CN111138475B - Tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex and preparation method and application thereof - Google Patents
Tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex and preparation method and application thereof Download PDFInfo
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- VIKWPCOTVURCSL-UHFFFAOYSA-M tris(2-methyl-2-phenylpropyl)stannyl 3-methyl-1-benzofuran-2-carboxylate Chemical compound CC1=C(OC2=C1C=CC=C2)C(=O)[O-].CC(C[Sn+](CC(C)(C)C2=CC=CC=C2)CC(C)(C)C2=CC=CC=C2)(C)C2=CC=CC=C2 VIKWPCOTVURCSL-UHFFFAOYSA-M 0.000 description 1
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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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Abstract
The invention discloses a tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex and a preparation method and application thereof, which are complexes of the following structural formula (I):
. The invention also discloses a preparation method of the tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex and application thereof in preparing antitumor drugs.
Description
Technical Field
The invention relates to a tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex, a preparation method thereof and application of the complex in preparing antitumor drugs.
Background
Since Brown discovered for the first time that organotin carboxylates (CH 3CO2SnPh 3) have inhibitory activity against mouse tumor bioactivity, studies on the synthesis, structure and bioactivity of organotin carboxylate complexes have received extensive attention from scientists. 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 bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide is a substance with good biological activity, and the 2-methyl-2-phenylpropyl has the characteristics of large steric hindrance, large molecular weight and the like, bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide is selected to react with heterocyclic carboxylic acid ligand 3-methylbenzofurancarboxylic 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex
It is a second object of the present invention to provide a process for the preparation of the above tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex.
The third object of the invention is to provide the application of the tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex in preparing anticancer drugs.
As a first aspect of the present invention, a tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran carboxylate complex is a complex of the following structural formula (I):
(I)。
the three (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex is subjected to elemental analysis, infrared spectrum analysis, nuclear magnetic resonance spectrum and X-ray single crystal structure analysis, and the results are as follows:
elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex of the present invention is a crystalline structure, and the crystallographic data thereof are that: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
the tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex of the invention is structurally characterized in that: the central tin in the molecule forms a distorted tetrahedral configuration with the coordinating atoms.
As a preparation method of the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex in the second aspect of the invention, bis [ tris (2-methyl-2-phenylpropyl) ] tin, 3-methylbenzofuran formic acid and toluene serving as a solvent are sequentially oxidized in a 250 mL round-bottomed 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 mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex.
In a preferred embodiment of the present invention, the ratio of the amounts of the substances of the bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide and the 3-methylbenzofuran carboxylic acid is 1.0 (2.0 to 2.2).
In a preferred embodiment of the invention, the solvent toluene is added in an amount of 25 to 35 ml per millimole of tin bis [ tris (2-methyl-2-phenylpropyl) ] oxide.
The invention relates to an application of a tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formic acid complex of 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 medicaments for resisting lung cancer, cervical cancer and gastric cancer. Compared with the currently commonly used platinum anti-cancer drugs, the tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran 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 a diagram showing the structure of the crystal molecular structure of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex.
FIG. 2 is an IR spectrum of a tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex.
FIG. 3 is a tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex 1 H NMR spectrum.
FIG. 4 is a tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex 13 C NMR spectrum.
FIG. 5 is a tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex:
in a 250 mL round bottom flask, 1.0531g (1.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.3528 g (2.0 mmol) of 3-methylbenzofuran carboxylic acid, and 25. 25 mL of toluene were added sequentially, and the mixture was put in a Dean-Stark trap and heated to reflux at 112-120℃for reaction 6 h. After the reaction is finished, filtering while the mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
example 2:
preparation of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex:
in a 250 mL round bottom flask, 1.0540g (1.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.3880 g (2.2 mmol) of 3-methylbenzofuran carboxylic acid, and 25. 25 mL of toluene were added sequentially, and the mixture was put in a Dean-Stark trap and heated to reflux at 112-120℃for reaction 8 h. After the reaction is finished, filtering while the mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
example 3:
preparation of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex:
in a 250 mL round bottom flask, bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide 1.0534 g (1.0 mmol), 3-methylbenzofuran carboxylic acid 0.3885 g (2.2 mmol), solvent toluene 35 mL, and a Dean-Stark trap were added sequentially, and the mixture was heated to reflux at 112-120℃for reaction 8 h. After the reaction is finished, filtering while the mixture is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain yellow solid, and recrystallizing the yellow solid by using ethanol to obtain the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
example 4:
preparation of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex:
in a 250 mL round bottom flask, bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide 2.1068 g (2.0 mmol), 3-methylbenzofuran carboxylic acid 0.7405 g (4.2 mmol), solvent toluene 50 mL, and a Dean-Stark trap were added sequentially, and the mixture was heated to reflux at 112-120℃for reaction 8 h. After the reaction is finished, filtering while the mixture is hot, removing the solvent from the filtrate by using a rotary evaporator to obtain yellow solid, and recrystallizing the yellow solid by using ethanol to obtain the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
example 5:
preparation of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate:
in a 250 mL round bottom flask, bis [ tris (2-methyl-2-phenylpropyl) ] tin 2.1060 g (2.0 mmol), 3-methylbenzofuran carboxylic acid 0.7048 g (4.0 mmol) and solvent toluene 60 mL were added sequentially, and the mixture was fitted with a Dean-Stark trap and heated to reflux at 112-120℃for reaction 12 h. After the reaction is finished, filtering while the mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
example 6:
preparation of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate:
in a 250 mL round bottom flask, 3.1595g (6.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 1.060 g (6.0 mmol) of 3-methylbenzofuran carboxylic acid, 75 mL of toluene solvent, and a Dean-Stark trap were added in this order, and the mixture was heated to reflux at 112-120℃for reaction 12 h. After the reaction is finished, filtering while the mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
example 7:
preparation of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate:
in a 250 mL round bottom flask, 3.1595g (3.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 1.1632 g (6.6 mmol) of 3-methylbenzofuran carboxylic acid, 90 mL of toluene as solvent, and a Dean-Stark trap were added in this order, and the mixture was heated to reflux at 112-120℃for reaction 6 h. After the reaction is finished, filtering while the mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate. Yield: 70%, melting point: 112-114 ℃.
