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Copper complex with antitumor activity, preparation method thereof and use thereof

A technology of anti-tumor activity and copper complexes, applied in anti-tumor drugs, organic chemical methods, copper organic compounds, etc., to achieve extensive industrial value, high product purity and yield, and efficient induction of tumor cell apoptosis

Inactive Publication Date: 2019-02-22
GUANGXI TEACHERS EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the role of copper in angiogenesis in cancer tissue is not clear, recent X-ray fluorescence studies have demonstrated massive cell migration and massive rearrangement of copper in cells during angiogenesis

Method used

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  • Copper complex with antitumor activity, preparation method thereof and use thereof
  • Copper complex with antitumor activity, preparation method thereof and use thereof
  • Copper complex with antitumor activity, preparation method thereof and use thereof

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Embodiment

[0037] The invention provides a copper complex with antitumor activity and a preparation method thereof.

[0038] The preparation method of the copper complex with antitumor activity comprises the following steps:

[0039] 1. Synthesis of Intermediate A:

[0040] Weigh 2,6-dichloro-3-cyano-4-picoline (0.374g, 2mmol), put it into a 150mL round-bottomed flask, slowly add hydrazine hydrate (0.20g, 4mmol), shake well to make 2, 6-Dichloro-3-cyano-4-methylpyridine was completely dissolved, condensed and refluxed at 120°C for 3 hours, cooled after the reaction, a light yellow solid gradually precipitated, filtered, washed with ice ethanol, and dried to obtain a light yellow intermediate A 0.35 g, yield 93.6%. 1 H NMR (400MHz, d-6 DMSO):11.25(s,1H,Pyrazole-H),7.63(s,1H,Py-H),6.02(s,1H,-NH-),4.79(s,2H,-NH-NH 2 ), 4.09 (s, 2H, Pyrazole–NH 2 ),2.41(s,3H,Py-CH 3 ).

[0041] 2. Synthesis of Ligand L:

[0042] Weigh 1-phenyl-1,3-butanedione (0.50g, 3mmol), dissolve it in 35mL of eth...

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Abstract

The invention provides a copper complex with antitumor activity, a preparation method thereof and application thereof. The copper complex has high antitumor activity and low cytotoxicity, particularlyhas strong killing capability against human bladder transitional cell carcinoma cells (T-24), can efficiently induce tumor cell apoptosis, but has low toxicity in normal human liver cell strains (HL-7702), and is expected to be developed as a novel high-efficiency broad-spectrum low-toxic-and-side-effect cancer chemotherapy drug, thereby being the first invention in the field. The method for synthesizing the copper complex with the antitumor activity is simple and practical, has low cost, good repeatability, high product purity and high yield, has wide industrial value, and is favorable for commercialization and application.

Description

technical field [0001] The present invention relates to the technical field of chemical synthesis, in particular to a copper complex with antitumor activity and a preparation method thereof, and the use of the copper complex for preparing anticancer drugs. Background technique [0002] Metal ions widely present in nature play important roles in environmental, medical, biological, and chemical sciences. Although some of these heavy metals and transition metal ions are low in the organism, most of them exist in the form of metalloproteins and metalloenzymes, and participate in many important reactions, information transmission, and energy transfer in the organism. It has an important influence on the development of metabolism and also occupies an important position in medicinal chemistry. Copper is a trace element required by the human body and plays an important role in the basic physiological processes of various organisms. Copper is the prosthetic group of various enzymes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08C07D471/14A61P35/00
CPCA61P35/00C07B2200/13C07D471/14C07F1/005
Inventor 顾运琼胡飞龙
Owner GUANGXI TEACHERS EDUCATION UNIV