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9-anthracenecarboxaldehyde-4,5-dihydro-1h-imidazol-2-yl-hydrazone cisplatin complex and synthesis method and use thereof

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, chemical instruments and methods, organic chemistry, etc. Problems such as drug resistance, single target and mechanism of action, etc., to achieve the effect of high medicinal value

Inactive Publication Date: 2013-09-04
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, clinical practice shows that cisplatin also has many disadvantages, such as a single target and mechanism of action, which makes tumor cells prone to drug resistance, and strong neurotoxicity and nephrotoxicity, etc.

Method used

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  • 9-anthracenecarboxaldehyde-4,5-dihydro-1h-imidazol-2-yl-hydrazone cisplatin complex and synthesis method and use thereof
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  • 9-anthracenecarboxaldehyde-4,5-dihydro-1h-imidazol-2-yl-hydrazone cisplatin complex and synthesis method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: direct synthesis of cis-[Pt by normal pressure solution method II Cl 2 (9-IHA)]

[0031] Will K 2 PtCl 4 (1.0mmol, 0.415g) and 9-IHA (1.0mmol, 0.290g) were dissolved in 5mL freshly distilled anaerobic water and 50mL methanol, 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 at 30°C for 48 hours under the protection of nitrogen in the dark, and a large amount of dark brown precipitate was formed, which was the target product. Cool and filter, wash with water, methanol, and diethyl ether several times in small amounts, place in a vacuum desiccator, and dry at 30°C until constant weight.

Embodiment 2

[0032] Embodiment 2: normal pressure solution method synthesis cis-[Pt II Cl 2 (9-IHA)]

[0033] Na 2 PtCl 4 (1.0mmol, 0.400g) and 9-IHA (1.0mmol, 0.290g) were dissolved in 20mL H 2 O and 100mL ethanol, the ethanol solution dissolved with 9-IHA was gradually added dropwise to Na 2 PtCl 4 In the aqueous solution, under the protection of light and nitrogen, reflux at 80°C for 2 hours, and evaporate most of the solvent. After cooling, a large amount of dark brown precipitates are formed, which is the target product. Cool and filter, wash with water, ethanol, and acetone several times successively, place in a blast dryer, and dry at 60°C until constant weight.

Embodiment 3

[0034] Embodiment 3: Atmospheric solution method synthesizes cis-[Pt by intermediate II Cl 2 (9-IHA)]

[0035] The Pt(II) intermediate cis-[PtCl 2 (DMSO) 2 ] (1.0mmol, 0.422g) was heated and dissolved in 30mL of methanol, 9-IHA (1.0mmol, 0.290g) was dissolved in 50mL of methanol, and then the methanol solution of the Pt(II) intermediate was gradually added dropwise to 9- In the methanol solution of IHA, reflux for 1 hour at 65°C in the dark and under the protection of nitrogen. After evaporating most of the methanol, cool to room temperature. A large amount of dark brown precipitates are formed, which is the target product. Cool and filter, wash with water, methanol and diethyl ether several times successively, place in a vacuum desiccator, and dry at 40°C until 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. occupied 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 th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00
Inventor 刘延成陈振锋梁宏程风杰
Owner GUANGXI NORMAL UNIV
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