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A kind of bis[tris (2-methyl-2-phenyl) propyl tin] 2,2'-biphenyl dicarboxylate complex and its preparation method and application

A technology of biphenyl dicarboxylate and phenylpropyl group is applied in the directions of tin organic compounds, active ingredients of heavy metal compounds, drug combinations, etc., which can solve the problems of no anti-cancer activity and high anti-cancer activity, and achieves low cost, The effect of high anticancer activity and simple preparation method

Active Publication Date: 2019-06-14
HENGYANG NORMAL UNIV
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  • 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 bis[tris (2-methyl-2-phenyl) propyl tin] 2,2'-biphenyl dicarboxylate complex and its preparation method and application
  • A kind of bis[tris (2-methyl-2-phenyl) propyl tin] 2,2'-biphenyl dicarboxylate complex and its preparation method and application
  • A kind of bis[tris (2-methyl-2-phenyl) propyl tin] 2,2'-biphenyl dicarboxylate complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of bis[tris(2-methyl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate:

[0035] Add 0.2427g (1mmol) of 2,2'-biphenyldicarboxylic acid and 1.0529g (1mmol) of bis[tris(2-methyl-2-phenylpropyl)tin] oxide in sequence in a 100ml round bottom flask , solvent ethanol 25mL, react at a temperature of 50-65°C for 8 hours; cool, filter, and control the solvent volatilization and crystallization at 20-35°C to obtain colorless transparent crystals, which are bis[tris(2-formazol yl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate. Yield: 77%, melting point: 124-125°C.

[0036] Elemental analysis (C 74 h 86 o 4 sn 2 ): theoretical value: C, 69.61; H, 6.79. Found: C, 69.65; H, 6.77.

[0037] IR(KBr,v / cm -1 ):3057,3019,2957,2941,2859v(C-H),1680v as (COO - ), 1340v s (COO - ), 556v (Sn-C), 495v (Sn-O).

[0038] 1 H NMR (CDCl 3 ,500MHz), δ(ppm):7.97-6.93(m,38H,Ar-H),1.10(s,36H,CH 3 ),1.06(s,12H,CH 2 Sn),3.71,1.25t(q,t,CH 3 CH 2 OH).

[0039] 13 C NMR (CDCl 3 ...

Embodiment 2

[0043] Preparation of bis[tris(2-methyl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate:

[0044] Add 0.2423g (1mmol) of 2,2'-biphenyldicarboxylic acid and 1.1052g (1.05mmol) of bis[tris(2-methyl-2-phenylpropyl)tin] oxide to a 100ml round bottom flask in sequence ), solvent ethanol 37mL, reacted at a temperature of 50 to 65°C for 8 hours; cooled, filtered, and controlled solvent volatilization and crystallization at a temperature of 20 to 35°C to obtain colorless transparent crystals, namely bis[tris(2- Methyl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate. Yield: 78%, melting point: 124-125°C.

[0045] Elemental analysis (C 74 h 86 o 4 sn 2 ): theoretical value: C, 69.61; H, 6.79. Found: C, 69.65; H, 6.77.

[0046] IR(KBr,v / cm -1 ):3057,3019,2957,2941,2859v(C-H),1680v as (COO - ), 1340v s (COO - ), 556v (Sn-C), 495v (Sn-O).

[0047] 1 H NMR (CDCl 3 ,500MHz), δ(ppm):7.97-6.93(m,38H,Ar-H),1.10(s,36H,CH 3 ),1.06(s,12H,CH 2 Sn),3.71,1.25t(q,t,CH 3 CH 2 OH).

...

Embodiment 3

[0052] Preparation of bis[tris(2-methyl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate:

[0053] Add 0.4832g (2mmol) of 2,2'-biphenyldicarboxylic acid and 2.2118g (2.10mmol) of bis[tris(2-methyl-2-phenylpropyl)tin] oxide in sequence in a 100ml round bottom flask ), solvent ethanol 55mL, reacted at a temperature of 50-65°C for 15h; cooled, filtered, and controlled solvent volatilization and crystallization at 20-35°C to obtain colorless transparent crystals, namely bis[tri(2- Methyl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate. Yield: 76%, melting point: 124-125°C.

[0054] Elemental analysis (C 74 h 86 o 4 sn 2 ): theoretical value: C, 69.61; H, 6.79. Found: C, 69.65; H, 6.77.

[0055] IR(KBr,v / cm -1 ):3057,3019,2957,2941,2859v(C-H),1680v as (COO - ), 1340v s (COO - ), 556v (Sn-C), 495v (Sn-O).

[0056] 1 H NMR (CDCl 3 ,500MHz), δ(ppm):7.97-6.93(m,38H,Ar-H),1.10(s,36H,CH 3 ),1.06(s,12H,CH 2 Sn),3.71,1.25t(q,t,CH 3 CH 2 OH).

[0057] 13 C NMR (CDCl 3 ,...

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Abstract

The invention discloses a bis-[tri-(2-methyl-2-phenyl) tin propyl] 2, 2'-biphenyldicarboxylic acid ester complex, a method for preparing the same and application of the bis-[tri-(2-methyl-2-phenyl) tin propyl] 2, 2'-biphenyldicarboxylic acid ester complex. A structural formula of the bis-[tri-(2-methyl-2-phenyl) tin propyl] 2, 2'-biphenyldicarboxylic acid ester complex is shown. The bis-[tri-(2-methyl-2-phenyl) tin propyl] 2, 2'-biphenyldicarboxylic acid ester complex can be applied to preparing antitumor medicines.

Description

technical field [0001] The invention relates to a bis[tri(2-methyl-2-phenyl)propyltin] 2,2'-biphenyl dicarboxylate complex, a preparation method thereof, and the bis[tri( Application of 2-methyl-2-phenyl)propyltin]2,2'-biphenyl dicarboxylate in the preparation of 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. Experimen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/22A61K31/32A61P35/00
Inventor 朱小明成英杰王一波刘莺张复兴蒋伍玖冯泳兰庾江喜邝代治
Owner HENGYANG NORMAL UNIV
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