.

[0010] The literature (Eur. J. Med. Chem. 2025, 281: 117013.) reports a new class of heteroarene-fused anthraquinone compounds with high anti-cancer activity, and the synthesized compounds interact with DNA double strands and inhibit topoisomerase.

[0011] The literature (Pharmaceuticals, 2024, 17(12): 1717.) reports a class of complexes of anthraquinone with copper or iron, which have high cytotoxic effects on tumor cells and can reduce the iron-induced lipid peroxidation rate, and are expected to be further evaluated and applied as tumor chemotherapy drugs.

[0012] The literature (Future Medicinal Chemistry, 2020, 12(2), 111 - 126.) reports that a class of rhein derivatives can induce DNA damage in human lung cancer A549 cells and enhance their radiosensitivity.

[0013] The literature (ACS Med.Chem.Lett. 2019, 10: 732 - 736) reported a new class of anthraquinone derivatives that can induce tumor cell death through paraptosis.

[0014] While modifying based on the 9,10 - anthraquinone skeleton structure, researchers are almost all keen on synthesizing small - molecule organic compounds. However, there are few reports on organic tin complexes synthesized based on the 9,10 - anthraquinone skeleton structure as ligands that can significantly improve the anti - cancer activity of anthraquinone. Summary of the Invention

[0015] The technical problem to be solved by the present invention is to provide the preparation and anti - tumor application of 9,10 - anthraquinone - (3,5 - disubstituted salicylaldehyde) Schiff base dibutyltin complex.

[0016] To solve the above - mentioned technical problem, the present invention adopts the following technical solutions:

[0017] Therefore, the present invention selects 2 - amino - 3 - hydroxy - 9,10 - anthraquinone, 3,5 - disubstituted salicylaldehyde and dibutyltin oxide to react under certain conditions, and synthesizes 9,10 - anthraquinone - (3,5 - disubstituted salicylaldehyde) Schiff base dibutyltin complex which has certain inhibitory activities against human lung cancer cells (A549), human liver cancer cells (HepG2), human breast cancer cells (MCF - 7) and human oral cancer cells (CAL - 27). Moreover, its in vitro anti - cancer activity is significantly better than that of the classical metal - based anti - cancer drug cisplatin, providing a new way for the development of anti - cancer drugs.

[0018] The 9,10 - anthraquinone - (3,5 - disubstituted salicylaldehyde) Schiff base dibutyltin complex is a compound of the following structural formula (I):

[0019]

[0020] Wherein, R 1 or R 2 is - Cl, - Br, - C(CH3)3.

[0021] When R 1 and R 2 are both - Br, this complex is A2, its crystal is monoclinic system, space group α = 90°, β = 99.516(2)°, γ = 90°, Z = 24, Dc = 1.743Mg·m -3 , F(000) = 8640.0; the tin atom in the molecule has a five - coordinated trigonal bipyramidal configuration;

[0022] When R 1 is -Br and R 2 is -Cl, the complex is A4, and its crystal is triclinic system, space group P-1, α = 62.2300(10)°, β = 80.2890(10)°, γ = 80.0470(10)°, Z = 6, Dc = 1.685 Mg·m -3 , F(000) = 2052.0; the tin atom in the molecule has a pentacoordinated trigonal bipyramidal configuration.

[0023] Application of anthraquinone dibutyltin complex in the preparation of anti-tumor drugs.

[0024] The tumor is lung cancer, liver cancer, breast cancer or oral cancer.

[0025] Lung cancer, liver cancer, breast cancer and oral cancer originate from human lung cancer cell A549, human liver cancer cell HepG2, human breast cancer cell MDA-MB-231 and human oral cancer cell CAL-27 respectively.

[0026] Preparation method of anthraquinone dibutyltin complex, using 2-amino-3-hydroxyanthraquinone, 3,5-disubstituted salicylaldehyde and dibutyltin oxide as raw materials, using anhydrous methanol as solvent, and reacting under the condition of heating and refluxing.

[0027] The 3,5-disubstituted salicylaldehyde is 3,5-dichlorosalicylaldehyde, 3,5-dibromosalicylaldehyde, 3,5-di-tert-butylsalicylaldehyde, 3-bromo-5-chlorosalicylaldehyde.

