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A kind of tricyclohexyl tin 2-naphthoate complex and its preparation method and application

A naphthoate, tricyclohexyl technology, applied in the field of tricyclohexyltin 2-naphthoate complexes, can solve the problems of high and low anticancer activity, no anticancer activity, etc., and achieve high and good anticancer activity Anticancer activity, effect of simple preparation method

Active Publication Date: 2019-04-30
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Existing studies have shown that the hydrocarbon group R in organotin is the main factor determining the anticancer activity of the compound. For example, cyclohexyl, n-butyl and phenyltin compounds have strong anticancer activity, followed by ethyl, and methyl almost no anticancer activity

Method used

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  • A kind of tricyclohexyl tin 2-naphthoate complex and its preparation method and application
  • A kind of tricyclohexyl tin 2-naphthoate complex and its preparation method and application
  • A kind of tricyclohexyl tin 2-naphthoate complex and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of tricyclohexyltin 2-naphthoate complex:

[0034] Add 0.172g (1mmol) of naphthoic acid, 0.385g (1mmol) of tricyclohexyltin hydroxide, and 20mL of anhydrous methanol to a 100ml round-bottomed flask in sequence, and react at a temperature of 50-65°C for 8 hours; cool , filter, and control the solvent volatilization and crystallization under the condition of 20~35°C to obtain colorless transparent crystals, which are tricyclohexyltin 2-naphthoate. Yield: 68%, melting point: 205~206°C.

[0035] Elemental analysis (C 30 h 44 o 3 Sn): theoretical value: C, 63.06; H, 7.76. Found: C, 62.91; H, 7.81.

[0036] IR(KBr, v / cm -1 ): 3057, 2918, 2845 v(C-H), 1639 v as (COO - ), 1329v s (COO - ), 605 v(Sn-C), 416 v(Sn-O).

[0037] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H,CH 3 -), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH).

[0038] 13 C NMR (CDCl 3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C),50.91(MeOH), 126.23, 12...

Embodiment 2

[0042] Preparation of tricyclohexyltin 2-naphthoate complex:

[0043] Add 0.172g (1mmol) of naphthoic acid, 0.404g (1.05mmol) of tricyclohexyltin hydroxide, and 37mL of anhydrous methanol to a 100ml round-bottomed flask in sequence, and react at a temperature of 50-65°C for 13 hours; Cool, filter, and control the solvent volatilization and crystallization under the condition of 20~35°C to obtain colorless transparent crystals, which are tricyclohexyltin 2-naphthoate. Yield: 69%, melting point: 205~206°C.

[0044] Elemental analysis (C 30 h 44 o 3 Sn): theoretical value: C, 63.06; H, 7.76. Found: C, 62.91; H, 7.81.

[0045] IR(KBr, v / cm -1 ): 3057, 2918, 2845 v(C-H), 1639 v as (COO - ), 1329v s (COO - ), 605 v(Sn-C), 416 v(Sn-O).

[0046] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H,CH 3 -), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH).

[0047] 13 C NMR (CDCl 3 , 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C),50.91(MeOH), 126.23...

Embodiment 3

[0051] Preparation of tricyclohexyltin 2-naphthoate complex:

[0052] Add 0.518g (3mmol) of naphthoic acid, 1.212g (3.15mmol) of tricyclohexyltin hydroxide, and 63mL of anhydrous methanol to a 100ml round-bottomed flask in sequence, and react at a temperature of 50-65°C for 20 hours; Cool, filter, and control the solvent volatilization and crystallization under the condition of 20~35°C to obtain colorless transparent crystals, which are tricyclohexyltin 2-naphthoate. Yield: 65%, melting point: 205~206°C.

[0053] Elemental analysis (C 30 h 44 o 3 Sn): theoretical value: C, 63.06; H, 7.76. Found: C, 62.91; H, 7.81.

[0054] IR(KBr, v / cm -1 ): 3057, 2918, 2845 v(C-H), 1639 v as (COO - ), 1329v s (COO - ), 605 v(Sn-C), 416 v(Sn-O).

[0055] 1 H NMR (CDCl 3 , 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H,CH 3 -), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH).

[0056] 13 C NMR (CDCl 3 , 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C),50.91(MeOH), 126.23...

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Abstract

The invention discloses a tricyclohexyltin 2-naphthoate complex and a preparation method and application thereof. A structural formula (I) of the complex is as shown in the specification. The invention further discloses a preparation method of the tricyclohexyltin 2-naphthoate complex and application of the tricyclohexyltin 2-naphthoate complex to preparation of antitumor medicines.

Description

technical field [0001] The invention relates to a tricyclohexyltin 2-naphthoate complex, a preparation method thereof, and an application of the tricyclohexyltin 2-naphthoate in preparing antitumor drugs. Background technique [0002] Organotin is a class of metal-organic compounds containing Sn-C bonds, which has high biological activity and has broad application prospects in the fields of sterilization, insecticide, and anticancer drug preparation. Existing studies have shown that the hydrocarbon group R in organotin is the main factor determining the anticancer activity of the compound. For example, the anticancer activity of cyclohexyl, n-butyl and phenyltin compounds is stronger, followed by ethyl, and methyl almost no anticancer activity. The structure of the ligand also plays an important role in the anticancer activity of the complex and the broad spectrum of killing cancer cells. Experiments have proved that the biological activity of organotin carboxylate complexe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07B2200/13C07F7/2224
Inventor 朱小明蒋伍玖邝代治张复兴冯泳兰庾江喜谭宇星
Owner HENGYANG NORMAL UNIV