Synthesis, characterization, computational calculation and biological studies of some 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives

• Series of 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives were synthesized and characterized.
• 2,6-Diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime compounds were confirmed by IR, NMR and Mass spectroscopy.
• Compound 17 structure is elucidated by single crystal XRD analysis.
• Better antimicrobial activities are observed.

A new series of 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17–24) were designed and synthesized from 2,6-diarylpiperidin-4-one oximes (9–16) with propargyl bromide. Unambiguous structural elucidation has been carried out by investigating IR, NMR (1H, 13C, 1H−1H COSY and HSQC), mass spectral techniques and theoretical (DFT) calculations. Further, crystal structure of compound 17 was evaluated by single crystal X-ray diffraction analysis. Single crystal X-ray structural analysis of compound 17 evidenced that the configuration about CN double bond is syn to C-5 carbon (E-form). The existence of chair conformation was further confirmed by theoretical DFT calculation. All the synthesized compounds were screened for in vitro antimicrobial activity against a panel of selected bacterial and fungal strains using Ciprofloxacin and Ketoconazole as standards. The minimum inhibition concentration (MIC) results revealed that most of the 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17, 19, 20 and 23) exhibited better activity against the selected bacterial and fungal strains.

Figure optionsDownload as PowerPoint slide