Elemental analysis (C) 40 H 46 O 3 Sn): theoretical value: c,69.28; h,6.69. Measurement value: c,69.32; h,6.65.
IR (KBr, v/cm -1 ): 3722.26 (m), 3628.10 (m), 3055.24 (m), 2962.66 (m), 2922.16 (m), 2860.43 (m), 1656.85 (s), 1492.90 (m), 1440.83 (m), 1386.82 (s), 1305.81 (s), 1273.02 (ｍ), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w), 767.67 (s), 742.59 (m), 700.16 (s), 653.87 (m), 619.15 (w), 547.78 (m), 488.06 (w)。
1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.61 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.5Hz, 1H), 7.40 (t, J =7.5Hz, 1H), 7.30-7.27 (m, 7H), 7.20 (t, J=7, 3H), 7.10 (d, J=8Hz, 6H), 2.54 (s, 3H), 1.30 (s, 6H), 1.24 (s, 18H)。
13 C NMR (CDCl 3 , 125 MHz), δ(ppm): 1164.45, 154.18, 150.81, 143.30, 129.58, 128.34, 126.80, 125.83, 125.27, 122.61, 120.79, 112.08, 37.70, 32.84 (t, J=22.5 Hz), 9.59。
119 Sn NMR (CDCl 3 , 186 MHz), δ (ppm): 102.13。
The crystallographic data thereof: the crystals belong to monoclinic system and space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16) nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 ，Dc=1.289 Mg·m -3 ，μ(MoKa)= 0.750 mm -1 ，F(000)= 1440，2.22°＜θ< 27.65 °, crystal size: 0.21 x 0.19 x 0.23 mm,R=0.0469，wR=0.0907。
test example:
the in vitro anticancer activity of the tri (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate is measured by an MTT (methyl thiazolyl tetrazolium) 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate prepared in example 1 on human lung cancer cells (A549), human cervical cancer cells (Hela), and human gastric cancer cells (HGC-27) was determined by MTT assay.
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.
The IC of the human lung cancer cell (A549) cell strain, the human cervical cancer cell (Hela) cell strain and the human gastric cancer cell (HGC-27) cell strain are determined by an MTT assay 50 Values, results are shown in table 1, conclusions are: as can be seen from the data in the table, the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzene of the present inventionFuranate has high anticancer activity on human lung cancer, cervical cancer and gastric cancer, and can be used as candidate complex of anticancer drug.
Table 1 data for in vitro activity test of tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate anticancer drugs.
| Human lung cancer cell | Human cervical cancer cell | Human gastric cancer cell | |
| Cell strain | A549 | Hela | HGC-27 |
| IC 50 μM | 0.5084 | 0.4908 | 0.5323 |
The test method of the anti-cancer activity of the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate prepared in the rest examples on human lung cancer cells (A549), human cervical cancer cells (Hela) and human gastric cancer cells (HGC-27) by using an MTT method is the same as that of the test examples, and the test results are basically the same as those of Table 1.
Claims (4)
1. Tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex, being a complex of the following structural formula (I):
(I)；
the complex has a crystal structure, and the crystallographic data of the complex are as follows: monoclinic system, space groupP 2 1 /c，a=1.1696(2) nm，b=3.1954(5) nm，c=0.95629(16)nm，α=90°，β=91°，γ=90°，Z=4，V=3.5734(10) nm 3 The method comprises the steps of carrying out a first treatment on the surface of the The central tin in the molecule and the coordinating atoms form a distorted tetrahedral configuration.
2. The preparation method of the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex according to claim 1, which is characterized in that bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 3-methylbenzofuran formic acid and toluene solvent are sequentially added into a 250 mL round-bottomed 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 mixture 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 tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex;
the mass ratio of the two substances of the bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide and the 3-methylbenzofuran formic acid is 1.0 (2.0-2.2).
3. The preparation method according to claim 2, wherein the toluene solvent is added in an amount of 25-35 ml per millimole of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide.
4. The use of the tris (2-methyl-2-phenylpropyl) tin 3-methylbenzofuran formate complex according to claim 1 for the preparation of anticancer drugs, wherein the cancer cells aimed at are lung cancer, cervical cancer and gastric cancer.
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