Synthesis and anti-inflammatory activity of 1-(2,5-Dihydroxyphenyl)-3-pyridine-2-yl-propenone (AEW-1) compound

Chalcone compounds and some n-hydroxychalcone compounds exhibit anti-inflammatory activity. A chalcone derivative, 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone showed a stronger bond to the COX-2 enzyme than 1-(2,4-dihydroxyphenyl)-3-pyridine-2-il-propenone, 2',5'-dihydroxychalcone, 4-chloro-2', 4'-dihydroxichalcone, and several NSAIDs when they were tested with molecular docking computation using MOE software. The result suggested that compound 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone computationally has better anti-inflammatory activity. Synthesis of the compound was carried out by reacting 2,5-dihydroxyacetophenone and pyridincarbaldehyde (without solvent, K2CO3 catalyst) under microwave radiation (radiation strength of P6 / equivalent to 41oC) within 4 minutes. The purification used ethanol washing: Aquadest (10:90) and ethanol recrystallization. The structure of the synthesized compound was determined by mass spectroscopy, ultraviolet and visible (UV-Vis), infrared (IR), 1H-NMR, 13C-NMR, DEPT, and 2-dimensional NMR spectroscopy (HMQC, COSY, and HMBC). An anti-inflammatory activity test was performed using the rat foot edema method, which was induced by carrageenan. The structural elucidation showed that the compound synthesized was 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone. The compound had a red color, a melting point of 190oC, and a purity of 94 by liquid chromatography. The compound had a DAI (Percentage of Anti-Inflammatory Power) of 50.05 ± 16,244 which was not significantly different from DAI of ibuprofen (57.22 ± 20.134) (p> 0.05). © 2020 The Author(S).