OJIC  Vol.5 No.4 , October 2015
Synthesis and Characterization of Schiff Base Metal Complexes Derived from Cefotaxime with 1H-indole-2,3-dione (Isatin) and 4-N,N-dimethyl-aminobenzaldehyde
Abstract: This work involved the synthesis of two Schiff base derivatives of cefotaxime antibiotic (CFX) namely: [sodium3-(acetoxymethyl)-7-((Z)-2-(methoxyimino)-2-(2-((E)-2–oxoindolin-3-ylide-neamino) thiazol-4-yl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate]. (0.5) Methanol (LI) and [sodium3-(acetoxymethyl)-7-((2Z)-2-(2-(4-dimethylamino) benzylideneamino) thiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylate]. (0.5) Methanol (LII) from the condensation reaction of the antibiotic with 1H-Indole-2,3-dione(isatin) and -N, N-dimethyl amino benzaldehyde respectively. Metal complexes of the two Schiff base ligands with Co(II), Ni(II), Cu(II), Cd(II), Pd(II) and Pt(IV) ions were prepared by reacting each ligand with the metal salts in refluxing ethanol. The chemical structures of the two ligands as well as the stereo-chemical structures and geometries of the studied metal complexes were suggested depending the results obtained from CHN and TG analysis, NMR, FTIR, and atomic absorption spectrophotometry, electronic spectra, magnetic moments and conductivity measurements. The mole ratio of the ligands to the metal ion was 1:1 with tridentate bonding behaviors of the coordinating ligands with the metal ions.
Cite this paper: Abdulghani, A. and Hussain, R. (2015) Synthesis and Characterization of Schiff Base Metal Complexes Derived from Cefotaxime with 1H-indole-2,3-dione (Isatin) and 4-N,N-dimethyl-aminobenzaldehyde. Open Journal of Inorganic Chemistry, 5, 83-101. doi: 10.4236/ojic.2015.54010.

[1]   Naz, N. and Iqbal, M.Z. (2011) Synthesis, Spectroscopic and Biological Studies of Transition Metal Complexes of Novel Schiff Bases Derived from Cephradine and Sugars. Science International (Lahore), 23, 27-31.

[2]   Bukhari, I.H., Arif, M., Akbar, J. and Khan, A.H. (2005) Preparation, Characterization and Biological Evaluation of Schiff Base Transition Metal Complexes with Cephradine. Pakistan Journal of Biological Sciences, 8, 614-617.

[3]   Anacona, J.R., Calvo, J. and Almanza, O.A. (2013) Synthesis, Spectroscopic and Magnetic Studies of Mono- and Poly- nuclear Schiff Base Metal Complexes Containing Salicilydene-Cefotaxime Ligand (H2L). International Journal of Inorganic Chemistry, 2013, Article ID: 108740, 7 p.

[4]   Kshash, A.H. (2010) Synthesis of Some Schiff Bases by Direct Condensation for Cefotaxime (Claforan) and Benzaldehyde or Its Substitutions and Study of Their Antibacterial Activity. Journal of Anbar Veterinary Science, 3, 125-132.

[5]   Al-Noor, T.H., Al-Jeboori, A.T. and Aziz, M.R. (2013) Preparation, Characterization and Antimicrobial Activities of Fe(II), Co(II), Ni(II), Cu(II), and Zn(II) Mixed Ligand Complexes Schiff Base Derived from Cephalexin Drug and 4(Dimethylamino) Benzaldehyde with Nicotinamide. Advances in Physics Theories and Applications, 18, 1-8.

[6]   Nigam, P., Mohan, S.W., Kundu, S. and Prakash, R. (2009) Trace Analysis of Cefotaxime at Carbon Paste Electrode Modified with Novel Schiff Base Zn(II) Complex. Talanta, 77, 1426-1431.

[7]   Bhrigu, B., Pathak, D., Siddiqui, N., Alam, M.S. and Ashen, W. (2010) Search for Biologically Active Isatins: A Short Review. International Journal of Pharmaceutical Science and Drug Research (IJPSDR), 2, 229-235.

[8]   Pal, M., Sharma, N.K. and Jha, P.K.K. (2011) Synthetic and Biological Multiplicity of Isatin: A Review. Journal of Advanced Scientific Research, 2, 35-44.

[9]   Aditya, J., Patidar, A., Manocha N. and Gupta, D. (2012) Synthesis, Characterization and Antimicrobial Activity of Novel Schiff Base of Isatin Derivatives. International Journal of Pharmaceutical Science and Drug Research (IJPSDR), 4, 260-266.

