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Divalent platinum complex containing aryl hindering group, preparation method and application thereof

A technology of platinum complexes and steric hindrance, applied in medical preparations containing active ingredients, platinum-group organic compounds, platinum-based organic compounds, etc., can solve problems that limit the application of platinum-based drugs, drug resistance, toxicity, etc.

Inactive Publication Date: 2016-03-02
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of platinum drug has some defects: one is the corresponding toxicity, mainly kidney toxicity and bone marrow toxicity; the other is drug resistance after drug use
These deficiencies limit the application of these platinum drugs to a certain extent

Method used

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  • Divalent platinum complex containing aryl hindering group, preparation method and application thereof
  • Divalent platinum complex containing aryl hindering group, preparation method and application thereof
  • Divalent platinum complex containing aryl hindering group, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1. complex 1 (molecular formula: C 13 h 20 Cl 2 N 2 Pt)

[0034]

[0035] Potassium tetrachloroplatinate (5.00mmol) and ligand (N-benzyl-1R, 2R-cyclohexanediamine, 5.00mmol) were mixed in 80mL of water, stirred at 30°C for 24 hours in the dark, a large amount of yellow precipitate Generated, filtered, washed repeatedly with water, washed with a small amount of ethanol, dried to obtain yellow powder, yield: 86%. IR(KBr,cm -1 ):3466(br),3120,2935,2860,1580,1452,751,702; 1 H-NMR (d 6 -DMSO / TMS,ppm):δ1.09-2.01(m,8H,CH 2 ofDACH),δ2.12-2.25(m,2H,NHCHandNH 2 CH),δ3.91-4.54(m,2H,NHCH 2Ph),δ6.11-6.16(dd,2H,CHNH 2 ),δ7.29-7.31(m,1H,CH 2 NH), δ7.38-8.11(m, 5H, Ar-H); ESI-MS: m / z[M-Cl] + =435(100%).

Embodiment 2

[0038] Embodiment 2. The preparation of complex 2 (molecular formula: C 13 h 19 Cl 2 FN 2 Pt)

[0039]

[0040] Prepared with reference to the method described in Example 1, the ligand is N-(2-fluorobenzyl)-1R,2R-cyclohexanediamine, the reaction temperature is 50°C, and it is stirred for 24 hours in the dark to obtain a light yellow powder. The yield is: 97%. IR(KBr,cm -1 ):3138(br),2933,2862,1579,1494,1451,1229,1187,1139,763; 1 H-NMR (d 6 -DMSO / TMS,ppm):δ0.80-1.85(m,8H,CH 2 ofDACH),δ2.11-2.23(m,2H,NHCHandNH 2 CH),δ3.89-4.40(m,2H,NHCH 2 Ph),δ4.96-5.47(dd,2H,CHNH 2 ), δ6.75-7.45(m, 4H, Ar-H), δ8.89-8.93(m, 1H, CH 2 NH); ESI-MS: m / z [M-Cl] + =453(100%).

Embodiment 3

[0041] The preparation of embodiment 3. complex 3 (molecular formula: C 13 h 19 Cl 2 FN 2 Pt)

[0042]

[0043] Prepared with reference to the method described in Example 1, the ligand is N-(3-fluorobenzyl)-1R,2R-cyclohexanediamine, the reaction temperature is 60°C, and it is stirred for 12 hours in the dark to obtain a light yellow powder. The yield is: 85%. IR(KBr,cm -1 ):3267(br),3188,3100,2938,1587,1451,1258,1147,791,753; 1 HNMR(d 6 -DMSO / TMS,ppm):δ0.76-1.98(m,8H,CH 2 ofDACH),δ1.98-2.23(m,2H,NHCHandNH 2 CH),δ3.67-4.58(m,2H,NHCH2Ph),δ5.01-5.48(dd,2H,CHNH 2 ), δ6.72-7.86(m, 4H, Ar-H), δ8.25-8.27(m, 1H, CH 2 NH); ESI-MS: m / z [M-Cl] + =453(100%).

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Abstract

Disclosed is a antitumor platinum(II) complex with a chiral trans-1,2-cyclohexanediamine derivative containing a sterically hindered aryl group as a ligand, and the structure formula thereof is as shown by formula I or formula II. In formula I, X is 11, OCH3 or F, and is in the ortho, meta or para position to N-methylene in the benzene ring, and Y is chloride ion or iodide ion; In formula II, X is H, OCH3 or F, and is in the ortho, meta or para position to N-methylene in the benzene ring, and Z is oxalate, malonate, 1,1-cyclobutanedicarboxylic acid radical or 3-hydroxy-1,1-cyclobutanedicarboxylic acid radical; The two chiral carbon atoms in trans-1,2-cyclohexanediamine group have the same stereo configuration, and are both R or S configuration. Also disclosed is a method for preparing the platinum complexes, and uses of the platinum complexes for the preparation of antitumor drug.

Description

technical field [0001] The present invention relates to anti-tumor platinum complexes, in particular to anti-tumor platinum (II) complexes with chiral trans-1,2-cyclohexanediamine derivatives containing aryl hindering groups as ligands, and to anti-tumor platinum (II) complexes The preparation method and application of the platinum complex. Background technique [0002] Several anti-tumor platinum drugs including cisplatin, carboplatin and oxaliplatin have been widely used clinically for the treatment of related cancers. However, this type of platinum drug has some defects: first, it exhibits corresponding toxicity, mainly kidney toxicity and bone marrow toxicity; second, it develops drug resistance after administration. These deficiencies limit the application of these platinum drugs to some extent. [0003] In the past ten years, based on the in-depth understanding of the resistance mechanism of platinum complexes, the research on platinum drugs is no longer limited to t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K31/282A61P35/00
CPCA61K31/555A61P35/00C07F15/0093
Inventor 苟少华
Owner SOUTHEAST UNIV
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