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Bi(tributyltin) trans-butene dibasic acid ester complex as well as preparation method and application thereof

A technology of fumaric acid ester and bis-tributyltin oxide, which can be used in tin organic compounds, drug combinations, anti-tumor drugs, etc., can solve the problems of no anti-cancer activity and high anti-cancer activity, and achieve good anti-cancer The effect of high activity, anticancer activity and low cost

Active Publication Date: 2017-01-04
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Bi(tributyltin) trans-butene dibasic acid ester complex as well as preparation method and application thereof
  • Bi(tributyltin) trans-butene dibasic acid ester complex as well as preparation method and application thereof
  • Bi(tributyltin) trans-butene dibasic acid ester complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of two (tributyltin) fumarate complexes:

[0034] Add 0.1181g (1mmol) of fumaric acid, 5968g (1mmol) of bis-tributyltin oxide) and 20mL of solvent methanol in sequence in a 100ml round bottom flask, and react for 8h at a temperature of 50~65°C; cool , filtered, and under the condition of 20~35°C, control the solvent volatilization and crystallization to obtain a white solid, which is bis(tributyltin)fumarate complex. Yield: 65%, melting point: 125-126°C.

[0035] Elemental analysis (C 28 h 56 o 4 sn 2 ): theoretical value: C, 48.45; H, 8.13. Found: C, 48.40; H, 8.16.

[0036] IR(KBr, cm -1 ): 2957, 2922, 2872, 2857v(C-H), 1570v as (COO - ), 1377v s (COO - ), 613v(Sn-C), 511v(Sn-O).

[0037] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 6.79(s, 2H, -CH=CH-), 0.90-1.65(m, 54H, Bu-H).

[0038] 13 C NMR (CDCl 3 , 125 MHz), δ (ppm): 170.58 (COO), 134.71 (-CH=CH-), 27.77, 27.03, 16.56, 13.66 (Bu).

[0039] 119 Sn NMR (CDCl 3 ,186 MHz), δ(ppm): 121.73.

Embodiment 2

[0041] Preparation of two (tributyltin) fumarate complexes:

[0042] Add 0.1179g (1mmol) of fumaric acid, 0.6263g (1.05mmol) of bistributyltin oxide, and 37mL of solvent methanol in sequence in a 100ml round bottom flask, and react for 12h at a temperature of 50~65°C; cool , filtered, and under the condition of 20~35°C, control the solvent volatilization and crystallization to obtain a white solid, which is bis(tributyltin)fumarate complex. Yield: 66%, melting point: 125-126°C.

[0043] Elemental analysis (C 28 h 56 o 4 sn 2 ): theoretical value: C, 48.45; H, 8.13. Found: C, 48.40; H, 8.16.

[0044] IR(KBr, cm -1): 2957, 2922, 2872, 2857v(C-H), 1570v as (COO - ), 1377v s (COO - ), 613v(Sn-C), 511v(Sn-O).

[0045] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 6.79(s, 2H, -CH=CH-), 0.90-1.65(m, 54H, Bu-H).

[0046] 13 C NMR (CDCl 3 , 125 MHz), δ (ppm): 170.58 (COO), 134.71 (-CH=CH-), 27.77, 27.03, 16.56, 13.66 (Bu).

[0047] 119 Sn NMR (CDCl 3 ,186 MHz), δ(ppm): 121.73...

Embodiment 3

[0049] Preparation of two (tributyltin) fumarate complexes:

[0050] Add fumaric acid 0.2325g (2mmol), bistributyltin oxide 1.1926 (2mmol), and solvent methanol 60mL in sequence in a 100ml round-bottomed flask, and react at a temperature of 50-65°C for 16 hours; cool and filter , Under the condition of 20~35℃, control the solvent volatilization and crystallization to obtain a white solid, which is bis(tributyltin)fumarate complex. Yield: 64%, melting point: 125-126°C.

[0051] Elemental analysis (C 28 h 56 o 4 sn 2 ): theoretical value: C, 48.45; H, 8.13. Found: C, 48.40; H, 8.16.

[0052] IR(KBr, cm -1 ): 2957, 2922, 2872, 2857v(C-H), 1570v as (COO - ), 1377v s (COO - ), 613v(Sn-C), 511v(Sn-O).

[0053] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): 6.79(s, 2H, -CH=CH-), 0.90-1.65(m, 54H, Bu-H).

[0054] 13 C NMR (CDCl 3 , 125 MHz), δ (ppm): 170.58 (COO), 134.71 (-CH=CH-), 27.77, 27.03, 16.56, 13.66 (Bu).

[0055] 119 Sn NMR (CDCl 3 ,186 MHz), δ(ppm): 121.73.

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Abstract

The invention discloses a bi(tributyltin) trans-butene dibasic acid ester complex as well as a preparation method and an application thereof. The complex is a complex of a structural formula (I) as shown in the specification. The invention further discloses the preparation method the bi(tributyltin) trans-butene dibasic acid ester complex and the application in preparing an anti-tumor medicine.

Description

technical field [0001] The invention relates to a bis(tributyltin)fumarate complex, a preparation method thereof, and an application of the complex in preparing antitumor 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 biological activity of organotin carboxylate complexes is often higher than that...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00
Inventor 朱小明欧亚平邝代治张复兴冯泳兰庾江喜蒋伍玖
Owner HENGYANG NORMAL UNIV
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