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

Oluwaseyi Bukky Ovonramwen; Bodunde Joseph Owolabi; Amowie Philip Oviawe

doi:10.9734/ajopacs/2019/v7i330096

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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Published: 2019-09-21

DOI: 10.9734/ajopacs/2019/v7i330096

Page: 1-9

Issue: 2019 - Volume 7 [Issue 3]

Oluwaseyi Bukky Ovonramwen *

Department of Chemistry, University of Benin, Benin City, PMB 1154, Area Code 300281, Nigeria.

Bodunde Joseph Owolabi

Department of Chemistry, University of Benin, Benin City, PMB 1154, Area Code 300281, Nigeria.

Amowie Philip Oviawe

Department of Chemistry, University of Benin, Benin City, PMB 1154, Area Code 300281, Nigeria.

*Author to whom correspondence should be addressed.

Abstract

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 R_f, 7 EtOAc: 3 Pet (0.75) and MP, 285-287^oC 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.

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

How to Cite

Ovonramwen, Oluwaseyi Bukky, Bodunde Joseph Owolabi, and Amowie Philip Oviawe. 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. https://doi.org/10.9734/ajopacs/2019/v7i330096.