Metal complexes of hydrazones and their biological, analytical and catalytic applications: A review

Main Group Chemistry

Volumn 13, Issue 3, 2014, Pages 187-218

  Shakdofa, Mohamad M E ^a,b   Shtaiwi, Majed H ^a   Morsy, Nagy ^a,b   Abdel Rassel, Tayseer M A ^a,c  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c Suez Canal University   (Egypt)

Author keywords

analytical; biological; catalytic application; Hydrazones; Transition metal complexes

Indexed keywords

EID: 84930620611     PISSN: 10241221     EISSN: 17451167     Source Type: Journal    
DOI: 10.3233/MGC-140133     Document Type: Review

References (142)

1. R.R. Singh, P. Jam and R.P. Singh, Hydrazones as analytical reagents, Talanta 29 (1982), 77.
2. Y.M. Issa, R.M. Issa, S.A. Abd El-Latif and H.A. Abd El-Salam, Structural studies of Cu(II) chelates with some arylidene derivatives of benzilic hydrazide, Monatshefte Fur Chemie 129 (1998), 19.
3. D.R. Richardson, Cytotoxic analogs of the iron(III) chelator pyridoxal isonicotinoyl hydrazone: Effects of complexation with copper(II), gallium(III), and iron(III) on their antiproliferative activities, Antimicrobial Agents & Chemotherapy 41 (1997), 2061.
4. D.R. Richardson, Iron chelators as therapeutic agents for the treatment of cancer, Critical Reviews in Oncology/Hematology 42 (2002), 267.
5. D.R. Richardson and P.V. Bernhard, Crystal and molecular structure of 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and its iron(III) complex: An iron chelator with anti-tumour activity, JBIC 4 (1999), 266.
6. D.B. Lovejoy and D.R. Richardson, Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells, Blood 100 (2002), 666.
7. J. Yuan, D.B. Lovejoy and D.R. Richardson, Novel di-2-pyridyl-derived iron chelators with marked and selective antitumor activity: In vitro and in vivo assessment, Blood 104 (2004), 1450.
8. P.V. Bernhardt, L.M. Caldwell, T.B. Chaston, P. Chin and D.R. Richardson, cytotoxic iron chelators: Characterization of the structure, solution chemistry and redox activity of ligands and iron complexes of the di-2-pyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues, J Biol Inorg Chem 8 (2003), 866.
9. E.M. Becker, D.B. Lovejoy, J.M. Greer, R. Watts and D.R. Richardson, Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents, British J Pharm 138 (2003), 819.
10. P. Vicini, M. Incerti, I.A. Doytchinova, P.L. Colla, B. Busonera and R. Loddo, Synthesis and antiproliferative activity of benzo [d]isothiazole hydrazones, Eur J Med Chem 41 (2006), 624.
11. D.K. Johnson, T.B. Murphy and N.J. Rose, Cytotoxic Chelators and Chelates 1. Inhibition of DNA Synthesis in cultured rodent and human cells by aroylhydrazones and by a Copper(II) Complex of Salicylaldehyde Benzoyl Hydrazone Inorg, Chim Acta 67 (1982), 159.
12. D.V. Rayk, S. Sarel and N. Hunt, Inhibition of in vitro lymphoproliferation by three novel iron chelators of the pyridoxal and salicyl aldehyde hydrazone classes, Biochem Pharm 60 (2000), 581.
13. J. Easmon, G. Puerstinger, T. Roth, H.-H. Fiebig, M. Jenny, G. Heinish and J. Hofmann, 2-benzoxazolyl and 2-benzimidazolyl hydrazones derived from 2-acetylpyride, Int J Cancer 94 (2001), 89.
14. S.A.M. El-Hawash, A.E. AbdelWahab and M.A. El-Demellawy, Cyanoacetic acid hydrazones of 3-(and 4-) acetylpyridine and some derived ring systems as potential antitumor and anti-HCV agents, Arch Pharm Chem Life Sci 339 (2006), 14.
15. N. Terzioglu and A. Gürsoy, Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo,[1,3,4]thiadiazole-5-carbohydrazide, Eur J Med Chem 38 (2003), 781.
16. M.T. Cocco, C. Congiv, V. Lilliu and V. Onnis, Synthesis and in vitro antitumoral activity of new hydrazinopyrimidine-5-carbonitrile derivatives, Bioorg Med Chem 14 (2006), 366.
