Synthesis, Characterization and in Vitro Antimicrobial Studies of Schiff-Bases Derived from Acetylacetone and Amino Acids and their Oxovanadium(IV) Complexes
American Journal of Applied Chemistry
Volume 1, Issue 4, October 2013, Pages: 59-66
Received: Oct. 26, 2013; Published: Nov. 10, 2013
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Authors
Misbah ur Rehman, Institute of Chemical Science, Gomal University, D.I. Khan, KPK, Pakistan
Muhammad Imran, Institute of Chemical Science, Bahauddin Zakariya University, Multan, Pakistan
Muhammad Arif, Institute of Chemical Science, Bahauddin Zakariya University, Multan, Pakistan
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Abstract
A series of novel amino acid derived Schiff-bases and their Oxovanadium(IV) complexes were synthesized and well characterized by elemental analyses, spectral studies, conductivity and magnetic measurements. Physical and analytical data suggest that the Schiff bases act as tridentate ligands towards metal ion via azomethine-N, deprotonated-O of carboxylic group and enolic-O group of acetylacetone. All the complexes have lower molar conductance values, indicating their non-electrolytic nature. The synthesized ligands, along with their metal complexes were screened for their in-vitro antibacterial activity against two Gram-negative (Escherichia coli, Salmonella typhi) and two Gram-positive (Bacillus subtilis, Staphylococcus aureus) bacterial strains and for in vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, and Candida glaberata species. The results of these studies revealed that all the compounds and their metal complexes showed significant antibacterial and antifungal potency. Brine shrimp bioassay was also carried out for in vitro cytotoxic properties against Artemia salina.
Keywords
Schiff-bases, Amino Acid, Antibacterial, Antifungal, Cytotoxicity
To cite this article
Misbah ur Rehman, Muhammad Imran, Muhammad Arif, Synthesis, Characterization and in Vitro Antimicrobial Studies of Schiff-Bases Derived from Acetylacetone and Amino Acids and their Oxovanadium(IV) Complexes, American Journal of Applied Chemistry. Vol. 1, No. 4, 2013, pp. 59-66. doi: 10.11648/j.ajac.20130104.13
References
[1]
A. Elmali, M. Kabak, Y. Elerman, , "Keto-enol tautomerism, conformations and structure of N-(2-hydroxy-5- methylphenyl), 2-hydroxybenzaldehydeimine," J. Mol. Struct. 2000: 477(1-3): 151-158.
[2]
A. M. EI- Hendawy, E. G. EI-Kourashy, M. M. Shanab, "Schiff base complexes of ruthenium(III), molybdenum(VI) and uranium(VI), and use of the former as catalytic organic oxidants" Polyhedron. 1992: 11: 523-530.
[3]
A. L. Lehlinger, "Biochemistry", 2nd Ed. Worth Publisher, 1975: 563-564.
[4]
A. D. Garnovskii, A. L. Nivorozhkin, V. I. Minkin, "Ligand environment and the structure of schiff base adducts and tetracoordinated metal-chelates" Coord. Chem. Rev. 1993: 126(1-2): 1-69.
[5]
W. T. Anna, J. L. Eric, A. K. Michael, Lai, A. K. Tasneem, "Novel N-hydroxyguanidine derivatives as anticancer and antiviral agents". J. Med. Chem. 1984; 27 (2):236–238.
[6]
H. W. Pou, G. K.James, J. L. Eric, M. C. Michael, "Design, synthesis, testing, and quantitative structure-activity relationship analysis of substituted salicylaldehyde Schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus". J. Med. Chem. 1990: 33 (2): 608–614.
[7]
Z. Travnicek, M. Malon, Z. Sindelar, K. Dolezal, J. Rolcik, V. Krystof, M. Strnad, J. Marek, "Preparation, physicochemical properties and biological activity of copper(II) complexes with 6-(2-chlorobenzylamino)purine (HL1) or 6-(3-chlorobenzylamino)purine (HL2). The single-crystal X-ray structure of [Cu(H+L2)2Cl3]Cl•2H2O" J. Inorg. Biochem. 2001: 84(1-2): 23-32
[8]
S. Iffet, L. Elif, A. Seza, S. Nurşen, S. Nazmiye, "Antimicrobial activities of N-(2-hydroxy-1-naphthalidene)-amino acid(glycine, alanine, phenylalanine, histidine, tryptophane) Schiff bases and their manganese(III) complexes." Biometals. 2004: 17 (2):115-120.
