CN111138478B - Tricyclohexyltin quinoxaline-2-formate complex, and preparation method and application thereof - Google Patents
Tricyclohexyltin quinoxaline-2-formate complex, and preparation method and application thereof Download PDFInfo
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Abstract
The invention discloses a tricyclohexyltin quinoxaline-2-formate complex, a preparation method and application thereof, which are complexes of the following structural formula (I)
Description
Technical Field
The invention relates to a tricyclohexyltin quinoxaline-2-formate complex, a preparation method thereof and application of the complex in preparing antitumor drugs.
Background
Since Brown first discovered organotin carboxylates (CH 3 CO 2 SnPh 3 ) The synthesis, structure and biological activity research of the organotin carboxylate complex are widely focused by scientists since the biological activity of inhibiting the tumor of mice is inhibited. However, the known organotin compounds are generally highly toxic and therefore limited in application. Studies have shown that the structure, reactivity and biological activity of organotin compounds are related to both the hydrocarbon-based structure directly attached to the tin atom and the nature of the ligand. The organic tin complex structure is optimized through molecular design, so that the balance between toxicity and biological activity of the organic tin complex is regulated, and the organic tin complex is an important direction of current research. The coordination mode of tin atoms can be greatly changed by functionalizing hydrocarbon groups or ligands, so that the biological activity of the organotin complex is affected. Studies have shown that the toxicity of organotin compounds is related to their relative molecular masses, with smaller relative molecular masses being more toxic and larger relative molecular masses being more bulky hydrocarbyl tin. Therefore, the novel large steric hindrance alkyl tin complex is synthesized, and the structure and the biological activity of the complex are researched, so that the complex has important research significance.
It is well known that azacyclic rings are important and common structural units of medicines, pesticides, functional materials, etc., most of which are closely related to life systems, so that studying the structure of organotin derivatives of such ligands can provide useful information not only for the disclosed anticancer mechanism, but also for the development of novel drugs as possible molecular designs. It is necessary to synthesize a novel nitrogen-containing heterocyclic organotin carboxylate compound and conduct a study on the bioactivity of the compound, the nitrogen-containing heteroatom carboxylic acid being an important carboxylic acid ligand. For example, chinese patent CN101402650B discloses an application of a dibutyl tin and quinolinecarboxylic acid complex in preparing medicines for treating gastric cancer, nasopharyngeal carcinoma, human liver cancer or leukemia.
Based on the fact that the tricyclohexyl tin hydroxide is a substance with good biological activity, and the cyclohexyl has the characteristics of large steric hindrance, large molecular weight and the like, the tricyclohexyl tin hydroxide is selected to react with heterocyclic carboxylic acid ligand quinoxaline-2-formic acid under certain conditions, and a complex with strong inhibition activity on A549 (human lung cancer cells), hela (human cervical cancer cells) and HGC-27 (human gastric cancer cells) is synthesized, so that a new approach is provided for developing anticancer drugs.
Disclosure of Invention
In view of the above problems of the prior art, a first object of the present invention is to provide a tricyclohexyltin quinoxaline-2-carboxylate complex.
A second object of the present invention is to provide a process for producing the above tricyclohexylstannquinoxaline-2-carboxylate complex.
The third object of the invention is to provide an application of the tricyclohexyltin quinoxaline-2-formate complex in preparing anticancer drugs.
As a first aspect of the present invention, a tricyclohexylstannquinoxaline-2-carboxylic acid ester complex is a complex of the following structural formula (I):
(I)。
the tricyclohexyltin quinoxaline-2-formate complex of the present invention is subjected to element analysis, infrared spectrum analysis and nuclear magnetic resonance spectrum, and the results are as follows:
elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
The tricyclohexyltin quinoxaline-2-formate complex of the invention has the structural characteristics that: the central tin in the molecule forms a distorted tetrahedral configuration with the coordinating atoms.
As a preparation method of the tricyclohexyltin quinoxaline-2-formate complex, which is the second aspect of the invention, in a 250 mL round bottom flask, tricyclohexyltin hydroxide, quinoxaline-2-formic acid and solvent toluene are sequentially arranged, a Dean-Stark water separator is arranged, and heating reflux reaction is carried out for 6-12 hours at 112-120 ℃. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex.
In a preferred embodiment of the present invention, the mass ratio of the tricyclohexyltin hydroxide to the quinoxaline-2-carboxylic acid is 1 (1-1.1).
In a preferred embodiment of the invention, the solvent toluene is added in an amount of 25-35 ml per millimole of tricyclohexyl tin hydroxide.
The application of the tricyclohexyltin quinoxaline-2-formate complex as the third aspect of the invention in preparing anticancer drugs.
