Tin-oxygen-heterocycle-structured dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate complex as well as preparation method and application thereof

A technology of dibutyltin and benzoate, applied in tin organic compounds, compounds of group 4/14 elements of the periodic table, organic chemical methods, etc., can solve the problems of no anticancer activity and high or low anticancer activity, and achieve Good anticancer activity, high anticancer activity, low cost effect

Inactive Publication Date: 2017-01-04
HENGYANG NORMAL UNIV
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  • Abstract
  • Description
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Problems solved by technology

Existing studies have shown that the hydrocarbon group R in organotin is the main factor determining the anticancer activity of the compound. For example, cyclohexyl, n-butyl and phenyltin compounds have strong anticancer activity, followed by ethyl, and methyl almost no anticancer activity

Method used

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  • Tin-oxygen-heterocycle-structured dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate complex as well as preparation method and application thereof
  • Tin-oxygen-heterocycle-structured dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate complex as well as preparation method and application thereof
  • Tin-oxygen-heterocycle-structured dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate of tin-oxygen heterocyclic structure:

[0034] Add 0.2062g (1mmol) of 2,4,5-trifluoro-3-methoxy-benzoic acid, 0.2493g (1mmol) of dibutyltin oxide, and 20mL of solvent ethanol in sequence in a 100ml round-bottomed flask. React at 50~65°C for 8 hours; cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain light yellow transparent crystals, which are dibutyltin 2,4,5-trifluoro-3-methanol Oxy-benzoate complexes. Yield: 78%, melting point: 124-125°C.

[0035] Elemental analysis (C 128 h 176 o 28 f 24 sn 8 ): theoretical value: C, 43.08; H, 4.97. Found: C, 43.11; H, 4.95.

[0036] IR(KBr, cm -1 ): 3078, 2957, 2930, 2872 v(C-H), 1583 v as (COO - ), 1396v as (COO - ), 635 v(Sn-C), 474 v(Sn-O).

[0037] 1H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.45(d, 8H, Ar-H), 4.08(s, 24H, -O-CH 3 ), 0.78-1.73 (m, 144H, Bu-H).

[0038] 119 Sn NMR (CDCl 3 , 186 MHz), δ(ppm): -212.41, -2...

Embodiment 2

[0041] Preparation of dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate of tin-oxygen heterocyclic structure:

[0042] Add 0.2062g (1mmol) of 2,4,5-trifluoro-3-methoxy-benzoic acid, 0.2490g (1.05mmol) of dibutyltin oxide, and 20mL of solvent ethanol in sequence in a 100ml round bottom flask. React at a temperature of 50~65°C for 8 hours; cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain light yellow transparent crystals, which are dibutyltin 2,4,5-trifluoro-3- Methoxy-benzoate complex. Yield: 79%, melting point: 124-125°C.

[0043] Elemental analysis (C 128 h 176 o 28 f 24 sn 8 ): theoretical value: C, 43.08; H, 4.97. Found: C, 43.11; H, 4.95.

[0044] IR(KBr, cm -1 ): 3078, 2957, 2930, 2872 v(C-H), 1583 v as (COO - ), 1396v as (COO - ), 635 v(Sn-C), 474 v(Sn-O).

[0045] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.45(d, 8H, Ar-H), 4.08(s, 24H, -O-CH 3 ), 0.78-1.73 (m, 144H, Bu-H).

[0046] 119 Sn NMR (CDCl 3 , 186 MHz), δ(ppm)...

Embodiment 3

[0049] Preparation of dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate of tin-oxygen heterocyclic structure:

[0050] Add 0.4123g (2mmol) of 2,4,5-trifluoro-3-methoxy-benzoic acid, 0.5220g (2.10mmol) of dibutyltin oxide, and 55mL of solvent ethanol in sequence in a 100ml round bottom flask. React at a temperature of 50~65°C for 18 hours; cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain light yellow transparent crystals, which are dibutyltin 2,4,5-trifluoro-3- Methoxy-benzoate complex. Yield: 80%, melting point: 124-125°C.

[0051] Elemental analysis (C 128 h 176 o 28 f 24 sn 8 ): theoretical value: C, 43.08; H, 4.97. Found: C, 43.11; H, 4.95.

[0052] IR(KBr, cm -1 ): 3078, 2957, 2930, 2872 v(C-H), 1583 v as (COO - ), 1396v as (COO - ), 635 v(Sn-C), 474 v(Sn-O).

[0053] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 7.45(d, 8H, Ar-H), 4.08(s, 24H, -O-CH 3 ), 0.78-1.73 (m, 144H, Bu-H).

[0054] 119 Sn NMR (CDCl 3 , 186 MHz), δ(ppm...

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Abstract

The invention discloses tin-oxygen-heterocycle-structured dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate, which is a complex having the structural formula (I) (shown in the description), wherein R represents n-butyl. The invention further discloses a preparation method of the complex and application of the complex in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a dibutyltin 2,4,5-trifluoro-3-methoxy-benzoate complex, a preparation method thereof, and the complex dibutyltin 2,4,5-trifluoro-3 -Application of methoxyl-benzoate in the preparation of antineoplastic drugs. Background technique [0002] Organotin is a class of metal-organic compounds containing Sn-C bonds, which has high biological activity and has broad application prospects in the fields of sterilization, insecticide, and anticancer drug preparation. Existing studies have shown that the hydrocarbon group R in organotin is the main factor determining the anticancer activity of the compound. For example, the anticancer activity of cyclohexyl, n-butyl and phenyltin compounds is stronger, followed by ethyl, and methyl almost no anticancer activity. The structure of the ligand also plays an important role in the anticancer activity of the complex and the broad spectrum of killing cancer cells. Experiments have proved that the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61K31/555A61P35/00
CPCC07F7/2296C07B2200/13
Inventor 朱小明庾江喜蒋伍玖张复兴冯泳兰邝代治李俊华谭宇星
Owner HENGYANG NORMAL UNIV
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