Synthesis and Spectroscopic Studies of Alkyl Substituted Thiourea Derivatives Towards the Selected Antibacterial Activities
Keywords:
spectroscopic, isobutyryl, pivaloyl, alkyl-thioureas, antibacterial agentAbstract
In this study, new members of alkyl substituted thiourea derivatives of (R-C(O)NHC(S)NHCH2CH(CH3)NHC(S)NHC(O)-R) in which R represents alkyl group namely isobutyryl and pivaloyl were successfully synthesized for their antibacterial activities. The compounds were spectroscopically and analytically characterized via infrared (IR) spectroscopy, ultraviolet–visible (UV–vis) spectroscopy, CHNS elemental analysis as well melting point analysis. In turn, they were screened for antibacterial activity using selected bacteria namely, Micrococcus sp., Salmonella typhi, Aeromonas sp., Klebsiella pneumoniae, Bacillus cereus and also Escherichia coli. From the antibacterial test, all synthesized compounds were found to exhibit great potential results as antibacterial agents, except for 1which did not show inhibition activity towards Klebsiella pneumoniae. Thus, these proposed molecular structures have given ideal indication to act as antibacterial agents which have utmost potential in pharmaceutical and medical industries in the near future.
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References
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Arslan, H., Flörke, U., & Külcü, N. (2004). The crystal and molecular structure of 1-(2-chloro-benzoyl)-3-ptolyl-
thiourea. Turkish Journal of Chemistry, 28(6), 673-678.
Binzet, G., Arslan, H., Flörke, U., Külcü, N., & Duran, N. (2006). Synthesis, characterization and antimicrobial
activities of transition metal complexes of N, N-dialkyl-N′-(2-chlorobenzoyl) thiourea derivatives. Journal of
Coordination Chemistry, 59(12), 1395-1406.
Douglass, I. B., & Dains, F. B. (1934). Some Derivatives of Benzoyl and Furoyl Isothiocyanates and their Use
in Synthesizing Heterocyclic Compounds. Journal of the American Chemical Society, 56(3), 719-721.
Emen, M. F., Arslan, H., Külcü, N., Flörke, U., & Duran, N. (2005). Synthesis, characterization and antimicrobial activities of some metal complexes with N'-(2-chloro-benzoyl) thiourea ligands: The crystal structure of fac-[CoL3] and cis-[PdL2]. Polish Journal of Chemistry, 79(10), 1615-1626.
Ghazali, S. R., Khairul, W. M., & Shamsuddin, M. (2013). Synthesis and Characterisation of Palladium (II)
Complex of (N-Pentanoulthioreodp)-N’-Propanoic Acid and Its Application as Catalyst in Heck Cross Coupling
Reaction. Australian Journal of Basic and Applied Sciences, 7(9), 149-155.
Jasman, S. M., Khairul, W. M., Tagg, T., KuBulat, K., Rahamathullah, R., Arshad, S., Razak, I. A., & Tahir, M. I. M. (2015). Synthesis, Crystal Structure and Electrical Studies of Naphthoyl-Thiourea as Potential Organic Light Emitting Diode. Journal of Chemical Crystallography, 45(7), 338-349.
Karakuş, S., & Rollas, S. (2002). Synthesis and antituberculosis activity of new N-phenyl-N′-[4-(5- alkyl/arylamino-1, 3, 4-thiadiazole-2-yl) phenyl] thioureas. Il Farmaco, 57(7), 577-581.
Karipcin, F., Atis, M., Sariboga, B., Celik, H., & Tas, M. (2013). Structural, spectral, optical and antimicrobial
properties of synthesized 1-benzoyl-3-furan-2-ylmethyl-thiourea. Journal of Molecular Structure, 1048, 69-77.
Kavak, G., Özbey, S., Binzet, G., & Külcü, N. (2009). Synthesis and single crystal structure analysis of three novel benzoylthiourea derivatives. Turkish Journal of Chemistry, 33(6), 857-868.
