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Synthesis method of ibuprofen ferulate and its application in preparation of immunosuppressive drugs

A ferulic acid ester and drug technology, applied in the field of organic synthesis, can solve problems such as the unexplained anti-tumor mechanism of ibuprofen, and achieve the effect of convenient industrial transformation and simple method

Active Publication Date: 2022-05-20
HENAN UNIV OF CHINESE MEDICINE
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Problems solved by technology

However, the antitumor mechanism of ibuprofen has not been elucidated

Method used

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  • Synthesis method of ibuprofen ferulate and its application in preparation of immunosuppressive drugs
  • Synthesis method of ibuprofen ferulate and its application in preparation of immunosuppressive drugs
  • Synthesis method of ibuprofen ferulate and its application in preparation of immunosuppressive drugs

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Embodiment 1

[0026] The synthetic method of the ibuprofen ferulate of the present embodiment is as follows:

[0027] (1) Add 2.06 g (10 mmol) of ibuprofen, 20 mL of anhydrous dichloromethane and 1 drop of pyridine to the three-necked flask in sequence. Slowly add SOCl dropwise while stirring at room temperature 2 (0.5 mL) of CH 2 Cl 2 Solution 5mL. The temperature of the oil bath was kept at 60° C. and refluxed for 2 hours. Slowly cool the reaction solution afterwards, remove excess SOCl under reduced pressure 2 , spin-dried to obtain a light yellow solid, add 5 mL of anhydrous dichloromethane, and seal it for later use;

[0028] Methanol-derived ester method to check whether the acid chloride was prepared successfully. Take a little methanol into a clean 1.5ml EP tube, add a small amount of ibuprofen acid chloride dropwise and mix well, and confirm that the acid chloride is successfully prepared by TLC spotting;

[0029] (2) Take another three-necked bottle and add 0.194g (1mmol) o...

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Abstract

The invention discloses a method for synthesizing ibuprofen ferulate and its application in preparing immunosuppressive drugs. Slowly add SOCl dropwise to ibuprofen, anhydrous dichloromethane and pyridine under stirring at room temperature. 2 CH 2 Cl 2 Solution, oil bath temperature 55‑65 °C reflux for 2 hours, spin dry to obtain a light yellow solid, add anhydrous dichloromethane to obtain the CH of profenyl chloride 2 Cl 2 solution; cool ferulic acid, tetrahydrofuran and anhydrous dichloromethane in an ice-water bath to 5°C, add triethylamine dropwise, and slowly add the CH of ibuprofenyl chloride dropwise under stirring 2 Cl 2 solution, under ice-water bath, continuously stirred and reacted for 2 h, followed by TLC to detect the reaction, and ibuprofen ferulate was obtained. The ibuprofen ferulate provided by the invention is tested for preliminary in vitro anti-tumor activity by MTT method. The results showed that the inhibitory effect of FI on MCF‑7 cells and HepG2 cells in the range of 50‑400 μmol / L was better than that of ibuprofen.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing ibuprofen ferulate and its application in preparing immunosuppressive drugs. Background technique [0002] Since the structure of salicylic acid was discovered in willow bark, it has been clinically used for many years including non-steroidal anti-inflammatory drugs (NSAIDs) such as aspirin and ibuprofen. Their main mode of action is to inhibit cyclooxygenase (ie, COX-1 and COX-2) leading to a reduction in the synthesis of prostaglandins (messenger molecules in the inflammatory process), thereby achieving analgesic and anti-inflammatory effects. Ibuprofen has been used clinically for many years and is the most widely applicable non-steroidal drug. It can be used to treat general antipyretic and analgesic as well as rheumatoid arthritis and neuritis. [0003] A large number of reports have focused on the research of NSAIDs on tumors...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/14C07C69/612A61P35/00
CPCC07C67/14C07C51/60A61P35/00C07C69/612C07C57/30
Inventor 朱鑫陈坤武香香曾华辉闫敏张岚田启康
Owner HENAN UNIV OF CHINESE MEDICINE
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