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

A synthesis method and compound technology, applied in the field of medicine, can solve the problems of drug resistance, toxic side effects, production cost limitation, low content, etc., and achieve the effect of strong anti-tumor activity and good medicinal value

Inactive Publication Date: 2018-04-20
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 the current research on copper(II) chloride chelates with 1-pyridine-β-carboline as a ligand is still blank

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the compound shown in formula (II) is the synthesis of 1-pyridine-beta-carboline (KL)

[0047] 1) Dissolve 1.60g (10mmol) of tryptamine in 70mL of dichloromethane, then add 1.07g (10mmol) of pyridine-2-carbaldehyde, and heat to reflux for 8 hours; after the reaction, distill under reduced pressure to obtain the crude compound 1 ;

[0048] 2) Dissolve 2.49g (10mmol) of compound 1 in 80mL of glacial acetic acid, then add 13.4g of manganese acetate hydrate (Mn(Ac) 3 ·nH 2 (0), heated to 80°C, reacted overnight, evaporated the solvent, added 100mL water, extracted 3 times with ethyl acetate, combined the organic phases, evaporated the solvent to obtain an oily crude product, and then purified by flash liquid chromatography (V 石油醚 :V 二氯甲烷 =1:1), to obtain light yellow crystal compound 2 (yield about 73%).

[0049] The resulting pale yellow crystals were subjected to proton nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spectrum, elec...

Embodiment 2

[0057] Embodiment 2: the synthesis of ligand KL

[0058] 1) Dissolve 1.60 g (10 mmol) of tryptamine in 70 mL of toluene, then add 1.07 g (10 mmol) of pyridine-2-carbaldehyde, and heat to reflux for 6 hours. After the reaction, distill under reduced pressure to obtain the crude compound 1;

[0059] 2) Dissolve 2.49g (10mmol) of compound 1 in 80mL of glacial acetic acid, then add 13.4g of manganese acetate hydrate (Mn(Ac) 3 ·nH 2 (0), heated to 70°C, reacted overnight, evaporated the solvent, added 100mL water, extracted 3 times with ethyl acetate, combined the organic phases, evaporated the solvent to obtain an oily crude product, and then purified by flash liquid chromatography (V 石油醚 :V 二氯甲烷 =2:3), to obtain light yellow crystal compound 2 (the yield is about 55%).

[0060] The obtained pale yellow crystals were analyzed by H NMR, C NMR, electrospray mass spectrometry and single crystal diffraction, and it was determined to be the target product 1-pyridine-β-carboline.

Embodiment 3

[0061] Embodiment 3: the synthesis of ligand KL

[0062] 1) 1.60g (10mmol) tryptamine is dissolved in the mixed solvent that is made up of the methanol of 30mL and the ethanol of 40mL, then add 1.07g (10mmol) pyridine-2-carboxaldehyde, heat to reflux for 12 hours, after the reaction finishes, reduce Press distillation to obtain crude product compound 1;

[0063] 2) Dissolve 2.49g (10mmol) of compound 1 in 80mL of glacial acetic acid, then add 20mmol of Pb(Ac) 4 , heated to 90°C, reacted overnight, evaporated the solvent, added 100mL of water, extracted 3 times with ethyl acetate, combined the organic phases, evaporated the solvent to obtain an oily crude product, and then purified by flash liquid chromatography (V 石油醚 :V 二氯甲烷 =3:2), the light yellow crystal compound 2 was obtained (the yield was about 67%).

[0064] The obtained pale yellow crystals were analyzed by H NMR, C NMR, electrospray mass spectrometry and single crystal diffraction, and it was determined to be the ...

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Abstract

The invention discloses cupric chloride (II) chelate compounds by using 1-pyridyl-beta-carboline as a ligand, and a synthesis method and application thereof. The structural formula of the cupric chloride (II) chelate compounds is disclosed as Formula (I). The preparation method comprises the following steps: taking compounds disclosed as Formula (II) and cupric chloride dihydrate, dissolving in a polar solvent, and carrying out coordination reaction. The cupric chloride (II) chelate compounds have higher antineoplastic activity than the ligand and cis-platinum, have favorable potential medicinal value, and are expected to prepare various antineoplastic drugs. The Formula (I) and Formula (II) are disclosed as the following structures.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a copper (II) chloride chelate with 1-pyridine-β-carboline as a ligand and 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. [0003] In recent ...

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 彭艳张国海刘彩凤陈胜杨阳
Owner GUANGXI NORMAL UNIV
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