The applicant carries out in vitro anti-tumor activity confirmation research on the complex, and confirms that the complex has certain anti-tumor biological activity, namely the application of the complex in preparing anti-tumor drugs, in particular the application in preparing anti-human lung cancer drugs, human cervical cancer drugs and human gastric cancer drugs.
The tricyclohexyltin quinoxaline-2-formate complex disclosed by the invention has good anticancer activity on human lung cancer cells, human cervical cancer cells, human gastric cancer cells and the like, and can be used as a raw material for preparing medicines for resisting lung cancer, cervical cancer and gastric cancer. Compared with the currently commonly used platinum anti-cancer drugs, the tricyclohexyltin quinoxaline-2-formate complex has the characteristics of high anti-cancer activity, low cost, simple preparation method and the like, and provides a new way for developing anti-cancer drugs.
Drawings
FIG. 1 is an IR spectrum of tricyclohexyltin quinoxaline-2-carboxylate complex.
FIG. 2 is a tricyclohexyltin quinoxaline-2-carboxylate complex 1 H NMR spectrum.
FIG. 3 is a tricyclohexyltin quinoxaline-2-carboxylate complex 13 C NMR spectrum.
FIG. 4 is a tricyclohexyltin quinoxaline-2-carboxylate complex 119 Sn NMR spectrum.
Detailed Description
The present invention is further illustrated in detail by the following examples, but it should be noted that the scope of the present invention is not limited by any of these examples.
Example 1:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 0.3851g (1 mmol) of tricyclohexyltin hydroxide, 0.1743 g (1 mmol) of quinoxaline-2-carboxylic acid, 25 mmol of toluene as solvent and mL were successively added, and the mixture was put on a Dean-Stark trap and heated to reflux at 112-120℃for reaction 6 h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 82%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Example 2:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
to a 250 mL round bottom flask were added 3853g (1.0 mmol) of tricyclohexyltin hydroxide, 0.1915g (1.1 mmol) of quinoxaline-2-carboxylic acid, 25 g (mL) of toluene as a solvent, and the mixture was charged with a Dean-Stark trap and heated to reflux at 112-120℃for reaction 8 h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 80%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Example 3:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 0.3851g (1.0 mmol) of tricyclohexyltin hydroxide, 0.1916g (1.1 mmol) of quinoxaline-2-carboxylic acid, 35 mL of toluene as solvent and a Dean-Stark trap were added in this order, and the reaction was performed under reflux at 112-120℃with heating 8 h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 82%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18.Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Example 4:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 0.7709g (2.0 mmol) of tricyclohexyltin hydroxide, 0.3654g (2.1 mmol) of quinoxaline-2-carboxylic acid, 50 mL of toluene as solvent and a Dean-Stark trap were added in this order, and the reaction was performed under reflux at 112-120℃with heating 8 h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 83%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Example 5:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 0.7701g (2.0 mmol) of tricyclohexyltin hydroxide, 0.3485g (2.0 mmol) of quinoxaline-2-carboxylic acid, 60. 60 mL of toluene as solvent and a Dean-Stark trap were added in this order, and the reaction was performed under reflux at 112-120℃with heating 12h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 82%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Example 6:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 1.1551g (3.0 mmol) of tricyclohexyltin hydroxide, 0.5224g (3.0 mmol) of quinoxaline-2-carboxylic acid, 75. 75 mL of toluene as solvent and a Dean-Stark trap were added in this order, and the reaction was performed under reflux at 112-120℃with heating 12h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 84%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15, 28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Example 7:
preparation of tricyclohexyltin quinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, tin 1.1553 g (3.0 mmol), quinoxaline-2-carboxylic acid 0.5748g (3.3 mmol), toluene 90 mL as solvent, and a Dean-Stark trap were added in this order, and the reaction was performed under reflux at 112-120℃with heating of 6 h. After the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex. Yield: 82%, melting point: 130-133 ℃.
Elemental analysis (C) 27 H 38 N 2 O 2 Sn): theoretical value: c,59.91; h,7.08; n,5.18. Measurement value: c,59.93; h,7.02; n,5.23.
IR(KBr, v/cm -1 ): 3730.33(m), 2918.30(s), 2845.00(m), 2650.19(w), 1633.71(s), 1490.97(m), 1444.68(m), 1365.60(s), 1325.10(m), 1247.94(w), 1203.58(w), 1168.86(m), 1126.43(w), 1085.92(w), 1020.34(m), 993.34(m), 956.69(w), 802.39(m), 754.17(s), 680.87(m), 653.87(m), 599.86(m), 522.71(w), 491.85(w),418.55(m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.55(s, 1H), 8.32 (d,J =8Hz, 1H), 8.15 (d,J =8Hz, 1H), 7.86-7.80 (m, 2H), 2.12-1.96 (m, 9H), 1.81-1.64 (m, 15H), 1.43-1.35(m, 9H)。
13 C NMR(CDCl 3 , 125 MHz), δ(ppm): 168.01, 146.05, 144.88, 143.26, 141.92, 131.50, 130.81, 130.40, 129.11, 34.56, 31.15,28.93(t, J = 32 Hz), 26.84。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 38.38。
Test example:
the tricyclohexyltin quinoxaline-2-formate complex of the invention has in vitro anticancer activity determination realized by MTT experimental method.