17. M. Hong, H. Yin, X. Zhang, C. Li, C. Yue and S. Cheng, Di-and tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoyl hydrazone: Synthesis, characterization and in vitro antitumor activities, J Organomet Chem 724 (2013), 23.
18. E. Macková, K. Hrusková, P. Bendová, A. Vávrová, H. Jansová, P. Hasková, P. Kovaríková, K. Vávrová and T. Sim°unek, Methyl and ethyl ketone analogs of salicylaldehyde isonicotinoyl hydrazone: Novel iron chelators with selective antiproliferative action, Chemico-Biological Interactions 197 (2012), 69.
19. S.S. Machakanur, B.R. Patil, D.S. Badiger, R.P. Bakale, K.B. Gudasi and S.W.A. Bligh, Synthesis, characterization and anticancer evaluation of novel tri-arm starshaped 1,3,5-triazine hydrazones, J Mole Struct 1011 (2012), 121.
20. S. Mukherjee, S. Chowdhury, A. Ghorai, U. Ghosh and H. Stoeckli-Evans, Synthesis, structure, interaction with DNA and cytotoxicity of a luminescentcopper(II) complex with a hydrazone ligand, Polyhedron 51 (2013), 228.
21. P. Sathyadevi, P. Krishnamoorthy, N.S.P. Bhuvanesh, P. Kalaiselvi, V.V. Padma and N. Dharmaraj, Organometallic ruthenium(II) complexes: Synthesis, structure and influence of substitution at azomethine carbon towards DNA/BSA binding, radical scavenging and cytotoxicity, Eur J Med Chem 55 (2012), 420.
22. A.S. Abu-Surrah, K.A. Abu Safieh, I.M. Ahmad, M.Y. Abdalla, M.T. Ayoub, A.K. Qaroush and A.M. Abu-Mahtheieh, New palladium(II) complexes bearing pyrazole-based Schiff base ligands: Synthesis, characterization and cytotoxicity, Eur J Med Chem 45 (2010), 471.
23. Z.-Chen Liu, B.-Dui Wang, B. Li, Q. Wang, Z.-Yin Yang, T.-Rong Li and Y. Li, Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases, Eur J MedChem 45 (2010), 5353.
24. Y. Zhang, L. Zhang, L. Liu, J. Guo, D. Wu, G. Xu, X. Wang and D. Jia, Anticancer activity, structure, and theoretical calculation of N-(1-phenyl-3-methyl-4-propyl-pyrazolone-5)-salicylidene hydrazoneand its copper(II) complex, Inorg Chim Acta 363 (2010), 289.
25. L. Mazur, B.M. Banachiewicz, R. Paprocka, M. Zimecki, U.E. Wawrzyniak, J. Kutkowska and G. Ziókowska, Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex-A potential antitumor drug, J Inorg Biochem 114 (2012), 55.
26. A. Datta, P.-Hsin Liu, J.-Hsien Huang, E. Garribba, M. Turnbull, B. Machura, C.-Lin Hsu,W. Tang Chang and A. Pevec, End-to-end thiocyanato-bridged zig-zag polymers of CuII, CoII and NiII with a hydrazone ligand: EPR, magnetic susceptibility and biological study, Polyhedron 44 (2012), 77.
27. F. Kratz, U. Beyer, T. Roth, N. Tarasova, P. Collery, F. Lechenault, A. Cazabat, P. Schumacher, C. Unger and U. Falken, Transferrin conjugates of doxorubicin: Synthesis, characterization, cellular uptake, and in vitro efficacy, J Pharm Sci 87 (1998), 338.
28. "Tuberculosis Fact sheet No. 104" World Health Organization. Retrieved 26 July (2011).
29. T.R. Frieden, T.R. Sterling, S.S. Munsiff, C.J. Watt and C. Dye, Tuberculosis, Lancet 362 (2003), 887.
30. B.K. Kaymakçioglo and S. Rollas, Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones, Il Farmaco 57 (2002), 595.
31. S.G. Küçükgüzel, A. Mazi, F. Sahin, S. Ö ztürk and J. Stables, Synthesis and biological activities of diflunisal hydrazide/hydrazones, Eur J Med Chem 38 (2003), 1005.
32. S.G. Küç ükgüzel and S. Rollas, Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyrazoline-5-ones as potential antimycobacterial agents, Il Farmaco 57 (2002), 583.
33. V. Kumar, A.K. Abbas, N. Fausto and R.N. Mitchell, Robbins Basic Pathology, 8th ed, (2007), Saunders, Elsevier, pp. 516-522.
34. D. Sriram, P. Yogeeswari and K. Madhu, Synthesis and in vitro antitubercular activity of some 1-4-sub)phenyl]-3-(4-1-pyridine-4-carbonyl)hydrazono]ethylphenyl)thiourea, Bioorg Med Chem Lett 16 (2006), 876.
