World Journal of Organic Chemistry
ISSN (Print): 2372-2150 ISSN (Online): 2372-2169 Website: Editor-in-chief: Subrata Shaw
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World Journal of Organic Chemistry. 2015, 3(1), 1-8
DOI: 10.12691/wjoc-3-1-1
Open AccessArticle

Synthesis, Characterization and Antifungal Activity of Some Metal Complexes Derived From Quinoxaloylhydrazone

Ahmed Mahal1, 2, , Rajab Abu-El-Halawa3, 4, , Sami A. Zabin5, Mohammad Ibrahim3, Mahmoud Al-Refai3 and Tawfeq Kaimari6

1Department of Chemistry, Sultan Qaboos University, Muscat, Sultanate of Oman

2Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Napoli, Italy

3Department of Chemistry, Al al-Bayt University, Mafraq, Jordan

4Clinical Pharmacy, Al-Baha University, Al Baha, Saudi Arabia

5Department of Chemistry, Al-Baha University, Al Baha, Saudi Arabia

6Faculty of Pharmacy & Medical Science, Hebron University, Hebron, Palestine

Pub. Date: February 08, 2015

Cite this paper:
Ahmed Mahal, Rajab Abu-El-Halawa, Sami A. Zabin, Mohammad Ibrahim, Mahmoud Al-Refai and Tawfeq Kaimari. Synthesis, Characterization and Antifungal Activity of Some Metal Complexes Derived From Quinoxaloylhydrazone. World Journal of Organic Chemistry. 2015; 3(1):1-8. doi: 10.12691/wjoc-3-1-1


New Complexes of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and Tin(II) with 3-methyl-2-(pyridine-2-yl-methylene-hydrazinocarbonyl)quinoxaline-4-oxide (LHP) and 2-(2-hydroxy benzylidene-hydrazinocarbonyl)-3-methylquinoxaline-4-oxide (LHS) were prepared. The new complexes were characterized by elemental analysis, conductivity, magnetic measurements, IR and UV-Vis spectroscopic measurements. The results indicate 1:1 [M:L] chelates with the general formula [M(LHP)Cl2].nH2O where: M = Mn(II), n=4, Co(II), n=1/2, Cu(II), n=1, Hg(II), n=1, and 1:2 [M:L] in case of [M(LHS)2](OAc)2.nH2O when M = Zn(II), n= 3, Cd(II), n= 1, Hg(II), n= 1/2. The tin complex structure is suggested to be [Sn(LHP)2]Cl2.2H2O, while copper produces [Cu2(LHS)2SO4].H2O complexes. Also, the formula for mercuric complex found to be [Hg(LHS)2Cl2].2H2O. The magnetic moment measurements and electronic spectra suggest octahedral geometry for the prepared complexes. The antifungal investigation reveals that the activity was enhanced by chelation. The Cu(II) complexes has the highest inhibition zone against A. niger. But, the antifungal activity was weaker than the standard drug used.

aroyl hydrazone quinoxaline-4-oxide schiff bases metal complexes antifungal activity

