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Synthesis, Characterization and Antimicrobial Potential of Novel Conjugated Schiff Bases
Corresponding Author(s) : Muhammad Yousaf
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
Anthracenylamine and naphthylamine were reacted with 1, 3-cyclohexadienone and 1, 4- benzoquinone in order to prepare four (1, 2, 3 & 4) conjugated Schiff bases for the evaluation of their antibacterial as well as antifungal activities. The results of their activities were compared with standard drugs against three strains of bacteria as well as three strains of fungi and they showed that the Schiff base 4 (C34H22N2O) exhibited good inhibition zones against all the strains of bacteria (10.74 ± 0.65, 10 ± 0.675, 10.65 ± 0.75 mm) as well as fungi (9.15 ± 0.815, 10.25 ± 0.55, 10.5 ± 0.575 mm) as compared to others (1, 2 & 3). The Schiff base 3 (C26H24N4) showed better potential for S. aureus (10 ± 0.856 mm) strain of bacteria and A. alternate (10.5 ± 2.150 mm) strain of fungi. Its activity against other two strains of bacteria and fungi was also better than other two Schiff bases (1 & 2). The Schiff base 2 (C26H22N2) exhibited reasonable activity against B. subtilus (10 ± 0.715 mm) and A. alternate (8.55 ± 0.015 mm). The compound (1) showed least antibacterial (4.5 ± 0.815, 5 ± 0.716, 4.75 ± 0.950 mm) as well as antifungal (4 ± 0.575, 4.15 ± 0.570, 6.5 ± 1.725 mm) activity. From the results it is concluded that delocalization of p electrons has the positive influence on the antimicrobial potential of the titled Schiff bases. Thus these Schiff bases may serve as a basis for the chemical modifications directed towards the development of a new class of antibacterial agents.
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References
T.D. Chaudhari and S.S. Subnis, Bull. Haffkine, 4, 85 (1986).
S. Shah, R. Vyas and R.H. Mehta, J. Indian Chem. Soc., 69, 590 (1992).
K. Sahu, R.K. Behera, R.C. Pathaik, A. Nayak and G.B. Behera, Indian J. Chem., 18B, 557 (1979).
M. Abdul-Gawad, Y.M. Issa and S.M. Abd-Alhamid, Egypt. J. Pharm. Sci., 34, 219 (1993).
S.A. Khan, A.A. Siddiqui and S. Bhatt, Asian J. Chem., 14, 117 (2002).
A. Elmali, M. Kabak and Y. Elerman, J. Mol. Struct., 477, 151 (2000).
S.N. Pandeya, D. Sriram, G. Nath and E. Declercq, Eur. J. Pharm., 9, 25 (1999); doi:10.1016/S0928-0987(99)00038-X.
R. Mladenova, M. Ignatova, N. Manolova, T. Petrova and I. Rashkov, Eur. Polym. J., 38, 989 (2002); doi:10.1016/S0014-3057(01)00260-9.
P. Singh, R.L. Goel and B.P. Singh, J. Indian Chem. Soc., 52, 958 (1975).
D. Singh, K. Kumar, S.S. Dhiman and J. Sharma, J. Enzyme Inhib. Med. Chem., 25, 21 (2010); doi:10.3109/14756360902932750.
A.D. Logu, V. Onnis, B. Saddi, C. Congiu, M.L. Schivo and M.C. Cocco, J. Antimicrob. Chemother., 49, 275 (2002); doi:10.1093/jac/49.2.275.
M. Cuenca-Estrella, B. Ruiz-Diez, J.V. Martinez-Suarez, A. Monzon and J.L. Rodriguez-Tudela, J. Antimicrob. Chemother., 43, 149 (1999); doi:10.1093/jac/43.1.149.
M. Akbar, F. Naser and K. Mehdi, Turk. J. Chem., 34, 367 (2010).
A.A. Al-meiry, Y.K. Al-majedy, H.A. Ibrahim and A.A. Al-tamimi, Org. Med. J., 2, 4 (2012).
M.R. Karekal, V. Biradar and M. Bennikallu Hire Mathada, Bioinorg. Chem. Appl., Article ID 315972, (2013); doi:10.1155/2013/315972.
X. Xiao, W. Jiag-Thao and B. Jie, J. Chem. Eng .Chinese Univ., 4, 160 (2010).
J. Sunny, J. Anil, G. Avneet and Hemraj, Asian J. Pharm. Clin. Res., 5,199,(2012).