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

A synthesis method and caffeic acid ester technology are applied in the synthesis of ibuprofen caffeic acid ester and the application field of preparing immunosuppressive drugs, which can solve the problems such as the unexplained anti-tumor mechanism of ibuprofen, and achieve convenient industrial transformation and inhibition. Proliferation, simple effect

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

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Embodiment 1

[0027] The synthetic method of the ibuprofen caffeate of the present embodiment is as follows:

[0028] (1) Add 3.09g (15mmol) of ibuprofen, 20mL 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;

[0029] 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 acyl chloride dropwise and mix well, and confirm that the acyl chloride is successfully prepared by TLC spotting;

[0030] (2) Take another three-necked bottle and add 0.54g (3mmol) of ca...

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Abstract

The invention discloses a synthesis method of ibuprofen caffeate and its application in the preparation of immunosuppressive drugs. The ibuprofen, anhydrous dichloromethane and pyridine are slowly added dropwise with SOCl under stirring at room temperature. 2 CH 2 Cl 2 Solution, oil bath temperature 55-65 ° C reflux for 2 hours, spin dry, add anhydrous dichloromethane to obtain the CH of ibuprofenyl chloride 2 Cl 2 Solution; cool caffeic acid, DMF and anhydrous dichloromethane in an ice-water bath to 5°C, add triethylamine dropwise, and slowly add CH of ibuprofenyl chloride dropwise under stirring 2 Cl 2 The solution was stirred and reacted in an ice-water bath for 2 h, followed by TLC to detect the reaction to obtain ibuprofen caffeate. The ibuprofen caffeate (CI) provided by the present invention detects its cytotoxicity by the MTT method, and the results show that the inhibitory situation of CI to the proliferation of MCF-7 cells and the proliferation of HepG2 cells is very significant; Induces apoptosis and inhibits proliferation.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing ibuprofen caffeate 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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