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[1]  A. Golcu, M. Tumer, H. Demirelli, and R.A. Wheatley, Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorg. Chim. Acta, 358, 1797, (2005).
[2]  W. Rehman, F. Saman, and I. Ahmad, Synthesis, characterization, and biological study of some biologically potent Schiff Base transition metal complexes. Russ. J. Coord. Chem., 34(9), 678-682, (2008).
[3]  P.K. Panchal, P.B. Pansuriya, and M.N. Patel, In-vitro biological evaluation of some ONS and NS donor Schiff’s bases and their metal complexes. J. Enzy. Inhib. Med. Ch., 21(4), 453-458, (2006).
[4]  R. Abu-El-halawah, B.A. Fares, S.K. Fares, H. Baker, M. Qandil, M. Al-Refai, M. Ibrahim, Z. Juddeh, and K. Al-Obaidi, J. Coord. Chem., 57(13), 1139-1149, (2004).
[5]  R. Abu-El-Halawa, M. Al-Nuri, and F. Mahmoud. Asian J. Chem., 19(3), 1658-1666, (2007).
[6]  A.A. El-Sherif, Shoukry M.M., and Mohamed M.A. Abd-Elgawad, Synthesis, characterization, biological activity and equilibrium studies of metal(II) ion complexes with tridentate hydrazone ligand derived from hydralazine. Spectrochim. Acta A., 98, 307-321, (2012).
[7]  M.V. Angelusiu, S.F. Barbuceanu, C. Draghici, and G.L. Almajan, New Cu(II), Co(II), Ni(II) complexes with aroyl-hydrazone based ligand. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation. Eur. J. Med. Chem., 45 2055-2062, (2010).
[8]  N.M. Hosney, M.A. Mahmoud, and M.R.E. Aly, 2-ydroxybenzaldehyde-(4,6-Dimethylquinolin-2-yl)-Hydrazone (HBDH), Synthesis, Characterization, andLigational Behavior Towards Some Metals. Synth. React. Inorg. Me., 40, 439-446, (2010).
[9]  S. Vogel, D. Kaufmanna, M. Pojarováa, C. Müller, T. Pfaller, S. Kühne, P. J. Bednarski, and E.V. Angerer, Aroyl hydrazones M.of 2-phenylindole-3-carbaldehydes as novel antimitotic agents. Bioorgan. Med. Chem., 16, 6436-6447, (2008).
[10]  F. Grande, F. Aiello, O. De Grazia, A. Brizzi, A. Garofalo, and N. Neamati, Synthesis and antitumor activities of a series of novel quinoxalinehydrazides. Bioorg. Med. Chem., 15, 288-294, (2007).
[11]  D.S. Kalinowski, P.C. Sharpe, P.V. Bernhardt, and D.R. Richardson, Structure–Activity Relationships of Novel Iron Chelators for the Treatment of Iron Overload Disease: The Methyl Pyrazinylketone Isonicotinoyl Hydrazone Series. J. Med. Chem., 51, 331-344, (2008).
[12]  A.M. Stadler, and J.Harrowfield, Bis-acyl-/aroyl-hydrazones as multidentate ligands. Inorg. Chim. Acta, 362, 4298-4314, (2009).
[13]  W. Jing-lin, Z Ya-qin., Y.Bin-sheng, Transition metal complexes of asymmetrical aroyl-hydrazone ligand: Syntheses, structures, DNA binding and cleavage studies. Inorg. Chim. Acta, 409 484–496, (2014).
[14]  D.R. Richardson, and P.V. Bernhardt, Crystal and molecular structure of 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: an iron chelator with anti-tumour activity J. Biol. Inorg. Chem. 4 266-273, (1999).
[15]  L. Ronconi, and P.J. Sadler, Using coordination chemistry to design new medicines. Coordin. Chem. Rev., 251, 1633-1648, (2007).
[16]  S. Naskar, S. Naskar, S. Mondal, P.K. Majhi, M.G.B. Drew, and S.K.Chattopadhyay, Synthesis and Spectroscopic Properties of Cobalt(III) Complexes of some Aroyl Hydrazones: X-ray Crystal Structures of one Cobalt(III) Complex and Two Aroyl Hydrazone Ligands. Inorg. Chim. Acta, 371 100-106, (2011).