Keche, A. P., Hatnapure, G. D., Tale, R. H., Rodge, A. H., & Kamble, V. M. (2012). Synthesis, antiinflammatory
and antimicrobial evaluation of novel 1-acetyl-3, 5-diaryl-4, 5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties. Bioorganic & Medicinal Chemistry Letters, 22(21), 6611-6615.
Lee, J., Lee, J., Kim, J., Kim, S. Y., Chun, M. W., Cho, H., Hwang, S.W., Oh, U., Park, Y.H., Marquez, V. E., Beheshti, M., Szabo, T., Blumberg, P. M. (2001). N-(3-Acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl) thiourea derivatives as potent vanilloid receptor agonists and analgesics. Bioorganic & Medicinal Chemistry, 9(1), 19-32.
Lipowska, M., Hayes, B. L., Hansen, L., Taylor, A., & Marzilli, L. G. (1996). Rhenium (V) oxo complexes of novel N2S2 dithiourea (DTU) chelate ligands: Synthesis and structural characterization. Inorganic chemistry, 35(14), 4227-4231.
Mansuroglu, D. S., Arslan, H., Flörke, U., & Külcü, N. (2008). Synthesis and characterization of nickel and copper complexes with 2, 2-diphenyl-N-(alkyl (aryl) carbamothioyl) acetamide: The crystal structures of HL1 and cis-[Ni (L1) 2]. Journal of Coordination Chemistry, 61(19), 3134-3146.
Rahamathulla, R., Khairul, W. M., Salleh, H., Adli, H. K., Isa, M. I. N., & Tay, M. G. (2013). Synthesis, Characterization and Electrochemical Analysis of V-Shaped Disubstituted Thiourea-Chlorophyll Thin Film as Active Layer in Organic Solar Cells. Int. J. Electrochem. Sci, 8, 3333-3348.
Saeed, A., Erben, M. F., & Bolte, M. (2013). Synthesis, structural and vibrational properties of 1-(adamantane-
1-carbonyl)-3-halophenyl thioureas. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,
102, 408-413.
Tadjarodi, A., Adhami, F., Hanifehpour, Y., Yazdi, M., Moghaddamfard, Z., & Kickelbick, G. (2007).Structural characterization of a copper (II) complex containing oxidative cyclization of N-2-(4-picolyl)-N′-(4-methoxyphenyl) thiourea, new ligands of 4-picolylthiourea derivatives and the precursor molecular structure ofoxidative cyclization of N-(2-pyridyl)-N′-(4-methoxyphenyl) thiourea. Polyhedron, 26(15), 4609-4618.
Ugur, D., Arslan, H., & Külcü, N. (2006). Synthesis, characterization and thermal behavior of 1, 1-dialkyl-3-(4-(3, 3-dialkylthioureidocarbonyl)-benzoyl) thiourea and its Cu (II), Ni (II), and Co (II) complexes. Russian Journal of Coordination Chemistry, 32(9), 669-675.
Weiqun, Z., Kuisheng, L., Yong, Z., & Lu, L. (2003). Structural and spectral studies of N-(4-chloro) benzoyl-N′-2-tolylthiourea. Journal of Molecular Structure, 657(1), 215-223.
Ziegler‐Skylakakis, K., Nill, S., Pan, J. F., & Andrae, U. (1998). S‐oxygenation of thiourea results in the formation of genotoxic products. Environmental and Molecular Mutagenesis, 31(4), 362-373.
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Published
2016-06-10
How to Cite
M. Khairul, W., Suskri, S. A., Rahamathullah, R., & Ismail, N. (2016). Synthesis and Spectroscopic Studies of Alkyl Substituted Thiourea Derivatives Towards the Selected Antibacterial Activities. EDUCATUM Journal of Science, Mathematics and Technology, 3(1), 28–33. Retrieved from https://ojs.upsi.edu.my/index.php/EJSMT/article/view/42
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