SYNTHESES AND EVALUATION OF THE ANTIMICROBIAL ACTIVITIES OF HALOGENATED IMIDAZOLES AND THEIR MN(II), NI(II), AND ZN(II) COMPLEXES
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Abstract
4, 5-Dichloroimidazole (4, 5-DCI) and 2, 4,5-Tribromoimidazole were synthesized, recrystallized from the appropriate solvents and characterized using spectroscopic methods. They were screened for their antimicrobial activities against five bacterial strains namely: Escherichia coli, Bacillus cereus strain CF7, Bacillus thuringensis strain EB151, Pseudomonas aeruginosa strain 335K55, and Pseudomonas aeruginosa strain PG1. These microorganisms were very sensitive to the compounds. Their sensitivities were increased appreciably by the Ni2+ and Mn2+ complexes of 4, 5-dichloroimidazole and reduced by its Zn2+ complex. Their sensitivities towards 2, 4, 5-tribromoimdazole were either greatly reduced or totally lost upon complexation. The differences in these sensitivities are attributed majorly to the halogens as the metal ions are common to both ligands.
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References
. Jain, A.K., Ravichandran, V., Sisodiya, M. and Agrawal, R.K. (2010). Synthesis and antibacterial evaluation of 2-substituted-4,5diphenyl-N-alkyl imidazole derivatives. Asian Pac J Trop Me, 471, 4
. Sharma V. and Khan, M.S. (2001). Synthesis of novel tetrahydroimidazole derivatives and studies for their biological properties. European Journal of Medicinal Chemistry, 36, 651-658
. Zampieri, D., Mamolo, M.G., Laurini, E., Scialino, G., Banfi, E. and Vio, L. (2008). Antifungal and antimycobacterial activity of 1-(3, 5diaryl-4, 5-dihydro-1H-pyrazol-4-yl) 1H-imidazole derivatives. Bioorganic and Medicinal Chemistry, 16(8), 4516–4522.
. Sharma, D., Narasimhan, B., Kumar, P., Judge, V., Narang, R. and DeClereq, E. (2009). Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. European Journal of Medicinal Chemistry, 44, 2347-2353
. Duru, I.A., Ngochindo, R.I., and Duru, C.E. (2014). Enhancement of the bioactivity of 4,5dibromoimidazole by its Co (II) complex. International Organization of Scientific Research Journal Of Applied Chemistry 7(9), 28– 32
. Khabnadideh, S., Rezaei, A.A., Khalafi-Nezad, A., Bahrinajafi, R., Mohamadi, R. And Farrokhroz, A.A. (2003). Synthesis of N-alkylated derivatives of imidazoles as antifungal agents. Bioorganic and Medicinal Chemistry Letter, 13, 2863-2865
. Sunderland, M.R., Cruikshank, R.H. and Leighs, S.J. (2014). The efficacy of antifungal azole and antiprotozoal compounds in the protection of wool from keratin-digesting insect larvae. Textile Research Journal, 84(9): 924-931
. Ogata, M and Matsumoto, H. (1987). Synthesis and antifungal activity of new 1-vinylimidazoles. Journal of Medicinal Chemistry, 30, 1348-1354.
. Zhan, P., Liu, X., Zhu, J., Fang, Z., Li, Z., Pannecouque C. and Clercq, E.D. (2009). Synthesis and biological evaluation of imidazole thioacetanilides as novel nonnucleoside HIV-1 reverse transcriptase inhibitors. Bioorganic and Medicinal Chemistry, 17(16), 5775–5781.
. Alkahtani, H.M., Abbas, A.Y., and Wang, S. (2012). Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents. Bioorganic and Medicinal Chemistry Letter, 22(3), 1317–1321.
. Baroniya, S., Anwer, Z., Sharma, P.K., Dudhe, R., and Kumar, N. (2010). Recent advancement in imidazole as anticancer agents. A review. Der Pharmacia Sinica, 1(3), 172-182.
. Wang, X., Liu, L. and Li, Y. et al. (2013). Design, synthesis and biological evaluation of novel hybrid compounds of imidazole scaffoldbased 2-benzylbenzofuran as potent anticancer agents. European Journal of Medicinal Chemistry, 62, 111–121.
. Ucucu, U., Karanburun, N.G and Isikdag, I. (2001). Synthesis and analgesic activity of some i-benzyl-2substituted-4,5-diphenyl-1HImidazole derivatives. Il Farmaco, 56, 285-290
. Kankala, S., Kankala, R.K., Prasad, G., Thota, ., Nerella, S., Gangula, M.R., Guguloth, H., Kagga, M., Vadde, R. and Vasam, C.S. (2013). Regioselective synthesis of isoxazolemercaptobenzimidazole hydride and their in vivo analgesic and antiinflammatory activity studies. European Journal of Medicinal Chemistry, 45, 2245-2249
. Steel, H.C., Tintinger, G.R. and Anderson, R. (2008). Comparison of the anti-inflammatory activities of imidazole antimycotics in relation to molecular structure. Chemical Biology Drug Design, 72(3), 225-228
. Iqbal, M.S., Ahmad, A.R., Sabir, M., and Asad, S.M. (1999). Preparation, characterization and biological evaluation of copper (II) and zinc (II) complexes with cephalexin. Journal of Pharmacy and Pharmacology, 51(4), 371-375
. Revanasiddappa, H.D., Shivakumar, L., Prasad, K.S. Vijay, B., and Jayalakshmi, B. (2012). Synthesis, Structural Characterization and Antimicrobial Activity Evaluation of Manganese (II) Complexes with Biologically Important Drugs.
. Chemical Sciences Journal, 3, 64-73 18. Lutz, A.W. and Delorenzo, S. (1967). Novel halogenated imidazoles, Chloroimidazoles. Journal of heterocyclic chemistry, 4(3): 400-401.
. Stensio, D.A., Wahlberg, K. and Wharen, R. (1973). Synthesis of brominated imidazoles, Acta Chemica Scandinavica, 27: 2179-2183.
. Cowan, S.T. and Steel, K.J. (1965). Manual of Identification of Medical Bacteria. Cambridge University Press, New York. 1-40.
. Ogueke, C.C., Jude, N., Okoli, I.C., and Anyanwu, B.N. (2007). Antibacterial activities and toxicological potentials of crude ethanolic extracts of Euphorbia hirta, Journal of American Science, 3(3):11- 16
. Akujobi, C., Anyanwu, B.N., Onyeze, C. and Ibekwe, V.I. (2004). Antibacterial Activities and Preliminary Phytochemical Screening of Four Medicinal Plants. Journal of Applied Sciences, 7(3): 4328 – 4338.
. Esimone, C.O., Adiukwu, M.U. and Okonta, J.M. (1998). Preliminary Antimicrobial Screening of the Ethanolic Extract from the Lichen Usnea subfloridans (L). Journal of Pharmaceutical Research and Development, 3(2): 99-102