CN111116637B - Tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex and preparation method and application thereof - Google Patents
Tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex and preparation method and application thereof Download PDFInfo
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- SGRZMLFKTFSWNM-UHFFFAOYSA-M tris(2-methyl-2-phenylpropyl)stannyl quinoxaline-2-carboxylate Chemical compound N1=C(C=NC2=CC=CC=C12)C(=O)[O-].CC(C[Sn+](CC(C)(C)C1=CC=CC=C1)CC(C)(C)C1=CC=CC=C1)(C)C1=CC=CC=C1 SGRZMLFKTFSWNM-UHFFFAOYSA-M 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- 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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Abstract
The invention discloses a tri (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex, a preparation method and application thereof, which is a complex with the following structural formula (I)
. The invention also discloses a preparation method of the tri (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex and application thereof in preparing antitumor drugs.
Description
Technical Field
The invention relates to a tri (2-methyl-2-phenylpropyl) stannquinoxaline-2-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 characteristics that the bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide is a substance with better biological activity, and the 2-methyl-2-phenylpropyl has larger steric hindrance, larger molecular weight and the like, the bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide is selected to react with the heterocyclic carboxylic acid ligand quinoxaline-2-formic acid under certain conditions, and the complex with stronger 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) stannquinoxaline-2-carboxylate complex.
A second object of the present invention is to provide a process for producing the above tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex.
The third object of the invention is to provide the application of the tri (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex in preparing anticancer drugs.
As a first aspect of the present invention, a tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex is a complex of the following structural formula (I):
(I)。
the three (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex provided by the invention is subjected to element analysis, infrared spectrum analysis, nuclear magnetic resonance spectrum and X-ray single crystal structure analysis, and the results are as follows:
elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293Mg·m -3 ，μ(MoKa)=0.753mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
the tri (2-methyl-2-phenylpropyl) stannquinoxaline-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 tris (2-methyl-2-phenylpropyl) tin quinoxaline-2-formate complex, according to the second aspect of the invention, bis [ tris (2-methyl-2-phenylpropyl) ] tin, quinoxaline-2-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 a heating reflux reaction is carried out at 112-120 ℃ for 6-12 hours. 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex.
In a preferred embodiment of the present invention, the mass ratio of the two substances of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide and quinoxaline-2-carboxylic acid is 1.0 (2.0-2.2).
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 use of a tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex as a third aspect of the present invention in the preparation of an anticancer drug.
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) stannquinoxaline-2-formate complex provided 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 anti-lung cancer, anti-cervical cancer and anti-gastric cancer drugs. Compared with the currently commonly used platinum anti-cancer drugs, the tris (2-methyl-2-phenylpropyl) stannquinoxaline-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 a diagram showing the structure of the crystal molecular structure of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex.
FIG. 2 is an IR spectrum of a tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex.
FIG. 3 is a diagram of a tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex 1 H NMR spectrum.
FIG. 4 is a diagram of a tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex 13 C NMR spectrum.
FIG. 5 is a diagram of a tris (2-methyl-2-phenylpropyl) stannquinoxaline-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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 1.0535g (1.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.3486g (2.0 mmol) of quinoxaline-2-carboxylic acid, and 25 mL of toluene as a solvent were sequentially added, and the mixture was charged with 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 77%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; the gas phase is taken as H,6.45；N，4.01。
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
the tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
example 2:
preparation of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 1.0534g (1.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.3832g (2.2 mmol) of quinoxaline-2-carboxylic acid, and 25 mL of toluene as a solvent were sequentially added, and the mixture was charged with a Dean-Stark trap and heated at 112-120℃to reflux 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 76%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
example 3:
preparation of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 1.0538g (1.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.3835g (2.2 mmol) of quinoxaline-2-carboxylic acid, 35 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℃to give 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 78%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The inventionThe clear tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex is in a crystal structure, and the crystallographic data of the complex are that: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
example 4:
preparation of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 2.1074g (2.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.7310g (4.2 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 of 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 78%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
example 5:
preparation of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 2.1078g (2.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 0.6975g (4.0 mmol) of quinoxaline-2-carboxylic acid, 60 mL solvent toluene, and a Dean-Stark trap were added sequentially, and the mixture was heated to reflux at 112-120℃for reaction 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 79%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
example 6:
preparation of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 3.1608g (3.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 1.0460g (6.0 mmol) of quinoxaline-2-carboxylic acid, 75 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 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 77%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR=0.1722。
example 7:
preparation of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex:
in a 250 mL round bottom flask, 3.1607g (3.0 mmol) of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 1.1506g (6.6 mmol) of quinoxaline-2-carboxylic acid, 90 mL of solvent toluene, and a Dean-Stark trap were added in this order, and the mixture was heated to reflux at 112-120℃to react 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex. Yield: 78%, melting point: 121-123 ℃.
