Synthesis, Characterization, and Theoretical Studies of the New Antibacterial Zn(II) Complexes from New Fluorescent Schiff Bases Prepared by imidazo[4',5':3,4]benzo[1,2-c]isoxazole

Document Type : Research Article

Authors

1 Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, Iran

2 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

Abstract

The novel fluorescentheterocyclic bidentate ligands have been synthesized by the high yields reaction of 8-(4-chlorophenyl)-3-Iso-butyl-3H-imidazo[4',5':3,4]benzo[1,2-c]isoxazol-5-amine with p-hydroxybenzaldehyde and p-chlorobenzaldehyde. The ligands reacted with Zn(II) ion to gained novel complexes. The optical properties of these structures were checked and the outcomes represented that they showed interesting photophysical properties. Optimized geometries and assignment of the IR bands and NMR chemical shifts of the new complexes were also computed by using Density Functional Theory (DFT) methods that were in good agreement with the experimental values, confirming the suitability of the optimized geometries for Zn(II) complexes. These new compounds have shown potent antibacterial properties and their antibacterial activity (MIC) against Gram-positive and Gram-negative bacterial species were also specific.

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[3] Neelakantan M., Rusalraj F., Dharmaraja J., Johnsonraja S., Jeyakumar T., Pillai M.S., Spectral Characterization, Cyclic Voltammetry, Morphology, Biological Activities and DNA Cleaving Studies of Amino Acid Schiff Base Metal (II) Complexes, Spectrochim. Acta A Mol. Biomol. Spectrosc., 71(4): 1599-1609 (2008).
[6] Yue S.-M., Xu H.-B., Ma J.-F., Su Z.-M., Kan Y.-H., Zhang H.-J., Design and Syntheses of Blue Luminescent Zinc(II) and Cadmium(II) Complexes with Bidentate or Tridentate Pyridyl-imidazole Ligands, Polyhedron, 25(3): 635-644 (2006).
[7] Hoogenraad T., Koevoet R., de Ruyter Korver E., Oral Zinc Sulphate as Long-Term Treatment in Wilson’s Disease (Hepatolenticular Degeneration), Eur. Neurol., 18(3): 205-211 (1979).
[8] Pinilla-Tenas J.J., Sparkman B.K., Shawki A., Illing A.C., Mitchell C.J., Zhao N., Liuzzi J.P., Cousins R.J., Knutson M.D., Mackenzie B., Zip14 is a Complex Broad-Scope Metal-Ion Transporter Whose Functional Properties Support Roles in the Cellular Uptake of Zinc and Nontransferrin-Bound Iron, Am. J. Physiol., Cell Physiol., 301(4): C862-C871 (2011).
[9] Szarfman A., Tonning J.M., Levine J.G., Doraiswamy P.M., Atypical Antipsychotics and Pituitary Tumors: A Pharmacovigilance Study, Pharmacotherapy, 26(6): 748-758 (2006).
[10] Deng B.-L., Zhao Y., Hartman T.L., Watson K., Buckheit R.W., Pannecouque C., De Clercq E., Cushman M., Synthesis of Alkenyldiarylmethanes (ADAMs) Containing Benzo [d] Isoxazole and Oxazolidin-2-one Rings, A New Series of Potent Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors, Eur. J. Med. Chem., 44(3): 1210-1214 (2009).
[11] Loudon J., Tennant G., Substituent Interactions in Ortho-Substituted Nitrobenzenes, Chem. Soc. Rev., 18(4): 389-413 (1964).
[12] Munsey M.S., Natale N.R., The Coordination Chemistry of Isoxazoles, Coord. Chem. Rev., 109(2): 251-281 (1991).
[14] Joux F., Lebaron P., Use of Fluorescent Probes to Assess Physiological Functions of Bacteriaat Single-Cell Level, Microbes Infect., 2(12): 1523-1535 (2000).
[15] Preston P.N., "The Chemistry of Heterocyclic Compounds, Benzimdazoles and Cogeneric Tricyclic Compounds", John Wiley & Sons, Inc., Vol. 40 (2009).
[16] Rahimizadeh M., Pordel M., Bakavoli M., Bakhtiarpoor Z., Orafaie A., Synthesis of Imidazo[4,5-a]acridones and Imidazo[4,5-a]acridines as Potential Antibacterial Agents, Monatsh. Chem., 140(6): 633-    (2009).
[19] Lee C., Yang W., Parr R.G., Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density, Phys. Rev. B, 37(2): 785- 789 (1988).
[20] Frisch M., Trucks G., Schlegel H., Scuseria G., Robb M., Cheeseman J., Montgomery Jr J., Vreven T., Kudin K., Burant J., Gaussian 03, Revision B. 03, Gaussian, Inc., Wallingford, CT, 2004. Gaussian 03, Revision B. 05, MJ Frisch, et al. Gaussian, Inc., Pittsburgh, PA:  (2003).
[22] Rezazadeh M., Pordel M., Davoodnia A., Saberi S., New Fluorescent 3H-imidazo [4, 5-e][2, 1] Benzoxazoles: Synthesis, Spectroscopic Characterization, and Antibacterial Activity, Chem. Heterocycl. Compd., 51(10): 918-922 (2015).
[23] Vosburgh W.C., Cooper G.R., Complex ions. I. The Identification of Complex Ions in Solution by Spectrophotometric Measurements, J. Am. Chem. Soc., 63(2): 437-442 (1941).
[24] Saureu S., de Graaf C., TD-DFT Study of the Light-Induced Spin Crossover of Fe(iii) Complexes, Phys. Chem. Chem. Phys. , 18(2): 1233-1244 (2016).
[26] Preti C., Tosi G., Massacesi M., Ponticelli G., Chromium (III) Halide Complexes with Isoxazole and Substituted Isoxazoles as Ligands, Spectrochim. Acta A Mol. Biomol. Spectrosc., 32(12): 1779-1784 (1976).
[28] Pordel M., Abdollahi A., Razavi B., Synthesis and Biological Evaluation of Novel Isoxazolo[4,3-e]indoles as Antibacterial Agents, Russ. J. Bioorg. Chem., 39(2): 211-214 (2013).
[29] Tweedy B., Plant Extracts with Metal Ions as Potential Antimicrobial Agents, Phytopathology, 55: 910-914 (1964).