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Ruthenium complex of semi-sandwich structure and preparation method thereof

The technology of a ruthenium complex and a sandwich structure is applied in the field of semi-sandwich structure ruthenium complex crystal and its preparation, which can solve problems such as limited complex structure, and achieve the effects of low cost, good repeatability and mild reaction conditions.

Inactive Publication Date: 2018-03-20
SHANGRAO NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Studies have shown that the semi-sandwich structure ruthenium complex has incomparable properties of other complexes, but the available complex structures are very limited

Method used

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  • Ruthenium complex of semi-sandwich structure and preparation method thereof
  • Ruthenium complex of semi-sandwich structure and preparation method thereof
  • Ruthenium complex of semi-sandwich structure and preparation method thereof

Examples

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Effect test

Embodiment 1

[0022] Under the protection of argon, 1,2-dicarbo-closed-dodecaborane (86 mg, 0.6 mmol) was dissolved in 20 mL of anhydrous ether, and n-butyllithium (2.0 mol·L -1 Cyclohexane solution) (0.6mL, 1.2mmol), sulfur powder (38.4mg, 1.2mmol), after stirring and dissolving, add dichloro(p-methylisopropylphenyl) ruthenium (II) dimer (184mg, 0.3mmol) tetrahydrofuran solution 40mL, temperature control 0 ℃, after 4 hours of reaction, the solvent was dried under vacuum; Dissolve the product with 40mL dichloromethane, add 1-phenyl-2-propyn-1-alcohol (158.4 mg, 1.2mmol), temperature controlled at 30°C, stirred and reacted for 12 hours, the reaction solution was concentrated to dryness; the target compound (185.7mg, 45%) was obtained by separation on a 200-300 mesh silica gel column (eluent: V (petroleum ether ) / V (dichloromethane)=1:3); the compound was crystallized with a mixed solvent of n-hexane and tetrahydrofuran to obtain yellow blocky crystals. Melting point: 176°C; 1 H NMR (CDCl ...

Embodiment 2

[0024] Under the protection of argon, 1,2-dicarbo-closed-dodecaborane (86 mg, 0.6 mmol) was dissolved in 20 mL of anhydrous ether, and n-butyllithium (2.0 mol·L -1 Cyclohexane solution) (0.6mL, 1.2mmol), sulfur powder (38.4mg, 1.2mmol), after stirring and dissolving, add dichloro(p-methylisopropylphenyl) ruthenium (II) dimer (184mg, 0.3mmol) tetrahydrofuran solution 40mL, temperature control 0 ℃, after 4 hours of reaction, the solvent was dried under vacuum; Dissolve the product with 40mL dichloromethane, add 1-phenyl-2-propyn-1-alcohol (158.4 mg, 1.2mmol), temperature controlled at 35°C, stirred and reacted for 10 hours, the reaction solution was concentrated to dryness; the target compound (189.8mg, 46%) was obtained by separation on a 200-300 mesh silica gel column (eluent: V (petroleum ether ) / V (dichloromethane)=1:3); the compound was crystallized with a mixed solvent of n-hexane and tetrahydrofuran to obtain yellow blocky crystals. Melting point: 176°C; 1 H NMR (CDCl ...

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Abstract

The invention relates to a ruthenium complex crystal of a semi-sandwich structure and a preparation method thereof and belongs to the technical field of organometallic chemistry. The structure of thecomplex is represented and confirmed by virtue of methods such as single crystal X-ray diffraction and nuclear magnetic resonance, the crystal belongs to a triclinic crystal system, a space group is P-1, a molecular formula is C3OH38B10ORuS2, the molecular weight is 687.89, and cell parameters are described in the specification. 1,2-dicarbon-based-closed-dodecocarborane, n-butyl lithium, sulfur, dichloro(p-methyl isopropyl phenyl) ruthenium (II) dimer and 1-phenyl-2-propyne-1-alcohol are used as raw materials, and column chromatographic separation is adopted, so that the product is obtained. The complex crystal has relatively good chemical stability and solubility, and the preparation method has the advantages of simplicity and high yield, so that the ruthenium complex crystal provided bythe invention has potential drug application value.

Description

technical field [0001] The invention belongs to the technical field of organometallic chemistry, and in particular relates to a semi-sandwich structure ruthenium complex crystal and a preparation method thereof. Background technique [0002] Because the ruthenium complex has low cytotoxicity, it is easy to be absorbed by tumor cells and can be quickly excreted; the affinity with the target can be adjusted conveniently through the change of the ligand; the synthesis technology and method are mature. It is generally believed internationally that ruthenium complexes will become one of the most promising anticancer drugs. Currently, the ruthenium complex ImH[trans-RuCl with good anticancer activity, targeting and low toxicity 4 (DMSO)(Im)] (DMSO: dimethyl sulfoxide, Im: imidazole) (NAMI-A) entered clinical phase II in 2002. [IndH][trans-RuCl, which has a strong killing effect on colon cancer cells 4 Ind 2 ](Ind: indole) (KP 1019) has also completed phase I clinical trials. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00
CPCC07B2200/13C07F15/0046
Inventor 胡久荣刘小刚
Owner SHANGRAO NORMAL UNIV
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