Elemental analysis (C) 39 H 44 N 2 O 2 Sn): theoretical value: c,67.74; h,6.41; n,4.05. Measurement value: c,67.76; h,6.45; n,4.01.
IR(KBr, v/cm -1 ): 3728.40 (m), 3612.67 (m), 3055.24 (m), 2960.73 (m), 2920.23 (m), 2897.08 (m), 1680.00 (s), 1649.14 (w), 1492.90 (m), 1440.83 (m), 1384.89 (w), 1342.46 (m), 1309.97 (s), 1244.09 (m), 1190.08 (w),1165.00 (m), 1107.14 (m), 1074.35 (m), 1029.99 (w), 800.46 (m), 767.67 (s), 748.38 (m), 723.31 (m), 700.16 (s), 605.65 (m), 555.50 (m), 449.41 (m)。
1 H NMR(CDCl 3 , 500 MHz), δ(ppm):9.36 (s, 1H), 8.34 (d, J =8Hz, 1H), 8.17 (d, J =8Hz, 1H), 7.88-7.82 (m, 2H), 7.291 (t, J =7.5Hz, 6H), 7.20 (t, J=7Hz, 3H), 7.14 (d, J =7.5Hz, 6H), 1.35 (s,6H), 1.27 (s,18H)。
13 C NMR (CDCl 3 , 125MHz) δ(ppm): 167.13, 150.65, 145.81, 145.12, 143.17, 141.96, 131.46, 130.81, 130.41, 129.07, 128.42, 125.96, 125.27, 37.76, 32.84 (t, J = 22.8 Hz)。
119 Sn NMR(CDCl 3 , 186 MHz), δ(ppm): 112.64。
The tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex of the present invention has a crystal structure, and the crystallographic data thereof are as follows: the crystals belong to triclinic system, space group triclinic system and space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)nm 3 ，Dc=1.293 Mg·m -3 ，μ(MoKa)=0.753 mm -1 ，F(000)=716，2.25°＜θCrystal size < 25.01 °:0.25 x 0.0.22 x 0.19 x mm,R=0.0816，wR= 0.1722. Test example:
the tri (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex is realized by an MTT experimental method in vitro anticancer activity determination.
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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-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 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 (in PBS solution was added to each wellFormulated at 5 g/L). 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) stannquinoxaline-2-formate complex provided by 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 data for in vitro activity test of tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex anticancer drugs.
| Human lung cancer cell | Human cervical cancer cell | Human gastric cancer cell | |
| Cell strain | A549 | Hela | HGC-27 |
| IC 50 μM | 0.5246 | 0.4859 | 0.3558 |
The test methods of the anti-cancer activity of the tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex 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 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 tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-carboxylate complex, which is a complex of the following structural formula (I):
the tris (2-methyl-2-phenylpropyl) stannquinoxaline-2-formate complex is of a crystal structure, and the crystallographic data are as follows: triclinic system, space groupP-1，a=0.9762(4)nm，b=1.1553(3)nm，c=1.6907(7)nm，α=108°，β=101°，γ=91°，Z=2，V=1.7760(13)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) stannquinoxaline-2-formate complex according to claim 1, which is characterized in that bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, quinoxaline-2-formic acid and toluene solvent are sequentially added into a 250 mL round-bottomed flask, a Dean-Stark water separator is arranged, and the mixture is heated and refluxed 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) stannquinoxaline-2-formate complex;
the mass ratio of the two substances of the bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide and the quinoxaline-2-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) stannquinoxaline-2-carboxylate complex according to claim 1 for preparing an anticancer drug, wherein the cancer cells are lung cancer, cervical cancer and gastric cancer.
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