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Research Article | Open Access

Preparation and Biological Activities of New Heterocyclic Azo Ligand and Some of Its Chelate Complexes

Siham Sami Al-Muhanaa( ), Abbas Hmood Al-Khafagy
Department of Chemistry, Faculty of Education for Women, University of Kufa, 54001 Najaf, Iraq
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Abstract

New azo ligand, 2[(Aminoantipyren) azo]-4, 5-bis(4-Methoxyphenyl)-H imidazole, (AAMPI) was prepared through coupling reaction of 4-amino antipyrine with 4, 5-bis (4-methoxyphenyl) imidazole. Then, complexation of ligand with ions Co(Ⅱ), Ni(Ⅱ), Cu(Ⅱ), Zn(Ⅱ), Cd(Ⅱ) and Hg(Ⅱ) were prepared to yield six complexes. The optimal conditions were studied for all complexes in the mole ratio between metal: ligand (M: L) as of 1:2 in the general formula [M(L)2]Cl2·H2O. Present results found the azo ligand was tridentate. The structures of ligand with complexes were identified by ultraviolet-visible spectroscopy (UV-Vis), Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1HNMR), carbon-13 nuclear magnetic resonance (13CNMR), mass spectrometry, elemental analysis (CHN), magnetic susceptibility and molar conductance. All the complexes exhibit octahedral geometry around the metal center. The antibacterial activities of synthesized compound were tested against the gram-negative, gram-positive bacteria and fungus. The results showed that the metal complexes exhibited antibacterial and antifungal activities compared with free ligand.

Keywords

Biological activityAzo ligandImidazoleMetal complexesCoupling reaction

References

[1]

M. Sheikhi, S. Shahab, and L. Filippovich, New derivatives of (E, E)-azomethines: Design, quantum chemical modeling, spectroscopic (FT-IR, UV/Vis, polarization) studies, synthesis and their applications: Experimental and theoretical investigations. Journal of Molecular Structure, 2018, 1152: 368-385.
Crossref Google Scholar
[2]

H. Chen, J. Motuzas, J.C. Diniz da Costa, et al., Degradation of azo dye Orange Ⅱ under dark ambient conditions by calcium strontium copper perovskite. Applied Catalysis B: Environmental, 2018, 221: 691-700.
Crossref Google Scholar
[3]

A. Gilewska, J. Masternak, K. Kazimierczuk, et al., Synthesis, structure, DNA binding and anticancer activity of mixed ligand ruthenium (Ⅱ) complex. Journal of Molecular Structure, 2018, 1155: 288-296.
Crossref Google Scholar
[4]

S.S. Kumar, S. Biju, and V. Sadasivan, Synthesis, structure characterization and biological studies on a new aromatic hydrazone, 5-(2-(1, 5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-yl) hydrazono)-2, 2-dimethyl-1, 3-dioxane-4, 6-dione, and its transition metal complexes. Journal of Molecular Structure, 2018, 1156: 201-209.
Crossref Google Scholar
[5]

H. Tabor, Metabolic studies on histidine, histamine, and related midazoles. Pharmacological Reviews, 1954, 6(3): 299-343.
Google Scholar
[6]

R. Kenchappa, Y.D. Bodke, and S. Telkar, Antifungal and anthelmintic activity of novel benzofuran derivatives containing thiazolo benzimidazole nucleus: An in vitro evaluation. Journal of Chemical Biology, 2017, 10(1): 11-23.
Crossref Google Scholar
[7]

M.V. Papadopoulou, W.D. Bloomer, and H.S. Rosenzweig, The antitubercular activity of various nitro (triazole/imidazole)-based compounds. Bioorganic & Medicinal Chemistry, 2017, 25(21): 6039-6048.
Crossref Google Scholar
[8]

R.T. Iminov, A.V. Tverdokhlebov, A.A. Tolmachev, et al., Simple and convenient synthesis of 2, 3, 4, 5-tetrahydro-1, 5-dioxopyrrolo[1, 2-a] quinazoline-3a (1H)-carboxylic acids in multi-gram scale. Heterocycles, 2008, 75(7): 1673-1680.
Crossref Google Scholar
[9]

