Synthesis, Molecular Structure and Antibacterial Activity of Benzylmethyl-4-Methyl-3-Thiosemicarbazone
Keywords:
Benzylmethyl-4-Methyl-3-Thiosemicarbazone, Antibacterial Activity, Crystal StructureAbstract
A novel Schiff base, benzylmethyl-4-methyl-3-thiosemicarbazone (BMM) derived from benzylmethylketone and 4-methylthiosemicarbazide was synthesized and characterized by elemental analysis, spectroscopic methods (IR, 1H NMR, 13C NMR) and physical means. The single crystal structure analysis of the Schiff base reveals that it crystallizes in a monoclinic system in the P21/c space group. BMM revealed moderate antibacterial activity on three bacterial strains with diameter zone of inhibition of 16 mm (E. coli), 14 mm (K. pneumonia ) and 13 mm (S. epidermidis ) compared with the standard drug, ciprofloxacin.
References
- Gionani, S.D., Varriale, A., Marzullo, V.M., Ruggiero, G., Staiano, M., Secchi, A., Pierno, L., Fiorello, A.M. and D’Auria, S. (2012) Determination of Benzylmethylketone? A Commonly Used Precursor in Amphetamine Manufacture. Analytical Methods, 4, 3558-3564. https://doi.org/10.1039/c2ay25772f
- Parul, N., Subhangkar, N. and Mahato, A. (2012) Antimicrobial Activity of Different Thiosemicarbazone Compounds against Microbial Pathogens. International Research Journal of Pharmacy, 3, 350-363.
- Abou-Mehla, K.S. and Faruk, H. (2008) Bimetallic Complexes of Schiff Base Bis-4-hydroxycoumarin-3-yl]-1N,5N-thiocarbohydrazone as a Potentially Dibasic Pentadentate Ligand. Synthesis, Spectral and Antimicrobial Properties. Journal of the Iranian Chemical Society , 5, 122-134. https://doi.org/10.1007/BF03245825
- Patil, S.A., Naik, V.H., Kulkarni, A.D. and Badami, P.S. (2010) DNA Cleavage, Antimicrobial, Spectroscopic and Fluorescence Studies of Co(II), Ni(II) and Cu(II) Complexes with SNO Donor Coumarin Schiff Bases. Spectrochimica Acta A, 75, 347-354. https://doi.org/10.1016/j.saa.2009.10.039
- Teytz, Y., Ronen, D., Vansover, A., Stematsky, T. and Riggs, J.L. (1994) Inhibition of Human Immunodeficiency Virus by N-methylisatin-beta 4':4'-Diethylthiosemicarbazoneand N-Allylisatin-beta4':4'-diallythiosemicarbazone. Antiviral Research , 24, 305-314. https://doi.org/10.1016/0166-3542(94)90077-9
- Teytz, Y., Barko, N., Abramoff, M. and Ronen, D. (1994) Relationships between Structure and Antiretroviral Activity of Thiosemicarbazone Derivatives. Chemotherapy, 40, 195-200. https://doi.org/10.1159/000239192
- Hall, I.H., Wong, O.T. and Chapman, J.M. (1995) Cytotoxicity of Imides-N-alkyl Semicarbazones, Thiosemicarbazones, Acetyl Hydrazones and Related Derivatives. Anticancer Drugs, 6, 147-153. https://doi.org/10.1097/00001813-199502000-00017
- Tahmeena, K., Rumana, A., Seema, J. and Khan, A.R. (2015) Anticancer Potential of Metal Thiosemicarbazone Complexes: A Review. Der Chemica Sinica, 6, 1-11.
- Liu, M., Lin, T. and Sartorelli, A.C. (1992) Synthesis and Antitumor Activity of Amino Derivatives of Pyridine-2-Carboxaldehyde Thiosemicarbazone. Journal of Medicinal Chemistry , 35, 3672-3677. https://doi.org/10.1021/jm00098a012
- Mignot, A., Miocque, M., Binet, P., Rapin, J.R., Rinjard, P., Roux, M., Cals, M.J. and Ekindjian, J.C. (1980) Thiosemicarbazones d'aldehydes Aromatiques Antiinflammatoires: Pharmacologie, etude pharmacocinetique preliminaire, action sur le fibroblaste en culture. European Journal of Medicinal Chemistry, 15, 33-40.
- Bemstein, J., Yale, H.L., Losee, K., Holsing, M., Martins, J. and Lott, W.A. (1951) The Chemotherapy of Experimental Tuberculosis. III. The Synthesis of Thiosemicarbazones and Related Compounds. Journal of the American Chemical Society , 73, 906-912. https://doi.org/10.1021/ja01147a007
- Nfor, E.N., Esemu, S.N., Ayimele, G.A., Ededet, A.E., Iniama, G.E. and Offiong, E.O. (2011) Copper (II) and Nickel (II) Complexes of 4-Phenylsemicarbazones: Synthesis, Stereochemistry and Antimicrobial Activity. Bulletin of the Chemical Society of Ethiopia, 25, 361-370. https://doi.org/10.4314/bcse.v25i3.68668
- Majoumo-Mbe, F., Nde, D.T., Mukoko, I.N., Offiong, E.O. and Nfor, E.N. (2016) Synthesis, Crystal and Molecular Structure of Manganese (II) Complex of 2-Acetylpyridine N(4) Ethylthiosemicarbazone. Communications in Inorganic Synthesis , 4, 5-11.
- Nfor, E.N., Ahmad, H., Majoumo-Mbe, F., Njah, I.N., Offiong, E.O. and Bourne, S. (2013) Synthesis, Crystal Structure and Antifungal Activity of a Ni(II) Complex of a New Hydrazone Derived from Antihypertensive Drug Hydralazine Hydrochloride. Polyhedron, 63, 207-213. https://doi.org/10.1016/j.poly.2013.07.028
- Bauer, A.W., Kirby, W.M., Sherris, C. and Turck, M. (1966) Antibiotic Susceptibility Testing by a Standardized Single Disc Method. American Journal of Clinical Pathology, 45, 493-499.
- El-Sherif, A.A., Shoukry, M.M. and Abobakr, L.O. (2013) Bivalent Transition Metal Complexes of Cetirizines: Spectroscopic, Equilibrium Studies and Biological Activity. Spectrochimica Acta (A), 112, 290-300.
- El-Sherif, A.A. and Shoukry, M.M. (2007) Ternary Copper(II) Complexes Involving 2-(aminomethyl)-benzimidazole and Some Bio-Relevant Ligands. Equilibrium Studies and Kinetics of Hydrolysis for Glycine Methyl Ester under Complex Formation. Inorganica Chimica Acta , 360, 473-487.
Downloads
Published
Issue
Section
License
Copyright (c) IJSRST

This work is licensed under a Creative Commons Attribution 4.0 International License.