[0028] The molar ratio of 2-amino-3-hydroxyanthraquinone, 3,5-disubstituted salicylaldehyde and dibutyltin oxide is 1:1:1.

[0029] Preparation method: Add 1 mmol of 2-amino-3-hydroxyanthraquinone, 1 mmol of 3,5-disubstituted salicylaldehyde, 1 mmol of dibutyltin oxide and 30 ml of anhydrous methanol as solvent into a flask, react for 8 h under the condition of heating and refluxing, cool, filter, and control the solvent to volatilize and crystallize at room temperature to obtain the product.

[0030] Through in-depth research on 9,10-anthraquinone skeleton structure compounds, the inventors designed and prepared a 9,10-anthraquinone-(3,5-disubstituted salicylaldehyde) Schiff base dibutyltin complex, which is a compound of the following structural formula (I):

[0031]

[0032] Among them, R 1 or R 2They are -Cl, -Br, -C(CH3)3. The tin atom in the compound molecule has a trigonal bipyramidal configuration with five coordination sites.

[0033] Accordingly, the inventors also established a corresponding preparation method, that is, using 2-amino-3-hydroxyanthraquinone, 3,5-disubstituted salicylaldehyde and dibutyltin oxide as raw materials, anhydrous methanol as the solvent, and reacting under the condition of heating and reflux. The in vitro anti-cancer activity study shows that the 9,10-anthraquinone-(3,5-disubstituted salicylaldehyde) Schiff base dibutyltin complex of the present invention has good inhibitory activity against human lung cancer cells, human liver cancer cells, human breast cancer cells and human oral cancer, and its in vitro anti-cancer activity is significantly better than that of the classical metal anti-cancer drug cisplatin. Therefore, it has potential application value in the research and development of anti-cancer drugs for human lung cancer, human liver cancer, human breast cancer and human oral cancer. In summary, the anthraquinone dibutyltin complex of the present invention has good anti-cancer activity, low cost and simple preparation method, providing a new way for the development of new anti-cancer drugs. Brief Description of the Drawings

[0034] Figure 1 1H NMR spectrum of the organotin complex A1 prepared in Example 1 1 1H NMR spectrum.

[0035] Figure 2 13C NMR spectrum of the organotin complex A1 prepared in Example 1 13 13C NMR spectrum.

[0036] Figure 3 119Sn NMR spectrum of the organotin complex A1 prepared in Example 1 119 119Sn NMR spectrum.

[0037] Figure 4 HRMS spectrum of the organotin complex A1 prepared in Example 1

[0038] Figure 5 1H NMR spectrum of the organotin complex A2 prepared in Example 2 1 1H NMR spectrum.

[0039] Figure 6 13C NMR spectrum of the organotin complex A2 prepared in Example 2 13 13C NMR spectrum.

[0040] Figure 7 119Sn NMR spectrum of the organotin complex A2 prepared in Example 2 119 119Sn NMR spectrum.

[0041] Figure 8 HRMS spectrum of the organotin complex A2 prepared in Example 2

[0042] Figure 9 1H NMR spectrum of the organotin complex A3 prepared in Example 31 1H NMR spectrum

[0043] Figure 10 1H NMR spectrum of the organotin complex A3 prepared in Example 3 13 13C NMR spectrum

[0044] Figure 11 13C NMR spectrum of the organotin complex A3 prepared in Example 3 119 119Sn NMR spectrum

[0045] Figure 12 HRMS spectrum of the organotin complex A3 prepared in Example 3

[0046] Figure 13 1H NMR spectrum of the organotin complex A4 prepared in Example 4 1 1H NMR spectrum

[0047] Figure 14 1H NMR spectrum of the organotin complex A4 prepared in Example 4 13 13C NMR spectrum

[0048] Figure 15 13C NMR spectrum of the organotin complex A4 prepared in Example 4 119 119Sn NMR spectrum

[0049] Figure 16 HRMS spectrum of the organotin complex A4 prepared in Example 4

[0050] Figure 17 Crystal structure diagram of the organotin complex A2 prepared in Example 2

[0051] Figure 18 Crystal structure diagram of the organotin complex A4 prepared in Example 4 Detailed implementation mode

[0052] Example 1 Preparation of 9,10-anthraquinone-(3,5-dichlorosalicylaldehyde) Schiff base dibutyltin complex A1

[0053] Add 1 mmol of 2-amino-3-hydroxy-9,10-anthraquinone, 1 mmol of 3,5-dichlorosalicylaldehyde, 1 mmol of dibutyltin oxide and 30 mL of anhydrous methanol as solvent into a 50 mL round-bottom flask, heat under reflux for 8 h, cool, filter, and control the solvent evaporation and crystallization at room temperature to obtain brownish-red transparent crystals, which are 9,10-anthraquinone-(3,5-dichlorosalicylaldehyde) Schiff base dibutyltin complex A1. Yield: 88%.