[17]  S. Sinha, A.K. Srivastava, S.K. Sengupta, and O.P. Pandey, Microwave Assisted Synthesis, Spectroscopic and Antibacterial Studies of Bis(cyclopentadienyl)hafnium (IV) Derivatives with Bezil Bis(aroyl hydrazones). Transit. Met. Chem., 33, 563-568, (2008).
[18]  H.H. Monfareda,, N.A. Lalami, A. Pazio, K. Wozniak, and C. Janiakc, Dinuclear Vanadium, Copper, Manganese And Titanium Complexes Containing O,O,N-Dichelating Ligands: Synthesis, Crystal Structure And Catalytic Activity. Inorg. Chim. Acta. 406, 241-250, (2013).
[19]  E. Macková, K. Hrušková, P. Bendová, A. Vávrová, H. Jansová, P. Hašková, P. Kovarˇíková, K. Vávrová, and T.Šimu˚nek, Methyl And Ethyl Ketone Analogs of Salicylaldehyde Isonicotinoyl Hydrazone: Novel Iron Chelators With Selective Antiproliferative Action. Chem-Biol. Interact.197, 69-79, (2012).
[20]  A. Casoli, A. Mangia, G. Mori, and G. Predieri, Liquid-Liquid Extraction And Determination Of Uranium (VI) With 2,6-Diacetylpyridine Bis(Benzoylhydrazone). Anal. Chim. Acta, 186, 283-287, (1986).
[21]  K.K. Rajac, N.I. Gandhi, L. Lekha, D. Easwaramoorthye, and G. Rajagopal, Synthesis, Spectral, Electrochemical And Catalytic Properties Of Ru(III) Schiff Base Complexes Containing N, O Donors. J. Mol. Struct., 1060 49-57, (2014).
[22]  M. Turkyilmaz, M. Kacan, and Y. Barana, Structure, Spectroscopic, Thermal Properties And Catalytic Activity of Iron(III)-Schiff Base Complexes. Inorg Chim Acta, 395, 255-259, (2013).
[23]  Z. Li, L. Lianga, L. Yanga, H. Chena, and X. Zhoua, Asymmetric Epoxidation Catalyzed By Cr(III)-Binaphthyl Schiff Base Complexes. J. Mol. Catal. A-Chem., 235, 108-113, (2005).
[24]  M.F. Ibrahim, Synthesis Of Some Quinoxaline Derivatives, M. Sc. Thesis, Al al-Bayt University, Mafraq, Jordan, (2002).
[25]  S. Mondal, S. Naskar, A.K. Dey, E. Sinn, C. Eribal, S.R. Herron, and S.K. Chattopadhyay, Mononuclear And Binuclear Cu(II) Complexes Of Some Tridentate Aroyl Hydrazones. X-Ray Crystal Structures of A Mononuclear And A Binuclear Complex. Inorg. Chim. Acta, 398, 98-105, (2013).
[26]  A.A.R. Despaigne, L.F.Vieira, I.C. Mendes, F.B. Costa, N.L. Speziali, and H. Beraldo, Organotin(IV) Complexes With 2-Acetylpyridine Benzoyl Hydrazones: Antimicrobial Activity. J. Braz. Chem. Soc., 21(7), 1247-1257, (2010).
[27]  A. Rahman, M.I. Choudry, W.J. Thomsen, Bioassay Techniques for Drug Development, Harwood Academic Publishers, Netherlands, (2001).
[28]  N.N. Emmanuel, A. Husian, F. Majoumo-Mbe, I.N. Njah, O.E. Offiong, and S. A. Bourne, Synthesis, Crystal Structure And Antifungal Activity Of A Ni(II) Complex Of A New Hydrazone Derived From Antihypertensive Drug Hydralazine Hydrochloride. Polyhedron, 63, 207-213, (2013).
[29]  R.K. Mohapatra, U.K. Mishra, S.K. Mishra, A. Mahapatra, and D.C. Dash, Synthesis And Characterization Of Transition Metal Complexes With Benzimidazolyl-2-Hydrazones Of O-Anisaldehyde And Furfural. Journal of the Korean Chem. Soc., 55(6), 926-931, (2011).
[30]  S. Biswas, T. Kar, S. Sarkar, and K. Dey, Synthesis, Characterization, And Density Functional Study Of Some Manganese(III) Schiff-Base Complexes. J. Coord. Chem., 65(6), 980-993, (2012).
[31]  C.M. Armstrong, P.V. Bernhardt, P. Chin, and D.R. Richardson, Structural Variations And Formation Constants Of First-Row Transition Metal Complexes Of Biologically Active Aroylhydrazones. Eur. J. Inorg. Chem., 1145-1156, (2003).