N. Liu, D. Ding, L. Wang, et al., Two novel Mg(Ⅱ)-based and Zn (Ⅱ)-based complexes: inhibiting growth of human liver cancer cells. Brazilian Journal of Medical and Biological Research, 2018, 51(2).
Crossref Google Scholar
[10]

K. Karrouchi, S. Radi, and Y. Ramli, Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review. Molecules, 2018, 23(1): 134.
Crossref Google Scholar
[11]

P. Palanisamy, S.J. Jenniefer, and P.T. Muthiah, Synthesis, characterization, antimicrobial, anticancer, and antituberculosis activity of some new pyrazole, isoxazole, pyrimidine and benzodiazepine derivatives containing thiochromeno and benzothiepino moieties. RSC Advances, 2013, 3(42): 19300-19310.
Crossref Google Scholar
[12]

M.A. Metwally, Y.A. Suleiman, M.A. Gouda, et al., Synthesis, antitumor and antioxidant evaluation of some new antipyrine based azo dyes incorporating pyrazolone moiety. Int. J. Mod. Org. Chem, 2012, 1(3): 213-225.
Google Scholar
[13]

J.R.E. Hoover, A.R. Day, Preparation of some imidazole derivatives of 1, 4-naphthoquinone. Journal of the American Chemical Society, 1954, 76(16): 4148-4152.
Crossref Google Scholar
[14]

S. Shibata, M. Furukawa, and R. Nakashima, Syntheses of azo dyes containing 4, 5-diphenylimidazole and their evaluation as analytical reagents. Analytica Chimica Acta, 1976, 81(1): 131-141.
Crossref Google Scholar
[15]
H. Huheey, E.A. Keiter, and R.L. Keiter, Inorganic chemistry: principles of structure and reactivity, 4th ed. Harper Collin College Publishers, 1993.
[16]

N. Raman., J.D. Raja, Synthesis, structural, characterization and antibacterial studies of some bio sensitive mixed ligand copper (Ⅱ) complexes. Indian J. Chem. , 2007, 46A: 1611-1614.
Google Scholar
[17]

A.S. Al-Rammahi, A.H. Al-khafagy, and F.A. Al-Rammahi, Synthesis and characterization of oxazepen and imidazolin derivatives from 2-amino -5- mercapto 1, 3, 4-thiadiazol and studing of their biological activity. World J. pharm. Res. , 2015, 4(2): 1668-1680.
Google Scholar
[18]

A.H. Al-Khafagy, Synthesis, characterization and biological study of some new metal-azo chelate complexes. J. Chem. Pharm. Res. , 2016, 8(8): 296-302.
Google Scholar
[19]

A. Saeyda, Synthesis and characterization of some metal complexes derived from azo compound of 4, 4'-methylenedianiline and antipyrine: evaluation of their biological activity on some land snail species. Journal of Molecular Structure, 2015, 1099: 567-578.
Crossref Google Scholar
[20]

S. Suhad, Synthesis and spectral studies of heterocyclic azo dye complexes with Y (Ⅲ) and La (Ⅲ) ions. Al-Qadisiyah Journal of Pure Science, 2017, 19(1): 67-77.
Google Scholar
[21]

T. Giuseppe, Ligating properties of thionitrosoamines: I. neutral mononuclear N-thionitrosodimethylamine-palladium (Ⅱ) and-platinum (Ⅱ) complexes. Journal of Organometallic Chemistry, 1983, 252(3): 381-387.
Crossref Google Scholar
[22]

C. Gyana, Cobalt (Ⅱ) complexes of ONO donor Schiff bases and N, N donor ligands: synthesis, characterization, antimicrobial and DNA binding study. International Journal of Research in Chemistry and Environment, 2013, 32: 172-180.
Google Scholar
[23]

P.A.L. Sanjib, Synthesis, spectral and electrochemical properties of 1-alkyl-2-(naphthyl-β-azo) imidazole complexes of platinum (Ⅱ) and the reaction with pyridine bases. Single-crystal X-ray structure of dichloro-[1-ethyl-2-(naphthyl-β-azo) imidazole] platinum (Ⅱ). Polyhedron, 2000, 19(10): 1263-1270.
Crossref Google Scholar
[24]