[0054] Through nuclear magnetic resonance spectrum and high-resolution mass spectrometry structure analysis, the results are as follows:

[0055] 1 1H NMR (500 MHz, CDCl3) δ 8.92 - 8.74 (m, 1H), 8.27 (s, 1H), 8.23 (d, J = 7.1 Hz, 2H), 7.79 - 7.69 (m, 2H), 7.57 (s, 1H), 7.53 (d, J = 2.4 Hz, 1H), 7.27 (d, J = 2.4 Hz, 1H), 1.90 - 1.56 (m, 8H), 1.46 - 1.29 (m, 4H), 0.88 (t, J = 7.3 Hz, 6H).

[0056] 13 13C NMR (126 MHz, CDCl3) δ 182.82, 181.60, 164.99, 163.69, 163.50, 136.69, 136.14, 135.50, 133.94, 133.90, 133.78, 133.59, 132.52, 127.86, 127.10, 127.03, 123.21, 120.97, 118.29, 116.61, 115.11, 26.76, 26.60, 23.07, 13.56.

[0057] 119 119Sn NMR (187 MHz, CDCl3) δ -173.77.

[0058] HRMS (ESI) m / z calcd for C 29 H 27 Cl2NO4NaSn + [M + Na] + 666.0237, found 666.0228. Preparation of dibutyltin complex A2 of 9,10 - anthraquinone - (3,5 - dibromosalicylaldehyde) Schiff base

[0059] Add 1 mmol of 2 - amino - 3 - hydroxy - 9,10 - anthraquinone, 1 mmol of 3,5 - dibromosalicylaldehyde, 1 mmol of dibutyltin oxide and 30 mL of anhydrous methanol as the solvent into a 50 mL round - bottom flask. Heat under reflux for 8 h, cool, filter, and control the solvent evaporation for crystallization at room temperature to obtain a brown - red transparent crystal, which is the dibutyltin complex A2 of 9,10 - anthraquinone - (3,5 - dibromosalicylaldehyde) Schiff base. Yield: 82%.

[0060] The results of nuclear magnetic resonance spectroscopy, high - resolution mass spectrometry, and X - ray single - crystal diffraction structure analysis are as follows:

[0061] 11H NMR (500 MHz, CDCl3) δ 8.92 - 8.70 (m, 1H), 8.24 (dd, J = 13.6, 11.9 Hz, 3H), 7.81 (d, J = 2.3 Hz, 1H), 7.78 - 7.68 (m, 2H), 7.57 (s, 1H), 7.45 (d, J = 2.1 Hz, 1H), 1.86 - 1.55 (m, 8H), 1.45 - 1.31 (m, 4H), 0.89 (t, J = 7.3 Hz, 6H).

[0062] 13 13C NMR (126 MHz, CDCl3) δ 182.80, 181.59, 164.98, 164.40, 163.53, 142.14, 136.51, 136.07, 135.50, 133.95, 133.90, 133.78, 133.60, 127.11, 127.04, 123.22, 118.80, 118.38, 116.64, 115.12, 107.74, 26.74, 26.62, 23.10, 13.60.

[0063] 119 119Sn NMR (187 MHz, CDCl3) δ -173.45.

[0064] HRMS (ESI) m / z calcd for C 29 H 28 Br2NO4Sn + [M + H] + 731.9407, found 731.9403.

[0065] Crystallographic data: Monoclinic system, space group C2 / c, α = 90°, β = 99.516(2)°, γ = 90°, Z = 24, Dc = 1.743 Mg·m -3 , F(000) = 8640.0; The tin atom in the molecule has a five - coordinate trigonal bipyramidal configuration.

