Synthesis, Stereochemistry, and Antimicrobial Activity of 2,6-Diaryl-3-(arylthio)piperidin-4-ones

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概要

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• 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 ^1H, ^<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 ο-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.

• 公益社団法人日本薬学会の論文
• 2006-06-01

著者

• Perumal Subbu

  Department Of Organic Chemistry School Of Chemistry Madurai Kamaraj University

• Srinivasan Murugesan

  Department Of Organic Chemistry School Of Chemistry Madurai Kamaraj University

• SELVARAJ Sangavanaicker

  Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University

• Selvaraj Sangavanaicker

  Department Of Organic Chemistry School Of Chemistry Madurai Kamaraj University

関連論文

• Synthesis, Stereochemistry, and Antimicrobial Activity of 2,6-Diaryl-3-(arylthio)piperidin-4-ones

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