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Copper chloride (ii) chelate with 1-pyridine-6-methoxyl-beta-carboline as ligand and its synthesis method and application

A synthetic method and compound technology, applied in the field of medicine, can solve the problems of drug resistance, toxic side effects, insufficient research on β-carboline alkaloids, unfavorable problems, etc., and achieve the effect of strong anti-tumor activity and good potential medicinal value

Inactive Publication Date: 2018-04-10
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
[0005] On the other hand, although cisplatin has been successfully marketed for decades and successfully treated a variety of cancers, clinical results show that it still has some problems, such as drug resistance and toxic side effects, and some cancers naturally show resistance to cisplatin , and some cancers gradually show induced drug resistance after initial treatment
Both preclinical and clinical experiments have shown that non-platinum antitumor drugs have broad prospects for development, but currently the copper (II) chloride chelate with 1-pyridine-6-methoxy-β-carboline as a ligand research is still blank

Method used

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  • Copper chloride (ii) chelate with 1-pyridine-6-methoxyl-beta-carboline as ligand and its synthesis method and application
  • Copper chloride (ii) chelate with 1-pyridine-6-methoxyl-beta-carboline as ligand and its synthesis method and application
  • Copper chloride (ii) chelate with 1-pyridine-6-methoxyl-beta-carboline as ligand and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: The compound shown in formula (II) is the synthesis of 1-pyridine-6-methoxy-β-carboline (LKL)

[0043] 1) Dissolve 100 mg of 5-methoxytryptamine in 40 mL of tetrahydrofuran, stir and add 50 μL of pyridine-2-carbaldehyde dropwise, stir in ice bath for 20 minutes, then add 220 μL of trifluoroacetic acid, react for about 1 hour, remove the ice bath, Continue to react at room temperature for about 1 hour; use thin-layer chromatography (TLC) to track and detect the progress of the reaction. After the reaction is completed, the obtained reactant is adjusted to neutrality with a sufficient amount of ammonia water, and extracted with ethyl acetate, the organic phase is separated, and distillation under reduced pressure is carried out. , to obtain yellow oily liquid, the product of this step is directly used in the next step without purification;

[0044] 2) Add yellow oily liquid to 100mL xylene, then add 200mg 10% Pd / C, heat up to 140°C, reflux reaction, overnigh...

Embodiment 2

[0053] Example 2: Synthesis of Ligand LKL

[0054] 1) Take 100 mg of 5-methoxytryptamine, dissolve it in 60 mL of dichloromethane, stir and add 60 μL of pyridine-2-carbaldehyde dropwise, stir evenly for 10 minutes, add 360 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, extracted with chloroform to separate the organic phase, and distilled under reduced pressure to obtain a yellow oily liquid. The product obtained in this step was directly used in the next step without purification;

[0055] 2) Add the yellow oily liquid to 80mL of anisole, then add 100mg 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 =3:7), yellow crystals were obtained (yield about 55%).

[0056] The obtained yellow crystals...

Embodiment 3

[0057] Example 3: Synthesis of Ligand LKL

[0058] 1) Dissolve 100 mg of 5-methoxytryptamine in 60 mL of tetrahydrofuran, stir and add 40 μL of pyridine-2-carbaldehyde dropwise, stir in ice bath for 15 minutes, then add 120 μL of sulfuric acid, react for about 1 hour, remove the ice bath, and continue at room temperature The reaction is about 0.5h; after the reaction, the obtained reactant is adjusted to alkaline with sufficient amount of ammonia water, and the organic phase is extracted and separated with ethyl acetate, and distilled under reduced pressure to obtain a yellow oily liquid. The product obtained in this step is directly used in the next step without purification. one step reaction;

[0059] 2) Add the yellow oily liquid to 80 mL of anisole, then add 240 mg of 5% Pd / C, heat up to 150 ° C, and reflux for 24 hours; after the reaction, filter the reactant, and filter the cake with methanol, chloroform, acetic acid Ethyl ester was washed 8 times successively, and the...

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Abstract

The invention discloses a copper (II) chloride chelate using 1-pyridyl-6-methoxyl-beta-carboline as a ligand and a synthesis method and application of the copper (II) chloride chelate. The structural formula of the copper (II) chloride chelate is as shown in a formula (I). A preparation method of the copper (II) chloride chelate comprises the following steps: dissolving a compound as shown in a formula (II) and copper chloride dihydrate in a polar solvent; and carrying out a coordination reaction to obtain the final product. The anti-tumor activity of the copper (II) chloride chelate is higher than that of the ligand and cis-platinum, and therefore, the copper (II) chloride chelate has high potential medicinal values, and is expected to be used for preparing various anti-tumor drugs. The structures which are shown in the formula (I) and the formula (II) are as shown in the specification.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a copper (II) chloride chelate compound with 1-pyridine-6-methoxy-β-carboline as a ligand, a synthesis method and application thereof. Background technique [0002] Cancer (also known as malignant tumor) is a systemic and systemic disease involving multiple genes and gradually developing. Statistics show that cancer has become the number one cause of death in quite a few countries and regions, and it is showing a diversified and continuously increasing incidence trend. It is estimated that by 2020, the number of cancer patients worldwide will exceed 20 million, and this trend is developing China is even more serious. How to overcome cancer has become the goal of the medical community. With the development of medical science, people's understanding of tumors is deepening, and every link in the occurrence and development of tumors may become a potential target for treatment. [...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08A61P35/00
CPCC07F1/005
Inventor 彭艳张国海杨阳朱艳宏李亮萍
Owner GUANGXI NORMAL UNIV
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