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Syntheses, Characterization and Antimicrobial Screening of N-(Benzothiazol-2-yl)-2,5-Dichlorobenzenesulphonamide and Its Cu(I), Ni(II), Mn(II), Co(III) and Zn(II) Complexes
Corresponding Author(s) : L.N. Obasi
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
N-(Benzothiazol-2-yl)-2,5-dichlorobenzenesulphonamide (DCBS2ABT) was synthesized by the condensation (by refluxing) of 2-aminobenzothiazole and 2,5-dichlorobenzenesulphonylchloride in acetone at 230 ºC. The resulting crude precipitates were recrystallized in absolute ethanol. Five metal complexes of copper(I), nickel(II), manganese(II), cobalt(III) and zinc(II) of the ligand were synthesized. The compounds were characterized using magnetic susceptibility measurements, UV/visible spectrophotometry, elemental microanalysis, infrared, 1H and 13C NMR spectroscopies. The antimicrobial tests of the ligands and its metal complexes were carried out on both multi-resistant bacterial strains isolated under clinical conditions and cultured species using agar-well diffusion method. The multi-resistant bacterial strains used were Escherichia coli, Proteus species, Pseudomonas aeroginosa and Staphylococcus aureus were isolated from dogs. The culture species were Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 25922) Staphylococcus aureus (ATCC 25923) and the fungi, Candida krusei (ATCC 6258) and Candida albicans (ATCC 90028). The tests were performed both in vitro and in vivo. Thus the inhibition zone diameter, the minimum inhibitory concentration and the lethal and effective concentrations (LC50 and EC50) were determined. The antimicrobial activities of the compounds were compared with those of ciprofloxacin and trimethoprim-sulphamethoxazole as antibacterial agents and fluconazole as an antifungal drug. All the compounds showed varying activities against the cultured typed bacteria and fungi used. However, they were less active than the standard drugs used except fluconazole, which did not show any activity against Candida krusei (ATCC 6258) but the ligand, DCBS2ABT and all the metal complexes synthesized were very active against it. The lethal concentration (LC50) ranged from 81.00 ± 6.8-256.30 ± 36.7 ppm. These are within the permissible concentrations.
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- S.N. Banerjee and T.G. Emori, Am. J. Med., 91 (suppl.3B), 86S (1991).
- C.M. Beck-Sauge and T.R. Jarvis, J. Infect. Dis., 167, 1247 (1991).
- J.D. Edward, M.N. Hughes and K.J. Rutt, J. Chem. Soc. (A), 2101-2105 (1969).
- M. Tsuruoka and I. Seikutsugaka, Med. Biol., 10, 296 (1947).
- R.P. Kapoor, M.K. Rastogi, R. Khanna and C.P. Garg, Indian J. Chem., 23B, 390 (1984).
- A. Garcia-Raso, J.J. Fiol, G. Martorell, A. Lopez-Zafra and M. Quiros, Polyhedron, 6, 613 (1997).
- M.R. Chaurasia, P. Shukla and N.K. Singh, Def. Sci. J., 2, 75 (1982).
- N.L. Obasi, P.O. Ukoha and K.F. Chah, J. Chem. Soc. (Nigeria), 35, 190 (2010).
- N.L. Obasi, P.O. Ukoha, K.F. Chah and A.O. Anaga, Asian J. Chem.,23, 2043 (2011).
- M.J. Sprague and L.W. Kissinger, J. Am. Chem. Soc., 63, 578 (1941).
- K.F. Chah, C.A. Eze, C.E. Emuelosi and C.O. Esimone, J. Ethnopharm., 104, 164 (2006).
- O.O. Ojo, A.O. Ajayi and I.I. Anibjuwon, J. Zhejiang Univ. Sci., 8, 189 (2007).
- J.L. McLaughlin, C.J. Chang and D. Smith, Bench-top bioassays for the discovery of bioactive natural products: An update. In ed: Atta-urRahman, Studies in Natural Product Chemistry, vol. 9, Amsterdam, Elsevier Sci. Publ. BV, pp. 383-408 (1991).
- A. Giusti and G. Peyronel, Spectrochim. Acta A, 38, 975 (1982).
- Z.M. Zaki, S.S. Hagga and A.A. Soayed, Spectrosc. Lett., 31, 757 (1998).
- F.A. Cotton, G. Wilkinson, C.A. Murillo and M. Bochmann, Advanced Inorganic Chemistry, 6th ed. John Wiley and Sons, New York, pp. 758-876 (1999).
- S. Sweetman, in ed.: Martindale, The Complete Drug Reference, Pharmaceutical Press, London; ISBN 0-85369-550-4, edn 34 (2004).
References
S.N. Banerjee and T.G. Emori, Am. J. Med., 91 (suppl.3B), 86S (1991).
C.M. Beck-Sauge and T.R. Jarvis, J. Infect. Dis., 167, 1247 (1991).
J.D. Edward, M.N. Hughes and K.J. Rutt, J. Chem. Soc. (A), 2101-2105 (1969).
M. Tsuruoka and I. Seikutsugaka, Med. Biol., 10, 296 (1947).
R.P. Kapoor, M.K. Rastogi, R. Khanna and C.P. Garg, Indian J. Chem., 23B, 390 (1984).
A. Garcia-Raso, J.J. Fiol, G. Martorell, A. Lopez-Zafra and M. Quiros, Polyhedron, 6, 613 (1997).
M.R. Chaurasia, P. Shukla and N.K. Singh, Def. Sci. J., 2, 75 (1982).
N.L. Obasi, P.O. Ukoha and K.F. Chah, J. Chem. Soc. (Nigeria), 35, 190 (2010).
N.L. Obasi, P.O. Ukoha, K.F. Chah and A.O. Anaga, Asian J. Chem.,23, 2043 (2011).
M.J. Sprague and L.W. Kissinger, J. Am. Chem. Soc., 63, 578 (1941).
K.F. Chah, C.A. Eze, C.E. Emuelosi and C.O. Esimone, J. Ethnopharm., 104, 164 (2006).
O.O. Ojo, A.O. Ajayi and I.I. Anibjuwon, J. Zhejiang Univ. Sci., 8, 189 (2007).
J.L. McLaughlin, C.J. Chang and D. Smith, Bench-top bioassays for the discovery of bioactive natural products: An update. In ed: Atta-urRahman, Studies in Natural Product Chemistry, vol. 9, Amsterdam, Elsevier Sci. Publ. BV, pp. 383-408 (1991).
A. Giusti and G. Peyronel, Spectrochim. Acta A, 38, 975 (1982).
Z.M. Zaki, S.S. Hagga and A.A. Soayed, Spectrosc. Lett., 31, 757 (1998).
F.A. Cotton, G. Wilkinson, C.A. Murillo and M. Bochmann, Advanced Inorganic Chemistry, 6th ed. John Wiley and Sons, New York, pp. 758-876 (1999).
S. Sweetman, in ed.: Martindale, The Complete Drug Reference, Pharmaceutical Press, London; ISBN 0-85369-550-4, edn 34 (2004).