Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound

Abstract

Chalcone compounds and some n-hydroxychalcone compounds exhibit anti-inflammatory activity. Chalcone derivatives 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-prophenone, 2′,5′-dihydroxychalcone, 4-chloro-2′, 4′-dihydroxichalcone, and several NSAIDs when they were tested for molecular docking computing using MOE software. It shows that compounds 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-prophenone. Computationally have better anti-inflammatory activity. Synthesis of compounds was 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). Anti-inflammatory activity test used 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 has a red color, a melting point of 190oC, and a purity of 94% by liquid chromatography. The compound had % 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).