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Preparation method and application of tricyclohexyltin indole-3-carboxylate complex

A technology of tricyclohexyl and complexes, applied in tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve problems such as application limitation, strong toxicity, etc., and achieve the effects of simple preparation method, low cost, and high anticancer activity

Pending 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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  • Preparation method and application of tricyclohexyltin indole-3-carboxylate complex
  • Preparation method and application of tricyclohexyltin indole-3-carboxylate complex
  • Preparation method and application of tricyclohexyltin indole-3-carboxylate complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of tricyclohexyltin indole-3-carboxylate complex:

[0034] Add 0.3857 g (1 mmol) of tricyclohexyltin hydroxide, 0.1617 g (1 mmol) of indole-3-carboxylic acid, and 10 mL of anhydrous methanol into the microwave reaction tank in sequence. Microwave reaction was performed at 800 W and 100 °C for 60 min. After the reaction, cool naturally, filter, and the solvent volatilizes and crystallizes at room temperature to obtain white crystals, which are tricyclohexyl tin indole-3-carboxylate complexes. Yield: 66%, melting point: 222-225°C.

[0035] Elemental analysis (C27 h 39 NO 2 Sn): theoretical values: C, 61.38; H, 7.44; N, 2.65. Found: C, 61.38; H, 7.43; N, 2.69.

[0036] IR(KBr, v / cm -1 ): 2920.23 (m), 2846.93 (m), 2360.87 (s), 2335.80 (s), 1595.13 (m), 1523.76 (m), 1446.61 (m), 1388.75 (m), 1317.38 (w), 1207.44 (m ), 1122.67 (w), 1037.70 (m), 989.48 (w), 783.10 (w), 742.59 (m), 650.01 (m), 486.06 (m), 420.48 (w).

[0037] 1 H NMR (CDCl 3 , 500 MHz) δ ...

Embodiment 2

[0042] Preparation of tricyclohexyltin indole-3-carboxylate complex:

[0043] Add 0.3846 g (1 mmol) of tricyclohexyltin hydroxide, 0.1693 g (1.05 mmol) of indole-3-carboxylic acid, and 15 mL of anhydrous methanol into the microwave reaction tank in sequence. Microwave reaction was performed at 800 W at 100 °C for 60 min. After the reaction, cool naturally, filter, and the solvent volatilizes and crystallizes at room temperature to obtain white crystals, which are tricyclohexyl tin indole-3-carboxylate complexes. Yield: 67%, melting point: 222-225°C.

[0044] Elemental analysis (C 27 h 39 NO 2 Sn): theoretical values: C, 61.38; H, 7.44; N, 2.65. Found: C, 61.38; H, 7.43; N, 2.69.

[0045] IR(KBr, v / cm -1 ): 2920.23 (m), 2846.93 (m), 2360.87 (s), 2335.80 (s), 1595.13 (m), 1523.76 (m), 1446.61 (m), 1388.75 (m), 1317.38 (w), 1207.44 (m ), 1122.67 (w), 1037.70 (m), 989.48 (w), 783.10 (w), 742.59 (m), 650.01 (m), 486.06 (m), 420.48 (w).

[0046] 1 H NMR (CDCl 3 , 500 MHz)...

Embodiment 3

[0051] Preparation of tricyclohexyltin indole-3-carboxylate complex:

[0052] Add 0.3848 g (1 mmol) of tricyclohexyltin hydroxide, 0.1620 g (1 mmol) of indole-3-carboxylic acid, and 12 mL of anhydrous methanol into the microwave reaction tank in sequence. Microwave reaction was performed at 800 W and 100 °C for 120 min. After the reaction, cool naturally, filter, and the solvent volatilizes and crystallizes at room temperature to obtain white crystals, which are tricyclohexyl tin indole-3-carboxylate complexes. Yield: 68%, melting point: 222-225°C.

[0053] Elemental analysis (C 27 h 39 NO 2 Sn): theoretical values: C, 61.38; H, 7.44; N, 2.65. Found: C, 61.38; H, 7.43; N, 2.69.

[0054] IR(KBr, v / cm -1 ): 2920.23 (m), 2846.93 (m), 2360.87 (s), 2335.80 (s), 1595.13 (m), 1523.76 (m), 1446.61 (m), 1388.75 (m), 1317.38 (w), 1207.44 (m ), 1122.67 (w), 1037.70 (m), 989.48 (w), 783.10 (w), 742.59 (m), 650.01 (m), 486.06 (m), 420.48 (w).

[0055] 1 H NMR (CDCl 3 , 500 MHz) ...

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Abstract

The invention discloses a preparation method and an application of a tricyclohexyltin indole-3-carboxylate complex. The tricyclohexyltin indole-3-carboxylate complex is a complex represented by structural formula (I) shown in the description. The invention also discloses the preparation method of the tricyclohexyltin indole-3-carboxylate complex and the application of the tricyclohexyltin indole-3-carboxylate complex in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a tricyclohexyl tin indole-3-carboxylate complex, a preparation method thereof, and an application of the complex in preparing antitumor drugs. Background technique [0002] Since Brown first discovered organotin carboxylates (CH 3 CO 2 SnPh 3 ) has been shown to inhibit the biological activity of mouse tumors, 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 and biological...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61P35/00A61K31/555
CPCC07F7/2224A61P35/00C07B2200/13
Inventor 朱小明庾江喜张复兴冯泳兰蒋伍玖邝代治谭宇星
Owner HENGYANG NORMAL UNIV
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