Synthesis, conformational preferences and antimicrobial evaluation of N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones

• Published in: Journal of molecular structure 2016-09, Vol.1120, p.187-195
• Main Authors: Akila, A., Jeganathan, P., Ponnuswamy, S.
• Format: Article
• Language: English
• Subjects: A1,3-strain; Antiinfectives and antibacterials; Bacteria; Distorted boat conformation; Infrared spectroscopy; Molecular structure; N-Piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones; NMR spectra; Nuclear magnetic resonance; Spectra; Stereochemistry; Synthesis; Two dimensional
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2016.05.028

Five new N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11–15 have been synthesized and characterized using IR, 1H, 13C, DEPT & 2D NMR and mass spectral studies. The NMR spectral data indicate that the N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11–15 prefer to exist in an equilibrium between B1 and B2 conformations. Furthermore, the antibacterial and antifungal studies were carried out. The results show that the piperazinoacetyl piperidin-4-ones 11–15 exhibit good activity against the selected bacterial and fungal strains. A series of N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones have been synthesized and their stereochemistry established. All the synthesized compounds have been evaluated for their antibacterial and antifungal activities and the results reveal a better structure – activity relationship. [Display omitted] •Five piperidin-4-ones were synthesized and conformational analysis was carried out.•Assignment of 1H &13C NMR signals are made using 2D NMR spectra.•All compounds prefer to exist in an equilibrium between B1 and B2 conformations.•Antibacterial and antifungal studies were carried out for all the compounds.•Compounds exhibit good activity against the selected bacterial and fungal strains.