Synthesis of (2Z)-4,6-Diphenyl-N-((2-(Piperidin-1-yl)Ethyl]-2H-1,3-Thiazin-2-Imino Hydrochloride and its Antimicrobial Activities

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Oluwaseyi Bukky Ovonramwen
Bodunde Joseph Owolabi
Amowie Philip Oviawe


Aim: The study aims to synthesize, characterize, and screen (2Z)-4,6-diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imino hydrochloride for microbial activities.

Methodology: A (2Z)-4,6-diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imino hydrochloride was synthesized via two-steps reaction from chalcone using acetophenone and benzaldehyde, further cyclized with thiourea and later N-alkylated with 1-(2-chloroethyl)piperidine hydrochloride, its purity was tested by thin-layer chromatography (TLC) and characterized by Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (NMR) and nuclear magnetic resonance (13C-NMR) and screened against Pseudomonas aeruginosa, Escherichia coli, Bacillus subtilis, methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Candida albicans using the standard microbiological method.

Results: A golden yellow needle-like crystals (2Z)-4,6-diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imininium hydrochloride with Rf, 7 EtOAc: 3 Pet (0.75) and MP, 285-287oC was synthesized and the in vitro antimicrobial study of the compound exhibited moderate activities in comparison with standard ciprofloxacin and itraconazole.

Conclusion: A new (2Z)-4,6-Diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imininium hydrochloride was synthesized using Claisen-Schmidt condensation, Michael addition and N-alkylation shows moderate antimicrobial activities against E. coli, B. subtilis, methicillin-susceptible S. aureus, methicillin-resistant S. aureus and C. albicans.

Chalcone, thiazine, piperidine, Claisen-schmidt, N-alkylation.

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How to Cite
Ovonramwen, O., Owolabi, B., & Oviawe, A. (2019). Synthesis of (2Z)-4,6-Diphenyl-N-((2-(Piperidin-1-yl)Ethyl]-2H-1,3-Thiazin-2-Imino Hydrochloride and its Antimicrobial Activities. Asian Journal of Physical and Chemical Sciences, 7(3), 1-9.
Original Research Article


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