MTT assay:
based on the metabolic reduction of 3- (4, 5-dimethylazol-2-yl) -2,5-diArenyltetrazolium bromide. Succinate dehydrogenase in the mitochondria of living cells reduces exogenous MTT to water insoluble blue-violet crystalline Formazan (Formazan) and deposits in cells, whereas dead cells do not. Dimethyl sulfoxide (DMSO) can dissolve formazan in cells, and the optical density of characteristic wavelength can be measured by an enzyme-labeled instrument, so that the number of living cells can be indirectly reflected.
The inhibitory activity of the tricyclohexyltin quinoxaline-2-carboxylate complex prepared in example 1 on human lung cancer cells (A549), human cervical cancer cells (Hela), and human gastric cancer cells (HGC-27) was measured by the MTT method.
Cell lines and culture system: a549, hela, and HGC-27 cell lines were obtained from American Tissue Culture Collection (ATCC). With 10% fetal bovine serum in RPMI1640 (GIBICO) medium at 5% (volume fraction) CO 2 In vitro culture was performed in a saturated humidity incubator at 37 ℃.
The testing process comprises the following steps: the test liquid medicine (0.0625 mu mol/L-0.5 mu mol/L) is added into each hole according to concentration gradient, and 3 parallel holes are arranged for each concentration. The experiments were divided into drug test groups (with different concentrations of test agent added), control groups (with only culture fluid and cells without test agent) and blank groups (with only culture fluid and no cells and test agent). The orifice plate after the drug addition is placed at 37 ℃ and 5 percent CO 2 Culturing in an incubator for 24 hours. The activity of the control drug was determined by the method of the test sample. In the well plate after 48 hours of incubation, MTT 20uL (5 g/L in PBS) was added to each well. After 4h at 37℃the supernatant was removed. 150uL DMSO was added to each well and the mixture was shaken for 10min to dissolve Formazan crystals. Finally, absorbance values of each well were measured at 570nm using a BioTek multifunctional microplate reader.
And (3) data processing: data processing using the GraAr Pad Prism version5.0 program, complex IC 50 Fitting is performed through a nonlinear regression model with S-shaped dose response in the program.
Human lung cancer cell (A549) cell strain, human cervical cancer cell (Hela) cell strain and human gastric cancer cell (HGC-2) by MTT assay7) Cell lines were analyzed and their IC was measured 50 Values, results are shown in table 1, conclusions are: as shown in the table, the tricyclohexyltin quinoxaline-2-formate complex of the invention is used as an anticancer drug, has high anticancer activity on human lung cancer, human cervical cancer and human gastric cancer, and can be used as a candidate complex of the anticancer drug.
Table 1 tricyclohexyltin quinoxaline-2-carboxylate complex anticancer drug in vitro activity test data.
| Human lung cancer cell | Human cervical cancer cell | Human gastric cancer cell | |
| Cell strain | A549 | Hela | HGC-27 |
| IC 50 μM | 0.2314 | 0.1463 | 0.2467 |
The test methods of the anti-cancer activity of the tricyclohexyltin quinoxaline-2-formate complex prepared in the other examples on human lung cancer cells (A549), human cervical cancer cells (Hela) and human gastric cancer cells (HGC-27) by the MTT method are the same as those of the test examples, and the test results are basically the same as those of Table 1.
Claims (4)
1. A tricyclohexyltin quinoxaline-2-formate complex is a complex of the following structural formula (I):
2. the preparation method of the tricyclohexyltin quinoxaline-2-formate complex according to claim 1, which is characterized in that tricyclohexyltin hydroxide, quinoxaline-2-formic acid and solvent toluene are sequentially added into a 250 mL round bottom flask, a Dean-Stark water separator is arranged, and heating reflux reaction is carried out for 6-12 hours at 112-120 ℃; after the reaction is finished, filtering while the solution is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain a white solid, and recrystallizing the white solid by using ethanol to obtain the tricyclohexyltin quinoxaline-2-formate complex;
the mass ratio of the tricyclohexyl tin hydroxide to the quinoxaline-2-formic acid is 1 (1-1.1).
3. The preparation method according to claim 2, wherein the toluene solvent is added in an amount of 25-35 ml per millimole of tricyclohexyl tin hydroxide.
4. The use of the tricyclohexyltin quinoxaline-2-formate complex according to claim 1 for preparing anticancer drugs, wherein the cancer cells are lung cancer, cervical cancer and gastric cancer.
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