[10]   Verma, M., Pandeya, S.N., Singh, K.N. and Stables, J.P. (2004) Anticonvulsant Activity of Schiff Bases of Isatin Derivatives. Acta Pharmaceutica, 54, 49-56.

[11]   Silva, J.F.M., Garden, S.J. and Pinto, A.C. (2001) The Chemistry of Isatins a Review from 1975 to 1999. Journal of Brazilian Chemical Society, 12, 273-324.

[12]   Mishra, A.P., Mishra, R., Jain, R. and Gupta, S. (2012) Synthesis of New VO(II), Co(II), Ni(II) and Cu(II) Complexes with Isatin-3-Chloro-4-Floroaniline and 2-Pyridinecarboxylidene-4-Aminoantipyrine and Their Antimicrobial Studies. Mycobiology, 40, 20-26.

[13]   Rochow, E.G. (1960) Inorganic Synthesis. McGraw-Hill, New York, 6, 218.

[14]   Venkateshwarlu, E., Venkateshwar, J.R., Umasankar, K. and Dheeraj, G. (2012) Study of Anti-Inflamatory, Analgesic and Anti-Pyretic Activity of Novel Isatin Derivatives. Asian Journal of Pharmaceutical and Clinical Research, 5, 187-190.

[15]   Silverstien, R.M., Webster, F.X. and Kiemle, D.J. (2005) Spectrophotometric Identification of Organic Compounds. 7th Edition, John Wiley and Sons, Inc., New York.

[16]   Ikotun, A.A., Egharevba, G.O., Obafemi, C.A. and Owoseni, A.O. (2012) Ring Deactivating Effect on Antimicrobial Activities of Metal Complexes of the Schiff Base of p-Nitroaniline and Isatin. Journal of Chemical and Pharmaceutical Research, 4, 416-422.

[17]   Chohan, Z.H. and Jaffery, M.F. (2000) Synthesis, Characterization and Biological Evaluation of Co(II), with Cu(II), Ni(II) and Zn(II) Complexes Cephradine. Metal Based Drugs, 7, 265-269.

[18]   Anacona, J.R. and Silva, G.D. (2005) Synthesis and Antibacterial Activity of Cefotaxime Metal Complexes. Journal of the Chilean Chemical Society, 50, 447-450.

[19]   Al-Resayes, S.I., Shakir, M., Abbasi, A., Amin, K.M.Y. and Lateef, A. (2012) Synthesis, Spectroscopic Characterization and Biological Activities of N4O2 Schiff Base Ligand and Its Metal Complexes of Co(II), Ni(II), Cu(II) and Zn(II). Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy, 93, 86-94.

[20]   Kumar, A. and Singh, D. (2009) Metal Complexes with the Fluoroquinolone Antibacterial Agent Norfloxacin, Synthesis, Structure and Bioactivity. International Journal of Chemical Sciences, 7, 19-27.

[21]   Joshi, S. (2011) Synthesis, Characterization and Biological Studies of Schiff Base Metal Complexes of Co (II), Zn (II), Ni (II), and Mn (II) Derived from Amoxicillin Trihydrate with Various Aldehydes. International Journal of Pharma and Bio Sciences, 2, 240-250.

[22]   Nagajothi, A., Kiruthika, A., Chitra, S. and Parameswari, K. (2012) Synthesis and Characterization of Tetradentate Co(II) Schiff Base Complexes: Antimicrobial and DNA Cleavage Studies. International Journal of Research in Pharmaceutical and Biomedical Sciences, 3, 1768-1778.

[23]   Chaluvaraju, K.C. (2011) Synthesis and Biological Evaluation of Some Isatin Derivatives for Antimicrobial Properties. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 2, 541-546.

[24]   Prakash, C.R., Raja, S., Selvam, T.P., Saravanan, G., Karthick, V. and Kumar, P.D. (2009) Synthesis and Antimicrobial Activities of Some Novel Schiff Bases of 5-Substituted Isatin Derivatives. Rasayan Journal of Chemistry, 2, 960-968.

[25]   Khalil, M.M.H. and Al-Seif, F.A. (2008) Molybdenum and Tungsten Tricarbonyl Complexes of Isatin with Triphenylphosphine. Research Letters in Inorganic Chemistry, 2008, Article ID: 746058, 4 p.

[26]   Parnâu, C., Kriza, A., Popa, N. and Udrea, S. (2005) Controlled Synthesis III. Reaction of Sn(IV) and Zr(IV) with Isatins. Analele UniversitaNii din Bucuresti-Chimie, Anul XIV (Serienoua), I-II, 141-146.

[27]   Sharma, A. and Shah, M. (2013) Synthesis and Characterization of Some Transition Metal Complexes Derived from Bidentate Schiff Base Ligand. Journal of Applied Chemistry, 3, 62-66.

