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Nickel nitrate (ii) chelate with 1-pyridine-6-methoxyl-β-carboline as ligand and its synthesis method and application

A synthesis method and technology of nickel nitrate hexahydrate, applied in the field of medicine, can solve the problems of limited preparation cost, complicated extraction, no synthesis method and application, etc., and achieve the effects of good medicinal value and strong anti-tumor activity.

Inactive Publication Date: 2020-02-28
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, judging from the current research progress, the content of β-carboline alkaloids in natural plants is generally low, and the extraction is relatively complicated, which is not conducive to in-depth research on it. Although it has certain advantages, it is limited by the production cost, so the current research on the expansion of β-carboline alkaloids is still insufficient
However, there is no relevant report on nickel (II) chelate and its synthesis method and application with 1-pyridine-6-methoxyl-β-carboline alkaloid as ligand

Method used

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  • Nickel nitrate (ii) chelate with 1-pyridine-6-methoxyl-β-carboline as ligand and its synthesis method and application
  • Nickel nitrate (ii) chelate with 1-pyridine-6-methoxyl-β-carboline as ligand and its synthesis method and application
  • Nickel nitrate (ii) chelate with 1-pyridine-6-methoxyl-β-carboline as ligand and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: The compound shown in formula (II) is the synthesis of 1-pyridine-6-methoxy-β-carboline (LKL)

[0044] 1) Dissolve 50 mg of 5-methoxytryptamine in 20 mL of tetrahydrofuran, stir and add 25 μL of pyridine-2-carbaldehyde dropwise, stir in ice bath for 20 minutes, then add 110 μL of trifluoroacetic acid, react for about 1 hour, remove the ice bath, Continue the reaction at room temperature for about 1 hour; after the reaction, the obtained reactant is adjusted to neutrality with a sufficient amount of ammonia water, and the organic phase is separated with ethyl acetate, and spin-dried under reduced pressure to obtain a yellow oily liquid, which is directly used in the next step without purification. ;

[0045] 2) Add yellow oily liquid to 50mL xylene, then add 100mg 10% Pd / C, heat up to 140°C, reflux reaction, overnight; after the reaction, filter the reactant, filter cake with methanol, chloroform, acetic acid Ethyl ester was washed 10 times, and the filtra...

Embodiment 2

[0054] Example 2: Synthesis of Ligand LKL

[0055] 1) Take 50 mg of 5-methoxytryptamine, dissolve it in 30 mL of dichloromethane, stir and add 30 μL of pyridine-2-carbaldehyde dropwise, stir evenly for 10 minutes, add 180 μL of acetic acid, and react at room temperature for about 2 hours; The obtained reactant was adjusted to neutrality with a sufficient amount of ammonia water, and the organic phase was separated with chloroform, and spin-dried under reduced pressure to obtain a yellow oily liquid, which was directly used in the next step without purification;

[0056] 2) Add the yellow oily liquid to 40mL of anisole, then add 50mg of 10% Pd / C, heat up to 160°C, and reflux for 20h; Wash 5 times, collect filtrate, filtrate is spin-dried under reduced pressure, obtains crude product, upper fast liquid chromatography afterwards purifies (V 乙酸乙酯 :V 石油醚 =3:9), yellow crystals were obtained (yield about 55%).

[0057] The obtained yellow crystals were analyzed by H NMR, C NMR, e...

Embodiment 3

[0058] Example 3: Synthesis of Ligand LKL

[0059] 1) Dissolve 50 mg of 5-methoxytryptamine in 30 mL of tetrahydrofuran, stir and add 20 μL of pyridine-2-carbaldehyde dropwise, stir in an ice bath for 15 minutes, then add 60 μL of sulfuric acid, react for about 1 hour, remove the ice bath, and continue at room temperature The reaction was about 0.5h; after the reaction, the obtained reactant was adjusted to be alkaline with a sufficient amount of ammonia water, and the organic phase was separated with ethyl acetate, and spin-dried under reduced pressure to obtain a yellow oily liquid, which was directly used in the next step without purification;

[0060] 2) Add the yellow oily liquid to 40mL of anisole, then add 120mg of 5% Pd / C, heat up to 150°C, and reflux for 24h; Ethyl ester was washed 8 times successively, and the filtrate was collected, and the filtrate was spin-dried under reduced pressure to obtain a crude product, which was then purified by flash liquid chromatograph...

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Abstract

The invention discloses a nickel nitrate (II) chelate taking 1-pyridyl-6-methoxyl-beta-carboline as a ligand, as well as a synthesizing method and application of the nickel nitrate (II) chelate. The structural formula of the nickel nitrate (II) chelate is as shown in a formula (I); a preparation method for the nickel nitrate (II) chelate comprises the following steps: dissolving the compound which is as shown in a formula (II) and nickel nitrate hexahydrate in a polar solvent, and performing a complexing reaction to obtain a target product. The nickel nitrate (II) chelate disclosed by the invention shows higher anti-tumour activity than that of the ligand, has a good medicinal value and is expected to be used in preparation of various anti-tumour medicaments. The structures shown in the formula (I) and the formula (II) are as shown in the description.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a nickel (II) nitrate chelate with 1-pyridine-6-methoxy-β-carboline as a ligand and a synthesis method and application thereof. Background technique [0002] Malignant tumor (commonly known as cancer) is one of the main diseases that endanger human health. The formation of cancer is a complex multi-step process, which involves a series of mutations in important regulatory genes. These mutations can lead to rapid growth of cancer cells, damage to healthy organs, and spread to the patient's body in the advanced stage, eventually leading to the death of the patient. The number of people who die from malignant tumors in the world is more than 7 million every year, so the prevention and treatment of cancer can be described as urgent. [0003] Chemotherapy for malignant tumors can be traced back to the 1940s, when it was found that mustard nitrogen (Nitrogenmustard) and folic acid an...

Claims

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Application Information

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IPC IPC(8): C07F15/04C07D471/04A61K31/555A61P35/00
CPCC07D471/04C07F15/045
Inventor 彭艳朱艳宏杨景枚张国海卢幸
Owner GUANGXI NORMAL UNIV
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