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Tricyclohexyltin 2-hydroxy nicotinate complex as well as preparation method and application thereof

A hydroxynicotinate, tricyclohexyl technology, applied in tin organic compounds, chemical instruments and methods, compounds of elements of Group 4/14 of the periodic table, etc., can solve application limitations, no anticancer activity, and anticancer activity problems such as high and low, to achieve the effect of simple preparation method, good anti-cancer activity, and high anti-cancer activity

Inactive Publication Date: 2020-06-09
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 carboxylates is the main factor determining the anticancer activity of the compound. For example, cyclohexyl, n-butyl and phenyltin compounds have stronger anticancer activities, followed by ethyl , the methyl group has almost no anticancer activity, and, because the known organotin compounds generally have strong toxicity, they are limited in application.

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  • Tricyclohexyltin 2-hydroxy nicotinate complex as well as preparation method and application thereof
  • Tricyclohexyltin 2-hydroxy nicotinate complex as well as preparation method and application thereof
  • Tricyclohexyltin 2-hydroxy nicotinate complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of tricyclohexyltin 2-hydroxynicotinate complex:

[0036]In a 250 mL round-bottom flask, add 0.385 g (1 mmol) of tricyclohexyltin hydroxide, 0.1392 g (1 mmol) of 2-hydroxynicotinic acid, and 25 mL of solvent toluene in sequence, and install a Dean-Stark water separator, 112 Heating at -120 °C under reflux for 6 h. After the reaction is completed, filter while hot, and remove the solvent from the filtrate with a rotary evaporator to obtain a white solid, which is recrystallized with methanol, which is tricyclohexyltin 2-hydroxynicotinate complex. Yield: 69%, melting point: 67-69°C.

[0037] Elemental analysis (C 25 h 41 NO 4 Sn): theoretical values: C, 55.78; H, 7.68; N, 2.60. Found: C, 55.72; H, 7.65; N, 2.65.

[0038] IR(KBr, v / cm -1 ): 2918.30 (s), 2846.93 (s), 1678.07 (s), 1658.78 (s), 1629.85 (s), 1595.13 (s), 1571.99 (s), 1467.83 (s), 1444.68 (s), 1388.78 (s ), 1355.96 (s), 1307.74 (m), 1255.66 (m), 1151.50 (m), 1087.85 (w), 1022.27 (m), 991.41 ...

Embodiment 2

[0044] Preparation of tricyclohexyltin 2-hydroxynicotinate complex:

[0045] In a 250 mL round bottom flask, add 0.385 g (1.0 mmol) of tricyclohexyltin hydroxide, 0.1526 g (1.1 mmol) of 2-hydroxynicotinic acid, and 25 mL of solvent toluene in sequence, and install a Dean-Stark water separator , 112-120 ℃ heating and reflux reaction for 8 h. After the reaction is completed, filter while hot, and remove the solvent from the filtrate with a rotary evaporator to obtain a white solid, which is recrystallized with methanol, which is tricyclohexyltin 2-hydroxynicotinate complex. Yield: 69%, melting point: 67-69°C.

[0046] Elemental analysis (C 25 h 41 NO 4 Sn): theoretical values: C, 55.78; H, 7.68; N, 2.60. Found: C, 55.72; H, 7.65; N, 2.65.

[0047] IR(KBr, v / cm -1 ): 2918.30 (s), 2846.93 (s), 1678.07 (s), 1658.78 (s), 1629.85 (s), 1595.13 (s), 1571.99 (s), 1467.83 (s), 1444.68 (s), 1388.78 (s ), 1355.96 (s), 1307.74 (m), 1255.66 (m), 1151.50 (m), 1087.85 (w), 1022.27 (m),...

Embodiment 4

[0053] Preparation of tricyclohexyltin 2-hydroxynicotinate complex:

[0054] In a 250 mL round bottom flask, add 0.7705 g (2.0 mmol) of tricyclohexyltin hydroxide, 0.2918 g (2.1 mmol) of 2-hydroxynicotinic acid, and 50 mL of solvent toluene in sequence, and install a Dean-Stark water separator , 112-120 ℃ heating and reflux reaction for 8 h. After the reaction is completed, filter while hot, and remove the solvent from the filtrate with a rotary evaporator to obtain a white solid, which is recrystallized with methanol, which is tricyclohexyltin 2-hydroxynicotinate complex. Yield: 69%, melting point: 67-69°C.

[0055] Elemental analysis (C 25 h 41 NO 4 Sn): theoretical values: C, 55.78; H, 7.68; N, 2.60. Found: C, 55.72; H, 7.65; N, 2.65.

[0056] IR(KBr, v / cm -1 ): 2918.30 (s), 2846.93 (s), 1678.07 (s), 1658.78 (s), 1629.85 (s), 1595.13 (s), 1571.99 (s), 1467.83 (s), 1444.68 (s), 1388.78 (s ), 1355.96 (s), 1307.74 (m), 1255.66 (m), 1151.50 (m), 1087.85 (w), 1022.27 (m)...

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Abstract

The invention discloses a tricyclohexyltin 2-hydroxy nicotinate complex as well as a preparation method and application thereof. The tricyclohexyltin 2-hydroxy nicotinate complex is a complex represented by the following structural formula (I). The invention also discloses a preparation method of the tricyclohexyltin 2-hydroxy nicotinate complex and an application of the tricyclohexyltin 2-hydroxynicotinate complex in preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a tricyclohexyltin 2-hydroxynicotinate complex, a preparation method thereof, and an application of the complex in preparing antitumor drugs. Background technique [0002] Organotin carboxylates have high biological activity, and have broad application prospects in the fields of sterilization, insecticide, and anticancer drug preparation. Therefore, research on the synthesis, structure and biological activity of organotin carboxylate complexes has been sought by scientists. extensive attention. Existing studies have shown that the hydrocarbon group R in organotin carboxylates is the main factor determining the anticancer activity of the compound. For example, cyclohexyl, n-butyl and phenyltin compounds have stronger anticancer activities, followed by ethyl , the methyl group has almost no anticancer activity, and, because the known organotin compounds generally have strong toxicity, they are limited in application. Regulating...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07F7/2224A61P35/00
Inventor 张复兴朱小明蒋伍玖冯泳兰庾江喜邝代治
Owner HENGYANG NORMAL UNIV