Method for preparing novel nonsteroidal anti-inflammatory drug and anti-inflammatory and analgesic effects thereof
A compound, the technology of paeonol ester, which is applied in the field of preparation of non-steroidal anti-inflammatory drugs and their anti-inflammatory and analgesic effects, can solve the problems of easy volatility and poor water solubility, instability at room temperature, and low melting point
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Embodiment 1
[0023] Embodiment 1: Synthesis of the synthesis of 5-methoxy-2-acetylphenyl ibuprofen ester (AXC 1 )
[0024] In a 25mL three-necked flask, add ibuprofen (1.03g, 5.0mmol) and thionyl chloride (1.5mL, 20.0mmol), reflux for 2h, and distill off 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 ice bath, and then 10 mL of water was added , dichloromethane extraction (10mL × 3), combined organic phase, successively with saturated NaHCO 3 solution, distilled water and saturated saline solution, anhydrous MgSO 4 dry. After filtration, the filtrate was concentrated and subjected to column chromatography, and the eluent was petroleum ether:ethyl acetate (v:v)=6:1. The eluents were combined, the solvent was evaporated, and the oil pump was pumped to dryness to obtain a light yellow solid with a yield o...
Embodiment 2
[0025] Embodiment 2: the synthesis (AXC 2 )
[0026] In a 25ml round bottom flask, add ketoprofen (1.0g, 4.0mmol), thionyl chloride (1.2mL, 16.0mmol), pyridine 1.0mL, and reflux for 1h. Evaporate excess thionyl chloride under reduced pressure, dissolve the residue in 10 mL of anhydrous dichloromethane, cool in an ice bath, add paeonol (0.60 g, 3.0 mmol) and triethylamine (1.4 mL, 10.0 mL), Stir at room temperature for 3h. Add 0.5N sodium hydroxide solution, continue to stir for 20min, extract with dichloromethane (15mL×3), combine the organic phases, anhydrous MgSO 4 dry. After filtration, the filtrate was concentrated and subjected to column chromatography, and the eluent was petroleum ether:ethyl acetate (v:v)=9:1. The eluents were combined, and the solvent was evaporated to obtain an oily product with a yield of 68.2%. IR (cm -1 , KBr): 1759.2 (C=O), 1643.5 (C=O); 1 HNMR (400MHz, CDCl 3 , TMS), δ: 1.71 (d, 3H, CH 3 ), 2.42 (s, 3H, CH 3 ), 3.80 (s, 3H, CH 3), 4.14...
Embodiment 3
[0027] Embodiment 3: 3-hydroxyl-4-acetylphenyl ibuprofen ester (AXC 3 )
[0028] In a 25mL round bottom flask, 2,4-dihydroxyacetophenone (0.76g, 5.0mmol) was dissolved in 8mL of anhydrous dichloromethane, then added ibuprofen (1.03g, 5.0mmol), DCC (1.03g , 5.0mmol) and several grains of DMAP were stirred until dissolved. After 2h, 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 pump is drained 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=8.0Hz, ArH), 12.40(s, 1H, OH); HR-MS: m / z Calcd for C 21 h 24 o 4 340.1675, Found: 340.1651 (M +...
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