[28]   Sultana, N., Arayna, M.S. and Afzal, M. (2003) Synthesis and Antibacterial Activity of Cepharadine Metal Complexes: Part I: Complexes with Magnesium, Calcium, Chromium and Manganese. Pakistan Journal of Pharmaceutical Sciences, 16, 59-72.

[29]   Sultana, N., Arayna, M.S. and Afzal, M. (2005) Synthesis and Antibacterial Activity of Cephradine Metal Complexes: part II Complexes with Cobalt, Copper, Zinc and Cadmium. Pakistan Journal of Pharmaceutical Sciences, 18, 36-42.

[30]   Imran, M., Iqbal, J., Iqbal, S. and Ijaz, N. (2007) In Vitro Antibacterial Studies of Ciprofloxacin-Imines and Their Complexes with Cu(II),Ni(II),Co(II), and Zn(II). Turkjsh Journal of Biology, 31, 67-72.

[31]   Anacona, J.R. and Lopez, M. (2012) Mixed-Ligand Nickel(II) Complexes Containing Sulfathiazole and Cephalosporin Antibiotics: Synthesis, Characterization, and Antibacterial Activity. International Journal of Inorganic Chemistry, 2012, Article ID: 106187.

[32]   El-Said, A.I., Aly, A.A.M., El-Meligy, M.S. and Ibrahim, M.A. (2009) Mixed Ligand Zinc (II) and Cadmium(II) Complexes Containing Ceftriaxone or Cephradine Antibiotics and Different Donors. Journal of the Argentine Chemical Society, 97, 149-165.

[33]   Singh, D.P., Grover, V., Kumar, K. and Jain, K. (2010) Metal Ion Prompted Macrocyclic Complexes Derived from Indole-2,3-Dione (Isatin) and O-Phenylenediamine with Their Spectroscopic and Antibacterial Studies. Acta Chimica Slovenica, 57, 775-780.

[34]   Anacona, J.R. and Osorio, I. (2008) Synthesis and Antibacterial Activity of Copper(II) Complexes with Sulphathiazole and Cephalosporin Ligands. Transition Metal Chemistry, 33, 517-521.

[35]   Nakamoto, K. (1997) Infrared and Raman Spectra of Inorganic and Coordination Compounds. 5th Edition, John Wiley and Sons, Inc., New York.

[36]   Sultana, N. and Arayne, M.S. (2007) In Vitro Activity of Cefadroxil, Cephalexin, Cefatrizine and Cefpirome in Presence of Essential and Trace Elements. Pakistan Journal of Pharmaceutical Sciences, 20, 305-310.

[37]   Khalifa, M.A. and Hussaan, A.M. (1996) Complexes of Some Metal Ions of Schiff Base Ligand Derived from Isatin with 2-Aminothiophenol. Journal of the Chemical Society of Pakistan, 18, 115-118.

[38]   Sutton, D. (1968) Electronic Spectra of Transition Metal Complexes. McGraw-Hill Publ. Co. Ltd., New York.

[39]   Lever, A.B.P. (1968) Inorganic Electronic Spectroscopy. Elsevier Publishing Company, Amsterdam, London.

[40]   Figgis, B.N. (1966) Introduction to Ligand Fields. Inter-Science Publishers, a Division of John Wiley and Sons, New York, London, Sydney.

[41]   Sinthuja, S.A. and Kumari, S.S. (2013) Synthesis, Spectroscopic Investigation and Antimicrobial Studies on Some Schiff Base Complexes of Cu(II) and Ni(II). Journal of Chemical and Pharmaceutical Research, 5, 303-309.

[42]   Hegazy, W.H. and Gaafa, A.E.D.M. (2012) Synthesis, Characterization and Antibacterial Activities of New Pd(II) and Pt(IV) Complexes of Some Unsymmetrical Tetradentate Schiff Bases. American Chemical Science Journal, 2, 86-99.

[43]   Geary, W.J. (1971) The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 7, 81-122.

[44]   Ignat, I., Oprea, O., Stanica, N. and Kriza, A. (2012) Synthesis, Characterization and Thermal Behavior of Complexes of Cu(II), Co(II), Ni(II), Zn(II) and Cd(II) with Schiff Base Derived from 1-H-Indole-2,3-Dione and o-Aminobenzylic Alcohol. Revista De Chimie, 63, 1001-1007.

[45]   Parnau, C., Olar, R., Badea, M. and Kriza, A. (2006) Thermal Behavior of Some New Isatin Complexes. Journal of Thermal Analysis and Calorimetry, 86, 217-221.