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Bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex and preparation method and application thereof

A technology of nitroisophthalate and nitroisophthalic acid, which is applied in the field of bis[tripropyltin]5-nitroisophthalate complexes, can solve the problem of high and low anticancer activity, No problems such as anti-cancer activity, to achieve the effect of high anti-cancer activity, good anti-cancer activity, and low cost

Active Publication Date: 2017-01-04
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 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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  • Bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex and preparation method and application thereof
  • Bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex and preparation method and application thereof
  • Bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of bis[tri(2-methyl-2-phenyl)propyltin]5-nitroisophthalate complex:

[0034] In a 100ml round bottom flask, add 0.2111g (1mmol) of 5-nitroisophthalic acid, 1.0532g (1mmol) of bis[tri(2-methyl-2-phenylpropyl)tin] oxide, Solvent methanol 30mL, react at a temperature of 50~65°C for 8h; cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain a white solid, which is bis[tris(2-methyl- 2-Phenyl)propyltin]5-nitroisophthalate complex. Yield: 74%, melting point: 139-140°C.

[0035] Elemental analysis (C 68 h 81 NO 6 sn 2 ): theoretical value: C, 65.56; H, 6.55; N, 1.12. Found: C, 65.59; H, 6.51; N, 1.18.

[0036] IR(KBr, v / cm -1 ): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 v as (COO - ), 1304v s (COO - ), 621 v(Sn-C), 557 v(Sn-O).

[0037] 1 H NMR (CDCl 3 , 500 MHz), δ (ppm): 8.90, 8.88(s, 3H, Ar-H), 7.30-7.10(m, 30H, Ar-H), 1.29(s, 12H, CH 2 Sn), 1.25(s, 36H, CH 3 ).

[0038] 13 C NMR (CDCl3 , 125 MHz), δ(p...

Embodiment 2

[0041] Preparation of bis[tri(2-methyl-2-phenyl)propyltin]5-nitroisophthalate complex:

[0042] In a 100ml round bottom flask, add 0.2116g (1mmol) of 5-nitroisophthalic acid and 1.1060g (1.05mmol) of bis[tri(2-methyl-2-phenylpropyl)tin] oxide in sequence 1. Solvent methanol 47mL, react at a temperature of 50~65°C for 12h; cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a white solid, which is bis[tris(2-methyl -2-phenyl)propyltin]5-nitroisophthalate complex. Yield: 76%, melting point: 139-140°C.

[0043] Elemental analysis (C 68 h 81 NO 6 sn 2 ): theoretical value: C, 65.56; H, 6.55; N, 1.12. Found: C, 65.59; H, 6.51; N, 1.18.

[0044] IR(KBr, v / cm -1 ): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 v as (COO - ), 1304v s (COO - ), 621 v(Sn-C), 557 v(Sn-O).

[0045] 1 H NMR (CDCl 3 , 500 MHz), δ (ppm): 8.90, 8.88(s, 3H, Ar-H), 7.30-7.10(m, 30H, Ar-H), 1.29(s, 12H, CH 2 Sn), 1.25(s, 36H, CH 3 ).

[0046] 13 C N...

Embodiment 3

[0049] Preparation of bis[tri(2-methyl-2-phenyl)propyltin]5-nitroisophthalate complex:

[0050] Add 0.4218g (2mmol) of 5-nitroisophthalic acid and 2.2112g (2.1mmol) of bis[tri(2-methyl-2-phenylpropyl)tin] oxide in sequence in a 100ml round bottom flask 1. Solvent methanol 63mL, react at a temperature of 50~65°C for 18h; cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a white solid, which is bis[tris(2-methyl -2-phenyl)propyltin]5-nitroisophthalate complex. Yield: 72%, melting point: 139-140°C.

[0051] Elemental analysis (C 68 h 81 NO 6 sn 2 ): theoretical value: C, 65.56; H, 6.55; N, 1.12. Found: C, 65.59; H, 6.51; N, 1.18.

[0052] IR(KBr, v / cm -1 ): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 v as (COO - ), 1304v s (COO - ), 621 v(Sn-C), 557 v(Sn-O).

[0053] 1 H NMR (CDCl 3 , 500 MHz), δ (ppm): 8.90, 8.88(s, 3H, Ar-H), 7.30-7.10(m, 30H, Ar-H), 1.29(s, 12H, CH 2 Sn), 1.25(s, 36H, CH 3 ).

[0054] 13 C NMR...

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Abstract

The invention discloses a bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex and a preparation method and application thereof. The structural formula of the complex is shown in the description. The invention further discloses a preparation method for the bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex and application of the bis [tris (2-methyl-2-phenyl) propyl-tin] 5-nitro-isophthalate complex in preparing antitumor drugs.

Description

technical field [0001] The invention relates to a bis[tri(2-methyl-2-phenyl)propyl tin] 5-nitroisophthalate complex, a preparation method thereof, and the use of the complex in the preparation of antitumor drugs in the application. 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 or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07F7/2224
Inventor 朱小明邝代治张复兴冯泳兰庾江喜蒋伍玖谭宇星杨春林
Owner HENGYANG NORMAL UNIV
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