A series of novel 2,6-diaryl-3-(arylthio)piperidin-4-ones have been synthesized by reaction of arylthioacetones, substituted aromatic aldehydes, and methylamine/ammonium acetate and their structures elucidated by 1 H, 13 C, and 2D NMR (H, H-COSY, C, H-COSY, HMBC, and NOESY) spectroscopy. The NMR data reveal that all these piperidones exist in chair conformation with the 2,6-diaryl groups equatorially oriented, while the arylthio group prefers to be in either an equatorial or axial orientation depending on whether the substituent in the 2,6-diaryl rings is present in 4-or 2-position, respectively. In the case of NH-2,6-diaryl-3-(arylthio)piperidin-4-ones with o-substituted 2,6-diaryl groups, the arylthio group prefers the axial orientation presumably in a bid to minimize the steric and/or electronic repulsion. The arylthiopiperidin-4-ones exhibit significant antibacterial activity against Staphylococcus aureus, Vibrio cholerae, Salmonella typhi, and Escherichia coli and antifungal activity against Candida albicans and Aspergillus niger.
Pyridine derivatives R 0380Synthesis, Stereochemistry, and Antimicrobial Activity of 2,6-Diaryl-3-(arylthio)piperidin-4-ones. -A series of novel 3-arylthiopiperidinone derivatives (20 examples in all) is synthesized via multicomponent reactions and evaluated for antibacterial and antifungal effects. Derivatives (IIIc), (Vb) and (VIIb), show almost the same antibacterial activity as streptomycin and antifungal activity comparable to nystatin.-(SRINIVASAN, M.; PERUMAL*, S.; SELVARAJ, S.; Chem.
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