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Synthesis, stereochemical and biological studies of some N-cyclohexylcarbamoyl -2,6-diarylpiperidin-4-ones

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Abstract A series of N -cyclohexylcarbamoylpiperidin-4-ones were synthesized by the addition reaction of corresponding piperidin-4-ones with cyclohexylisocyanate in benzene. The structure and stereochemistry of the synthesized N- cyclohexylcarbamoyl -2, 6-diarylpiperidin-4-ones,… Click to show full abstract

Abstract A series of N -cyclohexylcarbamoylpiperidin-4-ones were synthesized by the addition reaction of corresponding piperidin-4-ones with cyclohexylisocyanate in benzene. The structure and stereochemistry of the synthesized N- cyclohexylcarbamoyl -2, 6-diarylpiperidin-4-ones, were established on the basis of their analytical and spectral data (IR, 1 H and 13 C NMR). 2D NMR spectra (HOMOCOSY, HSQC, HMBC and NOESY) were also recorded to analyze the stereochemistry. In the IR spectra of synthesized compounds, the characteristic absorptions due to ring and amide carbonyl functionalities were observed which evidences the formation of N- cyclohexylcarbamoyl-2, 6-diarylpiperidin-4-ones. NMR spectral results are in line with the proposed structure of the compounds synthesized. Conformational analysis was carried out from the extracted coupling constants and NOESY spectral results. The synthesized compounds were evaluated for their antibacterial and antifungal activities.

Keywords: cyclohexylcarbamoyl diarylpiperidin; diarylpiperidin ones; studies cyclohexylcarbamoyl; synthesis stereochemical; biological studies; stereochemical biological

Journal Title: Journal of Molecular Structure
Year Published: 2017

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