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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.
Ishak EA, El Malah T, Dehbi O, Bakht A, Riadi Y. Novel one-pot synthesis and antimicrobial activity of 2-Amino-4H- 1,3-oxazines and 2-Amino-4H-1,3- Thiazines. J Chem Pharm Res. 2017;9(2): 170-175.
Sivagami S, Ingarsal N. Synthesis and in vitro antimicrobial evaluation of 6-Aryl-4-(1,1'-biphenyl-4-yl)-N-methyl-6H-1,3-thiazin-2-amines. Der Pharma Chem, 2017;9(24):12-14.
Vamsee KRK, Madhusudhan RR. Synthesis, characterization and anthelmintic activity of N-(4-(4-chlorophenyl)-6-phenyl-6H-1,3thiazin-2-yl)-1-(thiophen-2-yl)methanimine derivatives. I JIPSR. 2017;5(05):131-139.
Suganya R, Ganapathi M, Ravi A. Synthesis of substituted bis-thiazine derivatives of imine compounds and its characterization. IJAASR. 2016;1(2):70-74.
Babu K, Selvi D, Pitchai P. Synthesis and microbial studies of novel 1,3-thiazine compounds bearing Schiff base moiety. Der Pharma Chem. 2015;7(10):89-92.
Deshmukh R. Synthesis, structural study and biological evaluation of 1,3-thiazine. Der Chemica Sinica. 2015;6(3):59-63.
Prakash N, Ingarsal N. An efficient synthesis with an antimicrobial screening of N-methyl derivative of 4-(2-bromonaphthalen-6-yl)-6-aryl-6H-1,3-thiazin-2-amines. Der Pharm Chem. 2015; 7(10):246-250.
Sharma PK, Kaur G. Antibacterial, antifungal and antioxidant activities of substituted pyrazolylbenzothiazines. Pharm Lett. 2014;8(11):79-82.
Rathore MM, Rajput PP PR, Parhate VV. Synthesis characterization of some nitro-substituted-1,3-thiazines and their antimicrobial activities. IJSEAS. 2015;1(8): 423-427.
Vadlakonda JB, Murthy MS, Saritha M. Design and synthesis of anti-inflammatory potential of novel quinazoline-4(3H)-ones linked thiazines through amide linkage: docking studies. Int J Chem Sci. 2016;14 (4):3291-3302.
Thakur AS, Deshmukh R, Jha AK, Kumar PS. Synthesis and oral hypoglycemic effect of novel thiazine containing trisubstituted benzenesulfonylurea derivatives. Saudi Pharm. J. 2015;23(5): 475-482.
Bairam R, Srinivasa MM, Afzal BS, Sunil KK. Anticonvulsant evaluation of some novel 1,3-thiazine derivatives. Int J Pharm Sci Res, 2017;8(6):2477-2485.
Ravindar B, Srinivasa MM, Shaik AB. Design, facile synthesis and biological evaluation of novel 1,3-thiazine derivatives as potential anticonvulsant agents. Asian J Pharm Clin Res. 2016;9(5):272-276.
Tony G, Chandran M, Bhat AR, Krishnakumar K. Molecular docking studies: 1,3-thiazine and 1,3-oxazine derivatives. J Pharm Res. 2014;8(2):136-138.
Kawale DS, Vartale SP, Kalyankar BD. Synthesis and antioxidant activity of 6-imino-4-(methylthio)-2-(pyridine-3-yl)-6H-1,3-thiazine-5-carbonitrile. Int Res J Pharm. 2017;8(9):160-164.
Engwa GA, Ayuk EL, Igbojekwe BU, Unaegbu M. Potential antioxidant activity of new tetracyclic and pentacyclic nonlinear phenothiazine derivatives. Biochem Res Int. 2016;8.
Article ID 9896575
Venkatesan K, Satyanarayana VSV, Sivakumar A. Synthesis of pyrimidine carboxamide derivatives catalyzed by uranyl nitrate hexahydrate with their antibacterial and antioxidant studies. Bull Chem Soc Ethiop. 2016;30(1):119-128.
Abdelhamid AO, Shawali AS, Gomha SM, ElEnany WAMA. Synthesis and in vitro anti-breast cancer evaluation of some novel 1,3-thiazines and thiazolone derivatives incorporating pyrazole moiety. World J Pharm Pharm Sci, 2015;4(09): 1695-1705.
Babaiwa UF, Erharuyi O, Falodun A, Akerele JO. Antimicrobial activity of ethyl acetate extract of Citrullus lanatus seeds. Tropical Journal of Pharmaceutical Research. 2017;16(7): 1631-1636.
Pretsch E, B¨uhlmann P, Badertscher M. Structure Determination of Organic Compounds. Springer-Verlag Berlin Heidelberg Fourth Ed. 2009;269-324.
Sawant RL, Bhangale LP, Wadekar JB. Topliss modified approach for design and synthesis of 1,3-Thiazines as Antimicrobials. Int J Drug Discov. 2011;2 (4):637-641.
Baryyan AOA. Enhancement of the cytotoxic activity of some α,β-unsaturated ketones through auxiliary binding. MSc. Thesis, University of Saskatchewan, Saskatoon, Canada. 2012;44.