title: Synthesis, characterization, computational calculation and biological studies of some 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives.
abstract: 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 ((1)H, (13)C, (1)H-(1)H 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.
authors.affiliation: Department of Chemistry, Annamalai University, Annamalainagar 608002, Tamil Nadu, India.
authors.forename: G
authors.initials: G
authors.lastname: Sundararajan
authors.affiliation: Department of Chemistry, Annamalai University, Annamalainagar 608002, Tamil Nadu, India.
authors.forename: D
authors.initials: D
authors.lastname: Rajaraman
authors.affiliation: CAS in Crystallography and Biophysics, University of Madras, Chennai 600025, Tamil Nadu, India.
authors.forename: T
authors.initials: T
authors.lastname: Srinivasan
authors.affiliation: CAS in Crystallography and Biophysics, University of Madras, Chennai 600025, Tamil Nadu, India.
authors.forename: D
authors.initials: D
authors.lastname: Velmurugan
authors.affiliation: Department of Chemistry, Annamalai University, Annamalainagar 608002, Tamil Nadu, India. Electronic address: krishnasamybala56@gmail.com.
authors.forename: K
authors.initials: K
authors.lastname: Krishnasamy
mesh_terms: D000890:Anti-Infective Agents / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D018360:Crystallography, X-Ray; D004583:Electrons; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory; D055672:Static Electricity
chemical_list: D000890:Anti-Infective Agents; D010091:Oximes; D010881:Piperidones
keywords: 1D-NMR; 2D-NMR spectroscopy; Antimicrobial activities; DFT calculations; Single crystal-XRD