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

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 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.