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 microM vs IC50=1.9 microM of metronidazole).
Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India.
Mohammad
M
Abid
Kakul
K
Husain
Amir
A
Azam
D000563:Amebicides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D004353:Drug Evaluation, Preclinical; D004748:Entamoeba histolytica / Q000187:drug effects; D004987:Ethers / Q000138:chemical synthesis / Q000494:pharmacology; D005663:Furans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis* / Q000494:pharmacology; D011725:Pyridines; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship
D000563:Amebicides; D004987:Ethers; D005663:Furans; D010091:Oximes; D011725:Pyridines; C023666:pyridine; C039281:furan