Tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex, and preparation method and application thereof

A furan formate, phenylpropyl technology, applied in tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve problems such as strong toxicity, application limitations, etc., and achieve low cost, simple preparation method, and anticancer activity. high effect

Active Publication Date: 2020-05-12
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because the known organotin compounds generally have strong toxicity, they are limited in application.

Method used

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  • Tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex, and preparation method and application thereof
  • Tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex, and preparation method and application thereof
  • Tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of three (2-methyl-2-phenylpropyl) tin 3-methylbenzofuranoate complexes:

[0033] In a 250 mL round bottom flask, 1.0531 g (1.0 mmol) of bis[tris(2-methyl-2-phenylpropyl)]tin oxide and 0.3528 g of 3-methylbenzofurancarboxylic acid ( 2.0 mmol), solvent toluene 25 mL, install a Dean-Stark trap, and heat at reflux at 112-120 °C for 6 h. After the reaction, filter while it is hot, and remove the solvent from the filtrate with a rotary evaporator to obtain a white solid, which is recrystallized from ethanol, namely tris(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran ester complexes. Yield: 70%, melting point: 112-114°C.

[0034] Elemental analysis (C 40 h 46 o 3 Sn): Theoretical: C, 69.28; H, 6.69. Found: C, 69.32; H, 6.65.

[0035] 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 (㎜), 1145.72 (m), 1076.28 (m), 1029.99 (w), 860.25 (w...

Embodiment 2

[0041] Preparation of three (2-methyl-2-phenylpropyl) tin 3-methylbenzofuranoate complexes:

[0042] In a 250 mL round bottom flask, add bis[tris(2-methyl-2-phenylpropyl)]tin oxide 1.0540 g (1.0 mmol), 3-methylbenzofurancarboxylic acid 0.3880 g (2.2 mmol), solvent toluene 25 mL, install a Dean-Stark trap, and heat at reflux at 112-120 °C for 8 h. After the reaction is completed, filter while it is hot, and remove the solvent from the filtrate with a rotary evaporator to obtain a white solid, which is recrystallized from ethanol, which is tris(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran ester complexes. Yield: 70%, melting point: 112-114°C.

[0043] Elemental analysis (C 40 h 46 o 3 Sn): Theoretical: C, 69.28; H, 6.69. Found: C, 69.32; H, 6.65.

[0044] 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 (㎜), 1145.72 (m), 1076.28 (m), 1029.99 (w), ...

Embodiment 3

[0050] Preparation of three (2-methyl-2-phenylpropyl) tin 3-methylbenzofuranoate complexes:

[0051] In a 250 mL round bottom flask, add bis[tris(2-methyl-2-phenylpropyl)]tin oxide 1.0534 g (1.0 mmol), 3-methylbenzofurancarboxylic acid 0.3885 g (2.2 mmol), 35 mL of solvent toluene, installed a Dean-Stark trap, and heated to reflux at 112-120 °C for 8 h. After the reaction is completed, filter while it is hot, and remove the solvent from the filtrate with a rotary evaporator to obtain a yellow solid, which is recrystallized from ethanol, namely tris(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran ester complexes. Yield: 70%, melting point: 112-114°C.

[0052] Elemental analysis (C 40 h 46 o 3 Sn): theoretical value: C, 69.28; H, 6.69. Found: C, 69.32; H, 6.65.

[0053] 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 (㎜), 1145.72 (m), 1076.28 (m), 10...

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Abstract

The invention discloses a tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex, and a preparation method and an application thereof. The tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex is a complex represented by structural formula (I) shown in the description. The invention further discloses the preparation method of the tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex and the application of the tri(2-methyl-2-phenylpropyl)tin 3-methylbenzofuran carboxylate complex in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a tris(2-methyl-2-phenylpropyl)tin 3-methylbenzofuranoate complex, a preparation method thereof, and an application of the complex in the preparation of antitumor drugs . Background technique [0002] Since Brown first discovered that organotin carboxylate (CH3CO2SnPh3) has the biological activity of inhibiting tumors in mice, the synthesis, structure and biological activity of organotin carboxylate complexes have attracted widespread attention from scientists. However, since the known organotin compounds generally have strong toxicity, their applications are limited. Studies have shown that the structure, reactivity and biological activity of organotin compounds are not only related to the structure of the hydrocarbon group directly connected to the tin atom, but also related to the properties of the ligand. Optimizing the structure of organotin complexes through molecular design to adjust the balance between their toxicity ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00A61K31/555
CPCC07F7/2224A61P35/00C07B2200/13
Inventor 朱小明张复兴蒋伍玖冯泳兰庾江喜邝代治谭宇星
Owner HENGYANG NORMAL UNIV
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