[0066] Example 3 Preparation of 9,10 - anthraquinone - (3,5 - di - tert - butylsalicylaldehyde) Schiff base dibutyltin complex A3

[0067] Add 1 mmol of 2-amino-3-hydroxy-9,10-anthraquinone, 1 mmol of 3,5-di-tert-butylsalicylaldehyde, 1 mmol of dibutyltin oxide and 30 mL of anhydrous methanol as the solvent into a 50 mL round-bottom flask. Heat under reflux for 8 h, cool, filter, and control the solvent to volatilize and crystallize at room temperature to obtain a brownish-red transparent crystal, which is the dibutyltin complex A4 of 9,10-anthraquinone-(3,5-di-tert-butylsalicylaldehyde) Schiff base. Yield: 86%.

[0068] The results of nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry structure analysis are as follows:

[0069] 1 H NMR(500MHz,CDCl3)δ9.06-8.83(m,1H),8.39-8.19(m,3H),7.83-7.69(m,2H),7.60(s,2H),7.15(d,J=2.0Hz,1H),1.76-1.51(m,8H),1.42(s,9H),1.36-1.31(m,12H),0.85(t,J=7.3Hz,6H).

[0070] 13 C NMR(126MHz,CDCl3)δ183.20,182.02,169.06,165.41,164.89,141.45,139.28,137.16,134.67,134.14,134.08,133.99,133.75,133.42,129.85,127.03,127.00,123.02,117.11,115.95,114.17,35.26,34.15,31.14,29.41,26.86,26.64,22.53,13.49.

[0071] 119 Sn NMR(187MHz,CDCl3)δ-176.24.

[0072] HRMS(ESI)m / z calcd for C 37 H 46 NO4Sn + [M+H] + 688.2449,found 688.2451.

[0073] Example 4 Preparation of dibutyltin complex A4 of 9,10-anthraquinone-(3-bromo-5-chlorosalicylaldehyde) Schiff base

[0074] Add 1 mmol of 2-amino-3-hydroxy-9,10-anthraquinone, 1 mmol of 3-bromo-5-chlorosalicylaldehyde, 1 mmol of dibutyltin oxide and 30 mL of anhydrous methanol as the solvent into a 50 mL round-bottom flask. Heat under reflux for 8 h, cool, filter, and control the evaporation of the solvent at room temperature to crystallize, obtaining a brownish-red transparent crystal, which is the dibutyltin complex A4 of 9,10-anthraquinone-(3-bromo-5-chlorosalicylaldehyde) Schiff base. Yield: 80%.

[0075] The results of nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and X-ray single crystal diffraction structure analysis are as follows:

[0076] 1 H NMR(500MHz,CDCl3)δ8.91-8.70(m,1H),8.33-8.14(m,3H),7.84-7.66(m,3H),7.56(s,1H),7.31(s,1H),1.92-1.55(m,8H),1.48-1.28(m,4H),0.89(t,J=7.3Hz,6H).

[0077] 13 C NMR(126MHz,CDCl3)δ182.78,181.57,164.97,164.07,163.62,139.74,136.08,135.48,133.92,133.88,133.76,133.58,133.34,127.09,127.02,123.20,121.47,118.09,117.93,116.61,115.13,26.75,26.62,23.07,13.60.

[0078] 119 Sn NMR(187MHz,CDCl3)δ-173.48.

[0079] HRMS(ESI)m / z calcd for C 29 H 28 ClBrNO4Sn + [M+H] + 687.9912,found 687.9905.

[0080] Crystallographic data: Triclinic system, space group P-1, α=62.2300(10)°,β=80.2890(10)°,γ=80.0470(10)°,Z=6, Dc=1.685Mg·m -3 , F(000) = 2052.0; The tin atom in the molecule has a trigonal bipyramidal configuration with five coordination sites.

