Cisplatin-like complexes based on 9-imidanthrone hydrazone and their synthesis methods and applications

A technology of complexes and synthesis methods, applied in the fields of compounds containing elements of Group 8/9/10/18 of the periodic table, pharmaceutical formulations, chemical instruments and methods, etc. Problems such as drug resistance, single target and mechanism of action, etc., to achieve the effect of high medicinal value

Inactive Publication Date: 2011-12-07
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, clinical practice shows that cisplatin also has many disadvantages, such as a single target and mechani

Method used

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  • Cisplatin-like complexes based on 9-imidanthrone hydrazone and their synthesis methods and applications
  • Cisplatin-like complexes based on 9-imidanthrone hydrazone and their synthesis methods and applications
  • Cisplatin-like complexes based on 9-imidanthrone hydrazone and their synthesis methods and applications

Examples

Experimental program
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Example Embodiment

[0030] Example 1: Direct synthesis of cis-[Pt by atmospheric solution method II Cl 2 (9-IHA)]

[0031] will K 2 PtCl 4 (1.0 mmol, 0.415 g) and 9-IHA (1.0 mmol, 0.290 g) were dissolved in 5 mL of freshly distilled deoxygenated water and 50 mL of methanol, respectively, and then dissolved K 2 PtCl 4 The aqueous solution of 9-IHA was added dropwise to the methanol solution of 9-IHA, and the reaction was carried out under the protection of nitrogen at 30°C for 48 hours, and a large number of dark brown precipitates were formed, which was the target product. It was cooled and filtered, washed with water, methanol and diethyl ether for several times in turn, placed in a vacuum desiccator, and dried at 30°C to constant weight.

Example Embodiment

[0032] Example 2: Atmospheric pressure solution method to synthesize cis-[Pt II Cl 2 (9-IHA)]

[0033] will Na 2 PtCl 4 (1.0 mmol, 0.400 g) and 9-IHA (1.0 mmol, 0.290 g) were dissolved in 20 mL of H, respectively 2 O and 100 mL of ethanol, the ethanol solution dissolved in 9-IHA was gradually added dropwise to Na 2 PtCl 4 In the aqueous solution, under the protection of light and nitrogen, the reaction was refluxed at 80 °C for 2 hours, and most of the solvent was evaporated. After cooling, a large number of dark brown precipitates were formed, which is the target product. It was cooled and filtered, washed with water, ethanol and acetone for several times in sequence, placed in a blast dryer, and dried at 60°C to constant weight.

Example Embodiment

[0034] Example 3: Synthesis of cis-[Pt through intermediates by atmospheric pressure solution method II Cl 2 (9-IHA)]

[0035] The Pt(II) intermediate cis-[PtCl 2 (DMSO) 2 ] (1.0 mmol, 0.422 g) was dissolved in 30 mL of methanol by heating, 9-IHA (1.0 mmol, 0.290 g) was dissolved in 50 mL of methanol, and then the methanol solution with Pt(II) intermediate was gradually added dropwise to 9- In the methanol solution of IHA, under the protection of nitrogen at 65°C, reflux reaction for 1 hour, after evaporating most of the methanol, cooling to room temperature, a large number of dark brown precipitates are formed, which is the target product. It was cooled and filtered, washed with water, methanol and diethyl ether for several times in turn, placed in a vacuum desiccator, and dried at 40°C to constant weight.

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Abstract

The invention discloses a 9-anthracenecarboxaldehyde-4,5-dihydro-1H-imidazol-2-yl-hydrazone cisplatin complex and a synthesis method and use thereof. In the invention, the two N atoms in 9-anthracenecarboxaldehyde-4,5-dihydro-1H-imidazol-2-yl-hydrazone and a central metal ion Pt(II) are chelated and coordinated to form a chelate having a five-membered ring. Particularly, a direct complexing synthesis method or intermediate complexing synthesis method is adopted. In the technical scheme adopted by the invention, organic alkali 9-IHA having antitumor activity is used as a ligand to coordinate with the Pt(II) to form a complex; and the result of the observation of the activity of the complex for inhibiting the proliferation of human tumor cells and human normal liver cells indicates that the overall in-vitro cell toxicity of the complex is lower than that of a 9-IHA ligand and is similar to that of CDDP (cisplatin), AMSA(amsacrine) and HCPT (hydroxycamptothecine) which are clinic anticancer medicines and that the complex has high potential medical value and can be used in preparation of various antitumor medicines.

Description

technical field [0001] The invention relates to the field of metal coordination compounds, in particular to complexes with 9-imidanthrylhydrazone as a ligand, a synthesis method and application thereof. Background technique [0002] Anthracycline anti-tumor antibiotics are a class of commonly used drugs clinically used in the first-line or second-line standard chemotherapy regimens. Its clinical application has a history of more than 30 years. It occupies an important position. In recent years, my country's domestic production and export-oriented anthracycline drug raw material pharmaceutical enterprises have occupied a large share in the anthracycline drug market, and the production process and output of products are reliably guaranteed. [0003] The anti-tumor activity of anthracyclines is based on their anthracycline mother nucleus: the anthracycline plane can effectively intercalate between adjacent base pairs of DNA molecules, and can form a reversible combination with...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00
Inventor 刘延成陈振锋梁宏程风杰
Owner GUANGXI NORMAL UNIV
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