Method for preparing novel nonsteroidal anti-inflammatory drug and anti-inflammatory and analgesic effects thereof
A technology for non-steroidal anti-inflammatory drugs and compounds, which can be used in anti-inflammatory agents, anti-infective drugs, pharmaceutical formulations, etc., and can solve the problems of unstable room temperature storage, easy volatility, poor water solubility and low melting point.
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[0023] Example 1: Synthesis of 5-methoxy-2-acetylphenyl ibuprofen axetil (AXC 1 )
[0024] In a 25 mL three-necked flask, add ibuprofen (1.03 g, 5.0 mmol) and thionyl chloride (1.5 mL, 20.0 mmol), reflux for 2 h, and evaporate the thionyl chloride under reduced pressure. The residue was dissolved in 10 mL of anhydrous dichloromethane, cooled to 0°C in an ice bath, paeonol (0.83 g, 5.0 mmol) and pyridine (0.8 mL, 10.0 mmol) were added, stirred for 2 h under an ice bath, and then 10 mL of water was added , extracted with dichloromethane (10 mL×3), combined the organic phases, successively washed with saturated NaHCO 3 solution, distilled water and saturated brine solution, anhydrous MgSO 4 dry. Filtration, the filtrate was concentrated, and column chromatography was carried out, the eluent was petroleum ether:ethyl acetate (v:v)=6:1. The eluates were combined, the solvent was evaporated, and the oil was pumped to dryness to obtain a pale yellow solid, yield 77.2%, mp 32.0-33...
Example Embodiment
[0025] Example 2: Synthesis of 5-methoxy-2-acetyl phenylketoprofen axetil (AXC 2 )
[0026] In a 25 ml round-bottomed flask, ketoprofen (1.0 g, 4.0 mmol), thionyl chloride (1.2 mL, 16.0 mmol), and 1.0 mL of pyridine were added, and the mixture was refluxed for 1 h. The excess thionyl chloride was evaporated under reduced pressure, the residue was dissolved in 10 mL of anhydrous dichloromethane, cooled in an ice bath, paeonol (0.60 g, 3.0 mmol) and triethylamine (1.4 mL, 10.0 ml) were added, Stir at room temperature for 3h. Add 0.5N sodium hydroxide solution, continue stirring for 20min, extract with dichloromethane (15mL×3), combine the organic phases, anhydrous MgSO 4 dry. Filtration, the filtrate was concentrated, and column chromatography was carried out, the eluent was petroleum ether:ethyl acetate (v:v)=9:1. The eluates were combined and the solvent was evaporated to give an oil in 68.2% yield. IR(cm -1 , KBr): 1759.2 (C=O), 1643.5 (C=O); 1 HNMR (400MHz, CDCl 3 , ...
Example Embodiment
[0027] Example 3: 3-hydroxy-4-acetylphenyl ibuprofen axetil (AXC 3 )
[0028] In a 25mL round-bottom flask, 2,4-dihydroxyacetophenone (0.76g, 5.0mmol) was dissolved in 8mL of anhydrous dichloromethane, and then ibuprofen (1.03g, 5.0mmol), DCC (1.03g) were added. , 5.0 mmol) and DMAP pellets were stirred until dissolved. After 2 hours, filter, concentrate the filtrate, and perform column chromatography. The eluent is petroleum ether:ethyl acetate (v:v)=9:1. The eluents are combined, the solvent is evaporated, and the oil is pumped to dryness to obtain an oily substance, Yield 71.25%. IR(cm -1 , KBr): 3500~3100(OH), 1766.9(C=O), 1643.5(C=O); 1 HNMR (400MHz, CDCl 3 , TMS), δ: 0.80 (d, 6H, CH 3 ), 1.60(d, 3H, CH 3 ), 1.90 (m, 1H, CH), 2.55 (d, 2H, CH) 2 ), 2.72(s, 3H, CH 3 ), 3.80(m, 1H, CH), 6.59(m, 2H, ArH), 7.16(d, 2H, J=7.2Hz, ArH), 7.27(d, 2H, J=7.6Hz, ArH), 7.80( d, 1H, J=8.0 Hz, ArH), 12.40 (s, 1H, OH); HR-MS: m / z Calcd for C 21 H 24 O 4 340.1675, Found: 340.16...
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