N1-butyrylevodiamine and synthesis method thereof

A technology of butyryl evodiamine and evodiamine, applied in the field of molecular structure and synthesis of N1-butyryl evodiamine

Inactive Publication Date: 2014-09-10
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After inquiring about patents and literature, there is currently no approval for evodiamine N 1 N 1 - Any research report on butyryl evodiamine

Method used

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  • N1-butyrylevodiamine and synthesis method thereof
  • N1-butyrylevodiamine and synthesis method thereof
  • N1-butyrylevodiamine and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Weigh 0.2g of evodiamine (formula II) and place it in a 50ml round-bottomed flask, add 15mL of N,N-dimethylformamide solvent, ultrasonically dissolve, add 0.1323g of sodium hydride (60%) (at this time, evodiamine The molar ratio to sodium hydride is 1:5), after magnetic stirring for 0.5h, add 0.136mL (20°C; density 1.03g / mL) of n-butyryl chloride (formula III) (at this time, evodiamine and n-butyryl chloride The molar ratio is 1:2), the temperature was slowly raised to 70°C, and the reaction was terminated by magnetic stirring for 18 hours; 40 mL of purified water was added to the reaction solution, left to room temperature, and ethyl acetate was added to extract 3 times (40 mL each time). Collect the upper layer extract, add purified water to wash 3 times (each time 50mL), spin dry the solvent, use ethyl acetate:petroleum ether volume ratio of 1:4 solution as eluent, use silica gel column to separate, on silica gel G250 Samples were spotted on thin-layer plates, using ...

Embodiment 2

[0022]Weigh 0.2g of evodiamine (formula II) and place it in a 50ml round-bottomed flask, add 15mL of N,N-dimethylformamide solvent, ultrasonically dissolve, add 0.2630g of sodium hydride (60%) (at this time, evodiamine The molar ratio to sodium hydride is 1:10), after magnetic stirring for 0.5h, add 0.35mL (20°C; density 1.03g / mL) of n-butyryl chloride (formula III) (at this time, evodiamine and n-butyryl chloride The molar ratio is 1:5), the temperature was slowly raised to 80°C, and the reaction was terminated by magnetic stirring for 24 hours; 40 mL of purified water was added to the reaction solution, left to room temperature, and ethyl acetate was added to extract 3 times (40 mL each time). Collect the upper layer extract, add purified water to wash 3 times (50mL each time), remove the solvent by rotary evaporation, use ethyl acetate:petroleum ether with a volume ratio of 1:4 as the eluent, and use a silica gel column to separate. Samples were spotted on G250 thin-layer p...

Embodiment 3

[0024] Weigh 0.2g of evodiamine (formula II) and place it in a 50ml round-bottomed flask, add 15mL of N,N-dimethylformamide solvent, ultrasonically dissolve, add 0.1323g of sodium hydride (60%) (at this time, evodiamine The molar ratio to sodium hydride is 1:5), after magnetic stirring for 0.5h, add 0.401mL (20°C; density 1.03g / mL) of n-butyryl chloride (formula III) (at this time, evodiamine and n-butyryl chloride The molar ratio is 1:6), the temperature was slowly raised to 70°C, and the reaction was terminated by magnetic stirring for 18 hours; 40 mL of purified water was added to the reaction solution, left to room temperature, and ethyl acetate was added to extract 3 times (40 mL each time). Collect the upper layer extract, add purified water to wash 3 times (each time 50mL), spin dry the solvent, use ethyl acetate:petroleum ether volume ratio of 1:4 solution as eluent, use silica gel column to separate, on silica gel G250 Samples were spotted on thin-layer plates, using ...

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Abstract

The invention belongs to the field of chemical synthesis of medicines and relates to a molecular structure of N1-butyrylevodiamine and a synthesis method thereof. The N1-butyrylevodiamine is prepared through the following steps: dissolving evodiamine in a solvent N,N-dimethylformamide, adding sodium hydride and stirring, adding butyryl chloride, continuously stirring after slowly increasing the temperature, adding purified water, extracting by using ethyl acetate, collecting an ethyl acetate extract, washing the extract by using the purified water and carrying out spin-drying to remove the solvent, taking a mixed solvent of petroleum ether and ethyl acetate as an eluting solution, separating by use of a silicagel column, and carrying out spin-drying to remove the solvent, thereby obtaining the N1-butyrylevodiamine.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis and relates to a kind of N 1 -Molecular structure of butyryl evodiamine and its synthesis method. Background technique [0002] Evodiamine is an alkaloid extracted from the dried and nearly mature fruit of Rutaceae plants Evodia rutaecarpa, Evodia bruceae or Shihu. Modern medical research shows that evodiamine has the functions of dilating blood vessels, anti-inflammation, analgesia, warming the stomach and antiemetic , warming the spleen and relieving diarrhea, increasing body temperature, anti-tumor and other pharmacological effects have broad development prospects, but due to the incomplete oral absorption of evodiamine and the low bioavailability, its wide application in clinical practice is limited (Shyr MH , Lin LC, Lin TY. Determination and pharmacokinetics of evodiamine in the plasma and feces of conscious rats. Analytica Chimica Acta, 2006, 558(1 / 2): 16-21). Research rep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14
CPCC07D471/14
Inventor 张景勍胡雪原孙立力万坤谭群友何丹张永红
Owner CHONGQING MEDICAL UNIVERSITY
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