Synthesis and antiamoebic activity of new oxime ether derivatives containing 2-acetylpyridine/2-acetylfuran

Various oxime ether derivatives of 2-acetylpyridine and 2-acetylfuran series have been synthesised. O-Alkylation of the oximes by various alkylaminoethyl halides gave the corresponding oxime ether derivatives. The structures of these compounds were elucidated by UV, IR, 1H NMR, 13C NMR spectroscopic methods and elemental analyses. All the compounds were screened in vitro against the HM1:IMSS strain of Entamoeba histolytica. Based on the 50% inhibitory concentration (IC50) data of the 12 compounds evaluated, two of the 2-acetylpyridine series and two in the 2-acetylfuran series showed better IC50 values in vitro when compared with the standard amoebicidal drug, metronidazole. Moreover, one compound showed the most promising antiamoebic activity (IC50 = 0.5 μM vs IC50 = 1.9 μM of metronidazole).

Graphical abstractVarious oxime ether derivatives of 2-acetylpyridine and 2-acetylfuran series have been synthesised. O-Alkylation of oximes by various alkylaminoethyl halides gave the corresponding oxime ether derivatives. The antiamoebic activities of these compounds were evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica. Four compounds showed lower IC50 values than metronidazole. Moreover, compound 6 showed the most promising antiamoebic activity (IC50 = 0.5 μM vs IC50 = 1.9 μM of metronidazole) in the 2-acetylpyridine series.Figure optionsDownload full-size imageDownload as PowerPoint slide