[9]
F. T. G. Huadson, "Vanadium Toxicology and Biological Significance" Elsevier, New York, 1996.
[10]
Z. H. Chohan, M. Arif, M. A. Akhtar, C. T. Supuran, "Metal-Based Antibacterial and Antifungal Agents: Synthesis, Characterization, and In Vitro Biological Evaluation of Co(II), Cu(II), Ni(II), and Zn(II) Complexes With Amino Acid-Derived Compounds" Bioinorg. Chem. Appl. 2006; 2006: 83131: 1-3.
[11]
J. Selbin, "Oxovanadium(IV) complexes". Coord. Chem. Rev. 1966: 1 (3): 293–314.
[12]
M. D. John, M. Alan, R. T. Ian, "Characterization of the ground ionic state of the NS molecule using photoelectron spectroscopy". J. Chem. Soc., Faraday Trans. 2. 1977: 73:147-151.
[13]
L. C. Richard, A. F. Walker, "Thermodynamics of Coordination to an Unsolvated Position in Vanadyl Acetylacetonate". J. Am. Chem. Soc. 1965: 87 (10):2128–2133
[14]
Atta-ur-Rahman, M. I. Choudhary, W. J. Thomsen, "Bioassay techniques for drug development", Harwood Academic Publishers, The Netherlands, 2001, pp. 16.
[15]
Atta-ur-Rahman, M. I. Choudhary, W. J. Thomsen, "Bioassay techniques for drug development" Harwood Academic Publishers: The Netherlands, 2001, pp. 22.
[16]
B. N. Meyer, N. R. Ferrigni, J. E. Putnam, L. B. Jacobsen, D. E. Nichols, J. L. McLaughlin, "Brine shrimp: a convenient general bioassay for active plant constituents," Planta Medica 1982: 45 (1):31–34.
[17]
A. W. Bauer, W. M. Kirby, J. C. Sherris, M. Turck, "Antibiotic susceptibility testing by a standardized single disk method" Am J. Clin. Pathol. 1966: 45 (4): 493–496.
[18]
R. L. Carlin, "Transition Metal Chemistry" 2nd ed. New York, 1965.
[19]
L. J. Bellamy, "The Infrared Spectra of Complex Molecules", John Wiley & Sons: New York, 1971.
[20]
J. R. Ferrero, Low-Frequency Vibrations of Inorganic and Coordination Compound, JohnWiley & Sons: New York, 1971.
[21]
K. Nakamoto, "Infrared Spectra of Inorganic and Coordination Compounds", 2nd ed. Wiley Interscience: New York, 1970.
[22]
G. Singh, P. A. Singh, K. Singh, D. P. Singh, R. N. Handa, S. N. Dubey, "Synthesis and structural studies of some bivalent metal complexes with bidentate Schiff base ligands," Proceedings of National Academy of Sciences India 2002: 72 (A-2): 87–95.
[23]
W. W. Simmons, "The Sadtler Handbook of Proton NMR Spectra", Sadtler Research Laboratories: Philadelphia, 1978.
[24]
D. J. Pasto, "Organic Structure Determination", Prentice Hall, London, 1969.
[25]
G. G. Mohamed, Z. H. Abd El-Wahab, "Salisaldehyde-2-aminobenzimidazole schiff base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II)" J. Therm. Anal. Calorim. 2003: 73:347-359.
[26]
S. R. Aswale, P. R. Mandlik, S. S. Aswale, A. S. Aswar, "Synthesis and characterization of Cr(III), Mn(III), Fe(III), Ti(III),VO(IV), Th(IV), Zr(IV) and UO2(VI) polychelates derived from bis-bidentate salicylaldimine Schiff base" Indian J. Chem. 2003: 42A:322-326.
[27]
R. K. Agarwal, I. Chakraborti, "Synthesis and characterization of some oxocation (IV) coordination compounds of Schiff bases derived from 4-aminoantipyrine" Polish J. Chem. 1994: 68(8):1085-1091.
[28]
Z. H. Chohan, "Antibacterial copper(II) complexes of 1,1′-symmetric ferrocene-derived Schiff-base ligands: studies of the effect of anions on their antibacterial properties"Appl. Organomet. Chem. 2002: 16:17–20.
[29]
Z. H. Chohan, M. Arif, Z. Shafiq, M. Yaqub, C. T. Supuran, "In vitro antibacterial, antifungal & cytotoxic activity of some isonicotinoylhydrazide Schiff's bases and their cobalt (II), copper (II), nickel (II) and zinc (II) complexes"J. Enzyme Inhib. Med. Chem. 2006: 21: 95–103.
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