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19 April 2019
Synthesis and Antimicrobial Activity of Some New Barbituric Acid Derivatives Containing Thiazole Moiety from Sulfadiazine
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A new series of barbituric acid derivatives w prepared and characterized by Fourier-transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H-NMR) and nuclear magnetic resonance (13C-NMR). The antimicrobial studies of synthesized compounds were screened for antibacterial activity against three different types of bacteria (Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), and against two types of fungi (Candida albicans and Aspergillus flavus). In this research, a reaction of sulfadiazine with chloroacetylchloride gave 2-chloro-N-(4-(N-pyrimidin-2-ylsulfamoyl) phenyl) acetamide [A] which was reacted with thiourea, and with K2CO3 to give thiazole derivative [B]. The last compound (thiaole derivative) was reacted with chloroacetyl chloride in basic medium to form compound [R]. 5,5-Diethyl barbituric acid and 5-phenyl,5-ethyl barbituric acid were treated with formaldehyde to give 1,3-bis(hydroxyl methyl)barbituric acids derivatives [B1-B2]. Finally, the compound [R] reacted with 1,3-bis(hydroxyl methyl) barbituric acids derivatives via Williamson reaction to form new barbituric acid derivatives [RB1-RB2]. By the reaction of 5,5-diethyl barbituric acid with 5-phenyl,5-ethyl barbituric acid, new compounds of barbituric acids derivatives [RB3] and [RB4] were obtained. The biological applications of the synthesized compounds showed a greater effect in antimicrobial activities from the starting material (sulfadiazine).
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Synthesis and Antimicrobial Activity of Some New Barbituric Acid Derivatives Containing Thiazole Moiety from Sulfadiazine
Abstract
A new series of barbituric acid derivatives w prepared and characterized by Fourier-transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H-NMR) and nuclear magnetic resonance (13C-NMR). The antimicrobial studies of synthesized compounds were screened for antibacterial activity against three different types of bacteria (Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), and against two types of fungi (Candida albicans and Aspergillus flavus). In this research, a reaction of sulfadiazine with chloroacetylchloride gave 2-chloro-N-(4-(N-pyrimidin-2-ylsulfamoyl) phenyl) acetamide [A] which was reacted with thiourea, and with K2CO3 to give thiazole derivative [B]. The last compound (thiaole derivative) was reacted with chloroacetyl chloride in basic medium to form compound [R]. 5,5-Diethyl barbituric acid and 5-phenyl,5-ethyl barbituric acid were treated with formaldehyde to give 1,3-bis(hydroxyl methyl)barbituric acids derivatives [B1-B2]. Finally, the compound [R] reacted with 1,3-bis(hydroxyl methyl) barbituric acids derivatives via Williamson reaction to form new barbituric acid derivatives [RB1-RB2]. By the reaction of 5,5-diethyl barbituric acid with 5-phenyl,5-ethyl barbituric acid, new compounds of barbituric acids derivatives [RB3] and [RB4] were obtained. The biological applications of the synthesized compounds showed a greater effect in antimicrobial activities from the starting material (sulfadiazine).
References(22)
S.A. Mohammed, H.Y.S. Zebary, Spectrophotometric determination of sulfadiazine via diazotization and coupling reaction - application to pharmaceutical preparations. Raf. J. Sci., 2013, 24(6): 61-73.
V. Kothacota, K.D. Arun, K. Umadevi, et al., Method development and validation of sulphadiazine in bulk and pharmaceutical dosage form by UV-spectrophotometric method. Intern. J. Pharm. Biolog. Arch., 2011, 2(4): 1167-1171.
R.A. Khdur, E.H. Zimam, Synthesis and characterization of some new β-lactam derivatives from azo sulphadiazine and its biological evaluation as anticancer. Oriental Journal of Chemistry, 2018, 34(1): 371-380.
N.A. Patel, S.C. Surti, R.G. Patel, et al., Synthesis, Characterization and biological activity of some new benzoic acid and thiazoloacridine derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 2008, 183: 2191-2203.
G. Vijayta, K. Vinay, A review on biological activity of imidazole and thiazole moieties and their derivatives. Science International, 2013, 1(7): 253-260.
K.T. Mahmudov, M.N. Kopylovich, A.M. Maharramov, et al., Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds. Coordination Chemistry Reviews, 2014, 265: 1-37.
K. Sambasivarao, A.C. Deb, and R.V. Kumar, Spiro-annulation of barbituric acid derivatives and its analogs by ring-closing metathesis reaction. Bioorganic & Medicinal Chemistry Letters, 2005, 15: 1039-1043.
M. Eyad, S. Kamal, E. Jorn, et al., Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives-new synthetic routes and crystal structures. Tetrahedron, 2012, 68: 1005-1010.
A.F. Abbass, E.H. Zimam, Synthesis, characterization and study biological activityof some new pyrimidine and 1, 2, 3, 4-tetrazole derivatives based on sulfadiazine. International Journal of Chem. Tech. Research, 2016, 9(11): 206-217.
N.D. Amnerkar, B.A. Bhongade, and K.P. Bhusari, Synthesis and biological evaluation of some 4-(6-substituted-1,3-benzothiazol-2-yl)amino-1,3-thiazole-2-amines and their Schiff bases. Arabian Journal of Chemistry, 2015, 8: 545-552.
N.D. Amnerkar, K.P. Bhusari, Synthesis of some thiazolylaminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents. Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, 26(1): 22-28.
S.K. Sonwane, S.D. Srivastava, Synthesis and antimicrobial activity of some 2-[(4-substituted-phenyl-3-chloro-azetidin-2-one)-5-(2'-methylamino-4-phenyl-1',3'-thiazolyl-]-1,3,4-thiadiazoles. Journal of Sciences, Islamic Republic of Iran, 2009 20(3): 227-232.
L. Jacek, Polyhydroxyalkyl derivatives and polyetherols obtained from azacyclic compounds. Polimery, 2011, 56(6): 452-460.
P.T. Phan, T.T. Nguyen, H.T. Nguyen, et al., Synthesis and bioactivity evaluation of novel 2-salicyloyl benzofurans as antibacterial agents. Molecules, 2017, 22: 687.
M.R. Shiradkar, G. Mangesh, K.G. Bothara, et al., Synthesis and anticonvulsant activity of clubbed thiazolidinone–barbituric acid and thiazolidinone–triazole derivatives. ARKIVOC, 2007: 58-74.
N.S. Egorove, Antibiotics scientific approach. Mir publishers, Moscow, 1985.
M.G. Al-Mosawy, M.J. Mohamad, Bentonite-based organoclays using chalcone and azo dye as organophilic reagents. Epitoanyag Journal of Silicate Based and Composite Materials, 2017, 2: 49-54.
R.R. Al-Araji, M.S. Mashkour, Spectrophotometric determination of vitamin folic acid B9 in some drugs using 1, 2-naphthoquine-4-sulphonate (NQS). Nano Biomed. Eng. , 2017, 9 (3): 208-213.
F.H. Jabbar, R.F.C. AL-Hamadani, Porous media for removal of organic and inorganic contaminants. Nano Biomed. Eng. , 2018, 10(2): 104-116.
K. Sushil, R.K. Singh, V. Pragati, et al., Synthesis and antimicrobial activity of 2-aminothiazole derivatives. International Journal of Pharmaceutical Sciences and Research, 2010, 1(8): 67-71.
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Acknowledgements
Great thanks to biologist Nadheema Abed Abbas, Department of Ecology, Faculty of Science, University of Kufa for his help in the biological test.
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This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
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