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A kind of alkaloid derivative of Evodia rutaecarpa and its synthesis method and application

An alkaloid derivative and a synthesis method technology are applied in the field of Evodia alkaloid derivatives and their synthesis, which can solve the problems that the physicochemical properties of antitumor efficacy need to be improved, and achieve easy industrial production, mild synthesis conditions and high yield. Effect

Active Publication Date: 2021-06-29
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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  • A kind of alkaloid derivative of Evodia rutaecarpa and its synthesis method and application
  • A kind of alkaloid derivative of Evodia rutaecarpa and its synthesis method and application
  • A kind of alkaloid derivative of Evodia rutaecarpa and its synthesis method and application

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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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PUM

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Abstract

The invention discloses an alkaloid derivative of Evodia rutaecarpa. The chemical structural formula is: This kind of compound has the same or even higher activity than known anticancer active compounds such as evodiamine at the cell level. The alkaloid of Evodia rutaecarpa disclosed in the invention The derivatives are synthesized under mild conditions and are not sensitive to water, oxygen, etc.; the reaction raw materials are readily available and cheap. The method has the advantages of simple operation, easy separation and purification of products, high yield, and easy industrial production. The evodia rutaecarpa alkaloid derivatives prepared in the present invention are tested for their proliferation inhibitory effect on tumor cell lines and normal cell lines by MTT method. The structure of this kind of compound is relatively novel, and its anticancer activity is remarkable.

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 Patents(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