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Preparation method and application of tricyclohexyltin quinoline-6-carboxylate complex

A technology based on hexyltinquinoline and tricyclohexyl, applied in tin organic compounds, pharmaceutical formulations, organic chemical 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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  • Preparation method and application of tricyclohexyltin quinoline-6-carboxylate complex
  • Preparation method and application of tricyclohexyltin quinoline-6-carboxylate complex
  • Preparation method and application of tricyclohexyltin quinoline-6-carboxylate complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of tricyclohexyltinquinoline-6-carboxylate complex:

[0031] Add 0.3857 g (1 mmol) of tricyclohexyl tin hydroxide, 0.1735 g (1 mmol) of quinoline-6-carboxylic acid, and 10 mL of anhydrous methanol as a solvent to the microwave reaction tank in sequence. The microwave reaction was carried out at 800 W and 100 °C for 60 min. After the reaction is completed, it is naturally cooled, filtered, and the solvent is naturally volatilized and crystallized at room temperature to obtain a white crystal, which is a tricyclohexyltinquinoline-6-carboxylate complex. Yield: 62%, melting point: 94-96 °C.

[0032] Elemental Analysis (C 28 H 39 NO 2 Sn): Theoretical: C, 62.24; H, 7.28; N, 2.59. Found: C, 62.22; H, 7.25; N, 2.56.

[0033] IR(KBr, v / cm -1 ): 2920.23 (s), 2846.93 (s), 2362.80 (m), 1602.85 (s), 1498.69 (w), 1446.61 (m), 1365.60 (s), 1313.52 (m), 1172.72 (w), 993.34 (w) ), 906.54 (w), 844.82 (w), 798.53 (s), 640.37 (w), 607.58 (w), 478.35 (w), 416.62 (m).

...

Embodiment 2

[0038] Preparation of tricyclohexyl tin quinoline-6-carboxylate complex:

[0039] Add 0.3846 g (1 mmol) of tricyclohexyltin hydroxide, 0.1823 g (1.05 mmol) of quinoline-6-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 naturally at room temperature to crystallize to obtain white crystals, which are tricyclohexyltinquinoline-6-carboxylate complexes. Yield: 63%, melting point: 94-96 °C.

[0040] Elemental analysis (C 28 h 39 NO 2 Sn): theoretical values: C, 62.24; H, 7.28; N, 2.59. Found: C, 62.22; H, 7.25; N, 2.56.

[0041] IR(KBr, v / cm -1 ): 2920.23 (s), 2846.93 (s), 2362.80 (m), 1602.85 (s), 1498.69 (w), 1446.61 (m), 1365.60 (s), 1313.52 (m), 1172.72 (w), 993.34 (w ), 906.54 (w), 844.82 (w), 798.53 (s), 640.37 (w), 607.58 (w), 478.35 (w), 416.62 (m).

[0042] 1 H NMR (CDCl 3 , 500 MHz)...

Embodiment 3

[0046] Preparation of tricyclohexyl tin quinoline-6-carboxylate complex:

[0047] Add 0.3848 g (1 mmol) of tricyclohexyltin hydroxide, 0.1739 g (1 mmol) of quinoline-6-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 naturally at room temperature to crystallize to obtain white crystals, which are tricyclohexyltinquinoline-6-carboxylate complexes. Yield: 63%, melting point: 94-96 °C.

[0048] Elemental analysis (C 28 h 39 NO 2 Sn): theoretical values: C, 62.24; H, 7.28; N, 2.59. Found: C, 62.22; H, 7.25; N, 2.56.

[0049] IR(KBr, v / cm -1 ): 2920.23 (s), 2846.93 (s), 2362.80 (m), 1602.85 (s), 1498.69 (w), 1446.61 (m), 1365.60 (s), 1313.52 (m), 1172.72 (w), 993.34 (w ), 906.54 (w), 844.82 (w), 798.53 (s), 640.37 (w), 607.58 (w), 478.35 (w), 416.62 (m).

[0050] 1 H NMR (CDCl 3 , 500 MHz) ...

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Abstract

The invention discloses a preparation method and an application of a tricyclohexyltin quinoline-6-carboxylate complex. The tricyclohexyltin quinoline-6-carboxylate complex is a complex represented bystructural formula (I) shown in the description. The invention also discloses the preparation method of the tricyclohexyltin quinoline-6-carboxylate complex and the application of the tricyclohexyltinquinoline-6-carboxylate complex in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a tricyclohexyltinquinoline-6-carboxylate complex, a preparation method thereof, and the application of the complex in the preparation of antitumor drugs. Background technique [0002] Since Brown first discovered organotin carboxylates (CH 3 CO 2 SnPh 3 ) has inhibited the biological activity of mouse tumors, the synthesis, structure and biological activity of organotin carboxylate complexes have received extensive attention from scientists. However, because the known organotin compounds generally have strong toxicity, their application is 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 to the properties of the ligands. Optimizing the structure of organotin complexes by molecular design to adjust the balance between toxicity and biological activity is an impor...

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 朱小明蒋伍玖张复兴冯泳兰邝代治庾江喜谭宇星欧亚平
Owner HENGYANG NORMAL UNIV