Binuclear copper complex with 9-formyl-10-benzothiazolyl anthracene as a ligand, its synthesis method and application

A synthetic method and compound technology, applied in the field of medicine, can solve problems such as significant toxic and side effects

Active Publication Date: 2021-05-14
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the side effects of platinum drugs are also significant
At present, there are no relevant reports on the binuclear copper complex with 9-formyl-10-benzothiazolyl anthracene as a ligand, its synthesis method and application

Method used

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  • Binuclear copper complex with 9-formyl-10-benzothiazolyl anthracene as a ligand, its synthesis method and application
  • Binuclear copper complex with 9-formyl-10-benzothiazolyl anthracene as a ligand, its synthesis method and application
  • Binuclear copper complex with 9-formyl-10-benzothiazolyl anthracene as a ligand, its synthesis method and application

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Experimental program
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Embodiment 1

[0028] Embodiment 1: Preparation of the compound shown in formula (II) (i.e. 9-formyl-10-benzothianthracene, hereinafter also referred to as ligand)

[0029] 1) Dissolve 5.0mmol of 9,10-anthracenedicarbaldehyde and 6.5mmol of 2-hydrazinobenzothianthracene hydrazone in 100mL of ethanol, reflux reaction at 78°C, and track and detect with TLC until the reaction is complete (about 6h ), the reaction was stopped, and the reaction solution was filtered while it was hot, and the resulting solid was vacuum-dried for 10 h to obtain a mixed product with a yield of 85%;

[0030] 2) Put the resulting mixed product on silica gel column chromatography, elute with a mixed eluent composed of petroleum ether and dichloromethane (volume ratio of petroleum ether and dichloromethane is 1:3), and simultaneously use thin layer chromatography Follow up and monitor, collect the eluate containing the target product, concentrate and dry it to obtain a reddish-brown solid product with a yield of 65%.

...

Embodiment 2

[0038] Embodiment 2: the preparation of compound shown in formula (II)

[0039] Example 1 was repeated, except that in step 2), a mixed eluent composed of petroleum ether and dichloromethane in a volume ratio of 1:7 was used for elution.

[0040] As a result, a reddish-brown solid product was obtained with a yield of 53%.

[0041] The reddish-brown solid product obtained in this embodiment was subjected to infrared spectrum, electrospray mass spectrum, 1 H NMR spectrum and 13 C nuclear magnetic resonance spectrum identification, determined to be the compound shown in formula (II).

Embodiment 3

[0042] Embodiment 3: the preparation of compound shown in formula (II)

[0043] Repeat Example 1, the difference is:

[0044] In step 1), ethanol is replaced with methanol, and the reaction is carried out at 50° C.;

[0045] In step 2), a mixed eluent composed of petroleum ether and dichloromethane in a volume ratio of 1:1 was used for elution.

[0046] As a result, a reddish-brown solid product was obtained with a yield of 36%.

[0047] The reddish-brown solid product obtained in this embodiment was subjected to infrared spectrum, electrospray mass spectrum, 1 H NMR spectrum and 13 C nuclear magnetic resonance spectrum identification, determined to be the compound shown in formula (II).

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Abstract

The invention discloses a binuclear copper complex with 9-formyl-10-benzothiazolyl anthracene as a ligand, a synthesis method and an application thereof. The synthesis method of the copper complex is as follows: react 9-formyl-10-benzothiazolyl anthracene and copper chloride in a polar solvent to obtain the product. The applicant's test results show that the complex has a significant anti-proliferation effect on various tumor cell lines, and its activity is significantly improved compared with the ligand (ligand inactive), and its activity is also significantly higher than that of cisplatin. developed into antitumor drugs. Wherein, the structure of the dinuclear copper complex and 9-formyl-10-benzothiazol-anthrazone as the ligand is as follows formula (I) and formula As shown in (II):

Description

technical field [0001] The invention relates to a binuclear copper complex with 9-formyl-10-benzothiazole anthracene hydrazone as a ligand, a synthesis method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Among the commonly used anticancer chemotherapeutic drugs, anthracyclines represented by Daunorubicin and Doxorubicin occupy an important position, and have been successfully used for decades with remarkable curative effects. Traditional anthracycline anticancer drugs have a characteristic anthraquinone structure, and the anthraquinone structure can generate active oxygen free radicals in vivo, which can cause damage to heart cells or other cells, which is considered to be the reason for their cardiotoxicity. Therefore, it is necessary to further develop new anthracycline derivative anti-tumor compounds based on the anthracycline structure. Among them, it is of great significance to effectively reduce its cardiotoxic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08A61K31/555A61P35/00
CPCA61P35/00C07F1/005
Inventor 梁宏刘延成陈振锋伍颖舒包志春刘瑞雪唐绍园
Owner GUANGXI NORMAL UNIV
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