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Copper chloride complex with 1-(2-pyridinyl)-9-ethyl-beta-carboline ligand and preparation method and application thereof

A synthesis method and compound technology, applied in the field of medicine, can solve problems such as the synthesis method and application of copper chloride that have not yet been seen

Active Publication Date: 2017-03-08
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no relevant reports on the copper (II) chloride complexes and their synthesis methods and applications with 1-(2-pyridine)-9-ethyl-β-carboline as ligands.

Method used

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  • Copper chloride complex with 1-(2-pyridinyl)-9-ethyl-beta-carboline ligand and preparation method and application thereof
  • Copper chloride complex with 1-(2-pyridinyl)-9-ethyl-beta-carboline ligand and preparation method and application thereof
  • Copper chloride complex with 1-(2-pyridinyl)-9-ethyl-beta-carboline ligand and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: The compound shown in formula (II) is the synthesis of 1-(2-pyridine)-9-ethyl-β-carboline (L)

[0045] 1) Add 1.6g (10mmol) tryptamine, 1.1g (10mmol) pyridine-2-carbaldehyde and 50ml toluene into a 150ml round bottom flask, add a water separator and a condenser tube to form a component water reflux device, heat and reflux for 4 hours, wait After the reaction, the solvent was evaporated to dryness, and the residue was recrystallized with 100ml of n-hexane to obtain compound 1 (2.3g, yield 92%);

[0046] 2) Add 2.5g (10mmol) compound 1, 2.5g palladium carbon (10%Pd / C) and 100ml p-xylene to a 250ml round bottom flask, heat to reflux, and use thin layer chromatography to track and detect until the end of the reaction, and let stand Suction filtration and the filtrate was evaporated to dryness, and the resulting residue was purified by silica gel column chromatography (V 石油醚 :V 二氯甲烷 =1:1), to obtain compound 2 (2.1g, yield 86%);

[0047] 3) Add 0.24g (10mmol...

Embodiment 2

[0055] Embodiment 2: the synthesis of ligand L

[0056] Repeat Example 1, the difference is:

[0057] In step 2), with Mn(Ac) 3 Instead of palladium carbon, glacial acetic acid instead of p-xylene, control Mn(Ac) 3 The amount of compound 1 added was twice that of compound 1, and the reaction was carried out at 70°C. TLC was tracked and detected until the end of the reaction, and then the pH of the system was adjusted to 7 with ammonia water, extracted three times with ethyl acetate, and the organic phases were combined. , evaporate the solvent to dryness, and the resulting residue is applied to a silica gel column (chromatographic purification (V 石油醚 :V 二氯甲烷 =1:1), compound 2 was obtained.

[0058] The product obtained in this example was analyzed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance and high-resolution mass spectrometry, and it was determined to be the target product 1-(2-pyridine)-9-ethyl-β-carboline.

Embodiment 3

[0059] Embodiment 3: the synthesis of ligand L

[0060] Repeat Example 2, the difference is:

[0061] In step 2), with Pb(Ac) 4 instead of Mn(Ac) 3 , to control Pb(Ac) 4 The amount of added is 5 times the amount of compound 1, and the reaction is carried out at 60°C.

[0062] The product obtained in this example was analyzed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance and high-resolution mass spectrometry, and it was determined to be the target product 1-(2-pyridine)-9-ethyl-β-carboline.

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Abstract

The invention discloses a copper chloride complex with 1-(2-pyridinyl)-9-ethyl-beta-carboline ligand and a preparation method and application thereof. The structure of the complex is represented as a formula (I), and the preparation method comprises the following steps: copper chloride and a compound of a formula (II) are dissolved in a polar solvent for a coordination reaction and then the product is obtained, wherein the polar solvent is a combination consisting of one or both selected from methanol and ethanol and one or more selected from water, acetone, chloroform, dichloromethane and N,N-dimethyformamide. The complex exhibits a higher antitumor activity than that of the ligand and cisplatin, has a better potential medicinal value and is hopeful to prepare a plurality of antitumor drugs. The structures of formulas (I) and (II) are shown in the description.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a copper chloride complex with 1-(2-pyridine)-9-ethyl-β-carboline as a ligand, a synthesis method and application thereof. Background technique [0002] β-carbolines are a class of alkaloids widely distributed in nature, and they mainly exist in a variety of terrestrial plants and marine organisms. In terms of chemical structure, β-carboline alkaloids belong to indole alkaloids, which are tricyclic ring systems composed of indolopyridines. Atoms exist in different hybridization states, the nitrogen atom at position 9 is sp 3 Hybridization, rich π-electron system, 2-position nitrogen atom is sp 2 Hybridization is a π-electron-deficient system. The two nitrogen atoms are closely related to the chemical properties and biological activities of these compounds. Such compounds have a wide range of biological and pharmacological activities, including: sedative, anxiolytic, hypnotic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08A61K31/555A61P35/00C07D471/04
CPCC07B2200/13C07D471/04C07F1/005
Inventor 陈振锋梁宏刘延成卢幸李亮萍
Owner GUANGXI NORMAL UNIV
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