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Method for constructing TNF-alpha inhibitor in one step by using imine as starting material

A technology of α-inhibitors and raw materials, applied in clinical, cell biology, and pharmaceutical fields, can solve the problems of no effective treatment for diseases, etc., and achieve the effect of novel and unique synthetic methods, mild reaction conditions, and excellent yield

Inactive Publication Date: 2019-02-01
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Rheumatoid Arthritis (RA) is an autoimmune disease with a high incidence rate, and there is currently no effective treatment for this disease

Method used

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  • Method for constructing TNF-alpha inhibitor in one step by using imine as starting material
  • Method for constructing TNF-alpha inhibitor in one step by using imine as starting material
  • Method for constructing TNF-alpha inhibitor in one step by using imine as starting material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 0.2 mmol of (E)-N-(2,6-diisopropylphenyl)-1-phenylmethanimine, 0.01 mmol of dichlorodiacetonitrile palladium, and 0.2 mmol of copper oxide into a 25 mL test tube , add toluene and N,N-dimethylformamide as a mixed solvent, the volume ratio is 10:1, add 0.2 mmol of water, then put on a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius for 24 hours . After the TLC (thin layer chromatography) detection reaction, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. The reaction solution was filtered, the filtrate was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain the target product TNF-α inhibitor. The eluent of the column chromatography used was petroleum ether: ethyl acetate with a volume ratio of 10:1 Ester mixed solvent, yield 70%.

[0023] The struc...

Embodiment 2

[0025] Add 0.2 mmol of (E)-N-(2,6-diisopropylphenyl)-1-phenylmethanimine, 0.01 mmol of dichlorodiacetonitrile palladium, and 0.2 mmol of copper oxide into a 25 mL test tube , add toluene as a solvent, add 0.2 mmol of water, and then put on a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius for 24 hours. TLC (thin layer chromatography) tracking detection, no target product was detected.

Embodiment 3

[0027] Add 0.2 mmol of (E)-N-(2,6-diisopropylphenyl)-1-phenylmethanimine, 0.01 mmol of dichlorodiacetonitrile palladium, and 0.2 mmol of copper oxide into a 25 mL test tube , adding N,N-dimethylformamide as a solvent, adding 0.2 mmol of water, and then covering a balloon containing carbon monoxide and oxygen as a carbonyl source, and stirring at 100 degrees Celsius for 24 hours. TLC (thin layer chromatography) tracking detection, no target product was detected.

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Abstract

The invention discloses a method for constructing a TNF-alpha inhibitor in one step by using an imine as a starting material. (E)-N-(2,6-diisopropylphenyl)-1-phenylmethylimine used as a reaction raw material undergoes a carbonylation reaction to form the TNF-alpha inhibitor. The method has the advantages of simple synthesis process, mild reaction conditions and excellent yield.

Description

technical field [0001] The invention relates to the technical fields of medicine, clinic, cell biology, etc., and specifically relates to a synthesis method for constructing TNF-α inhibitor in one step by using imine as a starting material. Background technique [0002] Rheumatoid Arthritis (RA) is an autoimmune disease with a high incidence rate, and there is currently no effective treatment for this disease. As a pro-inflammatory cell molecule, TNF-α plays a very important role in the pathogenesis of RA. Therefore, with the continuous development of biological agents, the use of TNF-α inhibitors in the clinical treatment of RA has been more and more applied. It is precisely because of these application characteristics of TNF-α inhibitors that the synthesis of TNF-α inhibitors has become a research hotspot in the field of new drug development. We used imines as starting materials to construct TNF-α inhibitors in one step, and the synthetic route is as follows: [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 及方华王守才
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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