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Tri(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex, and preparation method and application thereof

A technology of phenylpropyl and chlorothiophene, which is applied in tin organic compounds, pharmaceutical formulations, chemical instruments and methods, etc., can solve problems such as application limitations and strong toxicity, and achieve simple preparation methods, low cost, and high anticancer activity Effect

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

AI Technical Summary

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 2-chlorothiophene-5-carboxylate complex, and preparation method and application thereof
  • Tri(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex, and preparation method and application thereof
  • Tri(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]Preparation of tris(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex:

[0033] In a 250 mL round bottom flask, add bis[tris(2-methyl-2-phenylpropyl)]tin oxide 1.0534g (1.0mmol), 2-chlorothiophene-5-carboxylic acid 0.3258g (2.0 mmol), solvent toluene 25 mL, install a Dean-Stark trap, and heat under reflux at 112-120 °C for 6 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 2-chlorothiophene-5-methanol ester complexes. Yield: 85%, melting point: 76-78°C.

[0034] Elemental analysis (C 35 h 41 ClO 2 SSn): Theoretical: C, 61.83; H, 6.08. Found: C, 61.88; H, 6.02.

[0035] IR(KBr, v / cm -1 ): 3728.40 (w), 2958.80 (m), 2920.23 (m), 2897.08 (w), 2860.43 (w), 2360.87 (s), 2337.72 (s), 1635.64 (m), 1537.27 (w), 1492.90 (w ), 1425.40 (m), 1338.60 (m), 1278.81 (w), 1188.15 (w)...

Embodiment 2

[0041] Preparation of tris(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex:

[0042] In a 250 mL round bottom flask, add bis[tris(2-methyl-2-phenylpropyl)]tin oxide 1.0536g (1.0 mmol), 2-chlorothiophene-5-carboxylic acid 0.3582g (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 2-chlorothiophene-5-methanol ester complexes. Yield: 82%, melting point: 76-78°C.

[0043] Elemental analysis (C 35 h 41 ClO 2 SSn): Theoretical: C, 61.83; H, 6.08. Found: C, 61.88; H, 6.02.

[0044] IR(KBr, v / cm -1 ): 3728.40 (w), 2958.80 (m), 2920.23 (m), 2897.08 (w), 2860.43 (w), 2360.87 (s), 2337.72 (s), 1635.64 (m), 1537.27 (w), 1492.90 (w ), 1425.40 (m), 1338.60 (m), 1278.81 (w), 1188.15 (w),...

Embodiment 3

[0050] Preparation of tris(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex:

[0051] In a 250 mL round bottom flask, add bis[tris(2-methyl-2-phenylpropyl)]tin oxide 1.0534 g (1.0 mmol), 2-chlorothiophene-5-carboxylic acid 0.3585 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 white solid, which is recrystallized from ethanol, which is tris(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-methanol ester complexes. Yield: 84%, melting point: 76-78°C.

[0052] Elemental analysis (C 35 h 41 ClO 2 SSn): Theoretical: C, 61.83; H, 6.08. Found: C, 61.88; H, 6.02.

[0053] IR(KBr, v / cm -1 ): 3728.40 (w), 2958.80 (m), 2920.23 (m), 2897.08 (w), 2860.43 (w), 2360.87 (s), 2337.72 (s), 1635.64 (m), 1537.27 (w), 1492.90 (w ), 1425.40 (m), 1338.60 (m), 1278.81 (w), 118...

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Abstract

The invention discloses a tri(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex, and a preparation method and an application thereof. The tri(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-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 2-chlorothiophene-5-carboxylate complex and the application of the tri(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate complex in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a tris(2-methyl-2-phenylpropyl)tin 2-chlorothiophene-5-carboxylate 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00A61K31/381
CPCC07F7/2224A61P35/00
Inventor 朱小明谭宇星蒋伍玖庾江喜张复兴冯泳兰邝代治
Owner HENGYANG NORMAL UNIV