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Synthesis, Characterization and Biological Evaluation of Some Novel Hydrazide Schiff’s Bases and Their Metal Complexes
Corresponding Author(s) : Zahid Shafiq
Asian Journal of Chemistry,
Vol. 25 No. 5 (2013): Vol 25 Issue 5
Abstract
N'-(4-Hydroxy-3-methoxyphenyl)methylidene]formic hydrazide (L-1), N'-[-(4-hydroxy-3- methoxyphenyl)methylidene]-3'-hydroxynaphthalene-2'-carbohydrazide (L-2) N'-[-(5- methylfuran-2-yl)methylidene]-3'-hydroxynaphthalene-2'-carbohydrazide (L-3), N'-[-1''-(4- fluorophenyl)ethylidene]-3'-hydroxynaphthalene-2'-carbohydrazide (L-4) and N'-[(-1'-(4- chlorophenyl)ethylidene]formic hydrazide (L-5) were synthesized and tested for their antioxidant activity. All these newly synthesized Schiff’s bases were treated with Cu(II), Co(II) and Zn(II) chlorides to form their respective complexes. Antioxidant activity of the synthesized ligands (L-1, L-2, L-3, L-4 and L-5), their corresponding metal(II) complexes, salts of the metal used in the complex formation and Trolox (as standard antioxidant) was measured in terms of their ability to scavenge the DPPH free radical. Ligand (L-4) was found to be the best antioxidant among all the ligands. As regards the activity of metal(II) complexes, Zn-L-4 exhibited the best antioxidant activity.
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- U. Kuehn, S. Warzeska, H. Pritzkow and R. Kraemer, J. Am. Chem. Soc., 123, 6125 (2001).
- J.M. Price, Fed. Proc., 20, 223 (1961); K.D. Karlin and J. Zubieta, Biochemical and Inorganic Perspectives, Adenine Press Guilderland, New York, p. 457 (1983).
- A.G. Mauk, R.A. Scott and H.B. Gray, J. Am. Chem. Soc., 102, 4360 (1980).
- R.J. Williams, J.P. Spencer and C. Rice-Evans, Free Radic. Biol. Med., 36, 838 (2004).
- F. Virgili and M. Marino, Free Radic. Biol. Med., 45, 1205 (2008).
- Viswanath, A. Urooj and N.G. Malleshi, Food Chem., 114, 340 (2009).
- W. Brand-Williams, M.E. Cuvelier and C. Berset, Lebensm. Wiss. Technol., 28, 25 (1995).
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References
H. Sies, Am. J. Med., 91, 31S (1991).
H. Esterbauer, R.J. Schaur and H. Zollner, Free Radic. Biol. Med., 11, 81 (1991).
K. Uchida, Free Radic. Biol. Med., 28, 1685 (2000).
G. Leonarduzzi, M.C. Arkan, H. Basaga, E. Chiarpotto, A. Sevanian and G. Poli, Free Radic. Biol. Med., 28, 1370 (2000).
R. Stocker, Curr. Opin. Lipidol, 10, 589 (1999).
Y.P. Kitaev, B. I. Buzykin and T.V. Troepolskaya, Russ. Chem. Rev., 39, 441 (1970).
N.P. Buu-Hoi, N.D. Xuong, N.H. Ham, F. Binon and R. Royer, J. Chem. Soc., 1358 (1953).
M. Fabin and G. Palmer, Biochemistry, 40, 1867 (2001).
T.S. Ma and T.M. Tian,Antibiot. Chemother., 3, 491(1953); I. Pozdnyakova and P.W. Stafshede, Biochemistry, 40, 13728 (2001).
U. Kuehn, S. Warzeska, H. Pritzkow and R. Kraemer, J. Am. Chem. Soc., 123, 6125 (2001).
J.M. Price, Fed. Proc., 20, 223 (1961); K.D. Karlin and J. Zubieta, Biochemical and Inorganic Perspectives, Adenine Press Guilderland, New York, p. 457 (1983).
A.G. Mauk, R.A. Scott and H.B. Gray, J. Am. Chem. Soc., 102, 4360 (1980).
R.J. Williams, J.P. Spencer and C. Rice-Evans, Free Radic. Biol. Med., 36, 838 (2004).
F. Virgili and M. Marino, Free Radic. Biol. Med., 45, 1205 (2008).
Viswanath, A. Urooj and N.G. Malleshi, Food Chem., 114, 340 (2009).
W. Brand-Williams, M.E. Cuvelier and C. Berset, Lebensm. Wiss. Technol., 28, 25 (1995).
A.I. Vogel, A Textbook of Quantitative Inorganic Analysis, ELBS and Longman: London, edn. 3, p. 827 (1978).
K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience: New York, edn. 3, p. 448 (1978).
R.K. Agarwal, J. Indian Chem. Soc., 65, 448 (1988).
L.J. Bellamy, Infrared Spectra of Complex Molecules, John Wiley: New York, p. 380 (1975).
W.W. Simmons, The Sadler Handbook of Protons NMR Spectra, Sadler Research Laboratories Inc: Philadelphia, p. 80 (1978).
D.J. Pasto, Organic Structure Determination, Prentice Hall International: London, p. 451 (1969).