[0081] Application Example: MTT assay for detecting the proliferation effect of compounds on tumor cells

[0082] Human lung cancer (A549), human liver cancer (HepG2), human breast cancer (MDA-MB-231), and human oral cancer (CAL-27) cells in the logarithmic growth phase were seeded into 96-well culture plates at a density of 3 - 5×10 3 cells / well. After the cells adhered for 24 h, the original culture medium was carefully discarded. In the negative control group, 100 μL of culture medium was added. In the experimental groups, 100 μL of compound solutions with different concentrations were added respectively. In the positive control groups, 100 μL of drug solutions with different concentrations were added respectively. Three parallel replicate wells were set for each concentration. The plates were then incubated in an incubator at 37 °C and 5% CO2 for another 48 h. Then, 20 μL of MTT solution at 5 mg·L -1 was added to each well and incubated for another 4 h. The supernatant was carefully discarded, and 100 μL of DMSO was added to each well to dissolve the formazan crystals. The plates were shaken at low speed for 10 min, and the absorbance values (OD values) of each well were measured at a wavelength of 490 nm using a fully automatic microplate reader. The inhibition rate of cell growth was calculated according to the following formula.

[0083] Cell growth inhibition rate % = [1 - (OD value of the drug-treated group / OD value of the blank group)] × 100%.

[0084] The results are shown in Table 1. The conclusion is: As can be seen from the data in the table, when the 9,10-anthraquinone-(3,5-disubstituted salicylaldehyde) Schiff base dibutyltin complex of the present invention is used as an anticancer drug, it has certain efficacy against human lung cancer (A549), human liver cancer (HepG2), human breast cancer (MDA-MB-231), and human oral cancer (CAL-27) cells. The anticancer activities of most complexes are superior to those of the positive control drug cisplatin. Therefore, it can be used as a candidate compound for anticancer drugs and has potential application value.

[0085] Table 1 Effects of different complexes on the in vitro proliferation of different cancer cells

[0086]

[0087]

Claims

1. A 9,10-anthraquinone-(3,5-disubstituted salicylaldehyde) Schiff base dibutyltin complex, characterized in that A compound of the following structural formula (I): wherein, R 1 or R 2 is -Cl, -Br, -C(CH3)3.

2. The anthraquinone dibutyltin complex according to claim 1, characterized in that: When R 1 and R 2 are both -Br, the complex is A2, and its crystal is monoclinic, space group C2 / c, α = 90°, β = 99.516(2)°, γ = 90°, Z = 24, Dc = 1.743 Mg·m -3 , F(000) = 8640.0; the tin atom in the molecule has a pentacoordinate trigonal bipyramidal configuration; When R 1 is -Br and R 2 is -Cl, the complex is A4, and its crystal is triclinic, space group P-1, α = 62.2300(10)°, β = 80.2890(10)°, γ = 80.0470(10)°, Z = 6, Dc = 1.685 Mg·m -3 , F(000) = 2052.0; the tin atom in the molecule has a pentacoordinated trigonal bipyramidal configuration.

3. Use of the anthraquinone dibutyltin complex according to claim 1 in the preparation of an anti-tumor drug.

4. The application according to claim 3, wherein: The tumor is lung cancer, liver cancer, breast cancer or oral cancer.

5. The application according to claim 4, wherein: The lung cancer, liver cancer, breast cancer, and oral cancer are respectively derived from human lung cancer cell line A549, human liver cancer cell line HepG2, human breast cancer cell line MDA-MB-231, and human oral cancer cell line CAL-27.

6. The preparation method of the anthraquinone dibutyltin complex according to claim 1, characterized in that: Using 2-amino-3-hydroxyanthraquinone, 3,5-disubstituted salicylaldehyde and dibutyltin oxide as raw materials, and anhydrous methanol as a solvent, the reaction is completed under the condition of heating under reflux.

7. The preparation method according to claim 6, wherein: The 3,5-disubstituted salicylaldehyde is 3,5-dichlorosalicylaldehyde, 3,5-dibromosalicylaldehyde, 3,5-di-tert-butylsalicylaldehyde, 3-bromo-5-chlorosalicylaldehyde.

8. The preparation method according to claim 6, characterized in that: The molar ratio of 2-amino-3-hydroxyanthraquinone, 3,5-disubstituted salicylaldehyde and dibutyltin oxide is 1:1:

1.

9. The preparation method according to claim 8, characterized in that: Add 1 mmol of 2-amino-3-hydroxyanthraquinone, 1 mmol of 3,5-disubstituted salicylaldehyde, 1 mmol of dibutyltin oxide and 30 ml of anhydrous methanol as a solvent into a flask, react for 8 h under the condition of heating under reflux, cool, filter, and control the solvent evaporation and crystallization at room temperature to obtain the product.

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