[32]  B. Mondal, M.G.B. Drew, and T. Ghosha, Synthesis, Structure And Solution Chemistry of Dioxidovanadium(V) Complexes With A Family Of Hydrazone Ligands. Evidence of Formation of Centrosymmetric Dimers via H-Bonds in the Solid State. Inorg. Chim. Acta, 363, 2296-2306, (2010).
[33]  H. Hosseini-Monfared, R. Bikas, and P. Mayer, Homogeneous Green Catalysts For Olefin Oxidation By Mono Oxovanadium(V) Complexes Of Hydrazone Schiff Base Ligands. Inorg. Chim. Acta, 363, 2574-2583, (2010).
[34]  N.M. Hosny, N.M. (E)-N-(1-Phenylethylidene) Nicotinohydrazide (PNH) And Some Of Its Metal Complexes. J. Mol. Struct., 923, 98-102, (2009).
[35]  N. M. Hosny, Synthesis and Charcterization of Transition Metal Complexes Derived from (E)-(N)-(1-(Pyridine-2-yl)ethylidiene)benzohydrazide (PEBH).Synth. React. Inorg. Me., 41, 736-742, (2011).
[36]  G.G. Mohamed, M.M. Omar, A.A. Ibrahim, Biological Activity Studies on Metal Complexes of Novel Tridentate Schiff base Ligand. Spectroscopic and Thermal Characterization. Eur. J. Med. Chem., 44, 4801-4812, (2009).
[37]  K. Nakamoto. In Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, 6th ed., John Wiley and Sons, Inc., USA, (2009).
[38]  S. Chattopadhyay, M.G.B. Drew, and A. Ghosh, Methylene Spacer-Regulated Structural Variation in Cobalt(II/III) Complexes with Bridging Acetate and Salen- or Salpn-Type Schiff-Base Ligands. Eur. J. Inorg. Chem., 1693-1701, (2008).
[39]  A.S. El-Tabl, F.A. Aly, M.M.E. Shakdofa, and A.M.E. Shakdofa, Synthesis, Characterization, and Biological Activity Of Metal Complexes Of Azohydrazone Ligand, J. Coord. Chem., 63(4), 700-712, (2010).
[40]  N. Nawar, and N.M. Hosny, Transitionmetal Complexes of 2-Acetylpyridine O-Hydroxybenzoylhydrazone (Apo-OHBH): Their Preparation, Characterization and Antimicrobial Activity. Chem. Pharm. Bull., 47, 944, (1999).
[41]  E. Soleimani, Novel Complexes of Mn(II), Co(II), and Cu(II) with Ligand Derived from Dibromobenziloxime. Journal of the Chinese Chemical Society, 57, 653-658, (2010).
[42]  G.B. Bagihalli, P.S. Badami, and S.A. Patil, Synthesis, Spectral Characterization And In Vitro Biological Studies Of Co(II), Ni(II) And Cu(II) Complexes With A,2,4-Triazole Schiff Bases. J. Enzy. Inhib. Med. Ch., 24(2), 381-394, (2009).
[43]  F.A. Cotton, C. Murillo, G. Wilkinson, and M. Bochmann, “Advanced Inorganic Chemistry”, Wiley and Sons, New York, 6th ed. (1999).
[44]  M.S. Refat, and N.M. El-Metwaly, Spectral, Thermal And Biological Studies Of Mn(II) And Cu(II) Complexes With Two Thiosemicarbazide Derivatives. Spectrochim. Acta A., 92 336-346, (2012).
[45]  A.B.P. Lever, Crystal Field Spectra Inorganic Electronic Spectroscopy, 1st ed., Elsevier, Amsterdam, p. 249, (1968).
[46]  J. Singh, Anu, and N. Singh, Synthesis and Spectral Studies of Copper (II) and Manganese (II) Complexes Using 2-Hydroxybenzyl-(pyridine-2-carbo)Iminohydrazone and 2-Furyl(pyridine-2- carbo)Iminohydrazone: Evaluation of Their Magnetic, and Antimicrobial Properties. Journal of Spectroscopy, 2013, 1-8, (2013).
[47]  M. Tumer, D. Ekinci, F. Tumer, and A. Bulut, Synthesis, Characterization And Properties Of Some Divalent Metal(II) Complexes: Their Electrochemical, Catalytic, Thermal And Antimicrobial Activity Studies. Spectrochim. Acta A., 67, 916-929, (2007).
[48]  N. Dharmaraj, P. Viswanathamurthi, and K. Natarajan, Ruthenium(II) Complexes Containing Bidentate Schiff€ Bases And Their Antifungal Activity. Transit. Metal Chem., 26, 105-109, (2001).