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Evodiamine derivative, synthetic method and application thereof

A kind of technology of alkaloid derivatives and synthesis method, which is applied in the field of alkaloid derivatives of Evodia rutaecarpa and its synthesis, can solve the problems that the physicochemical properties of anti-tumor drug effects need to be improved, and achieve the goals of inhibiting bacterial growth, high yield, and easy industrial production Effect

Active Publication Date: 2019-05-10
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antitumor efficacy of evodiamine (IC 50 =29μM forMDA-MB-435) and physical and chemical properties need to be improved

Method used

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  • Evodiamine derivative, synthetic method and application thereof
  • Evodiamine derivative, synthetic method and application thereof
  • Evodiamine derivative, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A method for synthesizing alkaloid derivatives of Evodia rutaecarpa, the specific steps are: at room temperature, 213 mg (1 mmol) of the compound of formula (1), 162 mg (1 mmol) of tryptamine, 1-(3-dimethylaminopropyl)- 573 mg (3 mmol) of 3-ethylcarbodiimide hydrochloride, 101 mg (1 mmol) of triethylamine, 12.2 mg (0.1 mmol) of 4-dimethylaminopyridine, dissolved in 10 mL of dichloromethane, reacted for 5 hours, and extracted The product N-(2-(1H-indol-3-yl)ethyl)-2-aminobenzamide (335mg, yield 90%) was obtained by column chromatography.

[0039]Dissolve 444mg (3mmol) of triethyl orthoformate, 355mg (1mmol) of N-(2-(1H-indol-3-yl)ethyl)-2-aminobenzamide, and 70.5mg (0.5mmol) of boron trifluoride ether in 10mL dimethylformamide. The reaction lasted for 5 hours, and the reaction temperature was 100°C. After the reaction was completed, the product 2a was obtained by separation by extraction column chromatography

[0040] (R)-14-phenyl-8,13,13b,14-tetrahydroindolo[2',3':3,...

Embodiment 2

[0044] A method for synthesizing alkaloid derivatives of Evodia rutaecarpa, the specific steps are: at room temperature, 213 mg (1 mmol) of the compound of formula (1), 162 mg (1 mmol) of tryptamine, 1-(3-dimethylaminopropyl)- 573 mg (3 mmol) of 3-ethylcarbodiimide hydrochloride, 101 mg (1 mmol) of triethylamine, 12.2 mg (0.1 mmol) of 4-dimethylaminopyridine, dissolved in 10 mL of dichloromethane, reacted for 5 hours, and extracted The product N-(2-(5-methyl-1H-indol-3-yl)ethyl)-2-(phenylamino)benzamide (348mg, yield 90%) was obtained by column chromatography.

[0045] Triethyl orthoformate 444mg (3mmol),

[0046] N-(2-(5-methyl-1H-indol-3-yl)ethyl)-2-(phenylamino)benzamide369mg (1mmol), boron trifluoride ether 70.5mg (0.5mmol) dissolved in 10mL dimethylformamide . The reaction lasted for 5 hours, and the reaction temperature was 100°C. After the reaction was completed, the product 2 b was obtained by separation by extraction column chromatography

[0047] (R)-10-methyl-14-...

Embodiment 3

[0051] A method for synthesizing alkaloid derivatives of Evodia rutaecarpa, the specific steps are: at room temperature, 213 mg (1 mmol) of the compound of formula (1), 162 mg (1 mmol) of tryptamine, 1-(3-dimethylaminopropyl)- 573 mg (3 mmol) of 3-ethylcarbodiimide hydrochloride, 101 mg (1 mmol) of triethylamine, 12.2 mg (0.1 mmol) of 4-dimethylaminopyridine, dissolved in 10 mL of dichloromethane, reacted for 5 hours, and extracted The product N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-2-(phenylamino)benzamide (362mg, yield 90%) was obtained by column chromatography.

[0052] Triethyl orthoformate 444mg (3mmol),

[0053] N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-2-(phenylamino)benzamide385mg (1mmol), boron trifluoride ether 70.5mg (0.5mmol) dissolved in 10mL dimethylformamide . The reaction lasted for 5 hours, and the reaction temperature was 100°C. After the reaction was completed, the product 2c was separated by extraction column chromatography

[0054] (R)-10-methoxy-14-phenyl-8,13...

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Abstract

The invention discloses an evodiamine derivative. The chemical structural formula is as follows. At cellular level, such a compound has activity equivalent to and even higher than activity of known antitumor active compounds, such as evodiamine. The evodiamine derivative disclosed by the invention has the advantages of mild synthesis condition, insensitivity to water, oxygen, and the like, easilyacquired and low-cost reaction raw materials, simple operation, easiness in separating and purifying products, high yield, easiness in industrial production, and the like. An MTT process is adopted for determining anti-proliferative effect of the evodiamine derivative prepared according to the invention to tumor cell lines and normal cell lines. Such a compound has a novel structure and obvious antitumor activity.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a pharmacologically active alkaloid derivative of Evodia rutaecarpa and its synthesis method and application. Background technique [0002] Malignant tumor is a kind of disease that threatens human health and life. At present, the treatment of malignant tumor usually adopts comprehensive measures combining surgery, radiotherapy and chemotherapy. Chemotherapy is a systemic treatment and can eliminate distantly metastasized cancer cells, so it plays an important role in comprehensive treatment. However, clinical chemotherapy drugs have curative effect, side effects and drug resistance of tumor cells. Therefore, it is still urgent to find anti-tumor drugs with high efficiency and low toxicity from different angles. [0003] The development of bioactive molecules from natural products (NPs) has become an important source of chemical medicines. Among them, evodiamine i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C07D498/14A61P35/00A61P29/00A61P31/04A61P3/04
Inventor 王震谭雯李俊芳邓杰丹张红花
Owner LANZHOU UNIVERSITY
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