S. Ayşe, Studies on mononuclear transition metal chelates derived from a novel (E, E)-dioxime: synthesis, characterization and biological activity. Journal of Coordination Chemistry, 2007, 60(6): 655-665.
Crossref Google Scholar
[25]
K. Nakamoto, Infrared and Raman spectra of inorganic and coordination compounds, 6rd ed. A John Wiley & Sons, Inc., 2009: 1-29, 57-62, 67, 313.
[26]

G. Valarmathy, R. Subbalakshmi, Synthesis, spectral characterization of biologically active novel Schiff base complexes derived from 2-sulphanilamidopyrimidine. Int. J Pharma Bio Sci, 2013, 4(2): 1019-1029.
Google Scholar
[27]

S. Pal, C. Sinha, Studies on the reactivity of cis-RuCl2 fragment in Ru (PPh3)2 (TaiMe) Cl2 with N, N-chelators (TaiMe= 1-methyl-2-(p-tolylazo) imidazole). Spectral and electrochemical characterisation of the products. Journal of Chemical Sciences, 2001, 113(3): 173-183.
Crossref Google Scholar
[28]
R.A. Oatto, S. Yamal, An elements of magnetic chemistry, 2nd ed. East West press, 1993: 101.
[29]

S. Subramanian, N. Rammaswamy, and B. Kartha, Synthesis of mononuclear Schiff base Cu(Ⅱ), Ni(Ⅱ), Co(Ⅱ) and Mn(Ⅱ) complexes and their application for DNA cleavage and antibacterial agent. Chem. Sci. Rev. Lett. , 2015, 14(13): 121-128.
Google Scholar
[30]

S. S Mary, S. Shobana, and J. Dharmaraja, In vitro microbial and antioxidant activities of Mn(Ⅱ) mixed ligand complexes. J. Chem. Pharm. Res. , 2016, 8(1S): 12-18.
Google Scholar
[31]

R.S. Joseyphs, M.S. Nair, Antibacterial and antifungal studies on some Schiff base complexes of Zn(Ⅱ). Mycobiology, 2008, 36(2): 93-98.
Crossref Google Scholar
[32]

N. Raman, D.J. Raja, and A. Sakthivel, Synthesis, spectral characterization of Sciff base transition metal complexes; DNA cleavage and antimicrobial activity studies. J. Chem. Sci. , 2007, 119(4): 303-309.
Crossref Google Scholar
[33]

A.A. Algon, S.S. Chyad, perilipin-1 level as risk marker of insulin resistance in morbidly obese patients. Nano Biomed. Eng. , 2017, 9(4): 285-290.
Crossref Google Scholar
[34]

R.S. Al-Zabeba, E. Grulke, Interaction of calcium phosphate nanoparticles with human chorionic gonadotropin modifies secondary and tertiary protein structure. Nova Biotechnologica et Chimica, 2015, 14(2): 141-157.
Crossref Google Scholar
[35]

R.K. Al-Shemary, B.A. Zaidan, Preparation and characterization of some transition metal complexes of new tetradentate Schiff base ligand type N2O2. Sch. Acad. J. BioSci. , 2016, 4(1): 18-26.
Google Scholar
[36]

N. Salih, J. Salimon, and E. Yousif, Synthesis, characterization and antimicrobial activity some carbamothioyl 1, 3, 4-thiadiazole derivatives. International J. Pharm. Tech. Res. , 2012, 4(2): 655-660.
Google Scholar
Nano Biomedicine and Engineering
Volume 10 Issue 1,
March 2018
Pages 46-55
DOI: 10.5101/nbe.v10i1.p46-55
Cite this article:
Al-Muhanaa SS, Al-Khafagy AH. Preparation and Biological Activities of New Heterocyclic Azo Ligand and Some of Its Chelate Complexes. Nano Biomedicine and Engineering, 2018, 10(1): 46-55. https://doi.org/10.5101/nbe.v10i1.p46-55

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Received: 22 February 2018
Accepted: 22 March 2018
Published: 26 March 2018
© Siham Sami Al-Muhanaa, Abbas Hmood Al-Khafagy

This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
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