35. D. Sriram, P. Yogeeswari and K. Madhu, Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones, Bioorg Med Chem Lett 15 (2005), 4502.
36. B. Bottari, R. Maccari, F. Monforte, E. Rotondo and M.G.Vigorita, Isoniazid-related copper(II) and Nickel(II) Complexes with Antimycobacterial In Vitro Activity. Part 9, Bioorg Med Chem Lett 10 (2000), 657.
37. R. Maccari, R. Ottana and M.G. Vigorita, In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes: Part 14, Bioorg Med Chem Lett 15 (2005), 2509.
38. J. Patole, U. Sandbhor, S. Padhye, D.N. Deobagkar, C.E. Anson and A. Powell, Structural chemistry and in vitro antitubercular activity of acetylpyridine benzoyl hydrazone and its copper complex against mycobacterium smegmatis, Bioorg Med Chem Lett 13 (2003), 51.
39. B.D. Young and K. Duncan, Prospects for new interventions in the treatment and prevention of mycobacterial disease, Ann Rev Microbiol 49 (1995), 641.
40. Smith, Williams, Introduction to principles of drug design and action, Editor: H, John Smith; Third Edition, Harwood: New York, N. Y. 1997, p. 400.
41. D. Sriram, P. Yogeeswari and R.V. Devakaram, Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides, Bioorg Med Chem 14 (2006), 3113.
42. R.S. Hunoora, B.R. Patil, D.S. Badigera, R.S. Vadavia, K.B. Gudasia, V.M. Chandrashekhar and I.S. Muchchandi, Spectrochim, Acta Part A 77 (2010), 838.
43. D.S. Badiger, R.S. Hunoor, B.R. Patil, R.S. Vadavi, C.V. Mangannavar, I.S. Muchchandi, Y.P. Patil, M. Nethaji and K.B. Gudasi, Synthesis, spectroscopic properties and biological evaluation of transition metal complexes of salicylhydrazone of anthranilhydrazide: X-ray crystal structure of copper complex, Inorg Chim Acta 384 (2012), 197.
44. V.N. Telvekar, A. Belubbi, V.K. Bairwa and K. Satardekar, Novel N-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents, Bioorg Med Chem Lett 22 (2012), 2343.
45. R.B. Pathak, P.T. Chovatia and H.H. Parekh, Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives, Bioorg Med Chem Lett 22 (2012), 5129.
46. D. Shingnapurkar, P. Dandawate, C.E. Anson, A.K. Powell, Z. Afrasiabi, E. Sinn, S. Pandit, K.V. Swamy, S. Franzblau and S. Padhye, Synthesis and characterization of pyruvate-isoniazid analogs and their copper complexes as potential ICL inhibitors, Bioorg Med Chem Lett 22 (2012), 3172.
47. U. Sandbhor, S. Padhye, D. Billington, D. Rathbone, S. Franzblau, C.E. Anson and A.K. Powell, Metal complexes of carboxoamidrazone analogs as antitubercular agents:1. Synthesis, X-ray crystal-structure, spectroscopic properties and antimycobacterial activity against H37Rv cell line, J Inorg Biochem 90 (2002), 127.
48. S.K. Sridhar, M. Saravanan and A. Ramsh, Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives, Eur J Med Chem 36 (2001), 615.
49. C. Loncle, J.M. Brunel, N. Vidal, M. Dherbomez and Y. Letourneux, Synthesis and antifungal activity of cholesterolhydrazone derivatives, Eur J Med Chem 39 (2004), 1067.
50. P. Vicini, F. Zani, P. Cozzini and I. Doytchinova, Hydrazones of 1,2-benzisothiazole hydrazides: Synthesis, antimicrobial activity and QSAR investigations, Eur J Med Chem 37 (2002), 553.
51. P.G. Lawrence, P.L. Harold and O.G. Francis, Cefotaxime concentration in ascites, Antibiot Chemother (1980), 1597.
52. E.K. Efthimiadou, G. Psomas,Y. Sanakis, N. Katsaros and A. Karaliota, Metal complexes with the quinolone antibacterial agent N-propyl-norfloxacin: Synthesis, structure and bioactivity, J Inorg BioChem 101 (2007), 525.
53. H.S. Yang, Y. Bui, W.W. Ting, S.Q. Zhen and A.D. Rong, Crystal structure and bioactivity of complex [Gd(C10H9N2O4)(C10H8N2O4)(H2O)3]2.phen.4H2O, Chin J Chem 23 (2005), 1198.
54. V.K. Sharma and S. Srivastava, Synthesis, spectroscopic and antifungal studies of trivalent chromium, manganese, Iron and Cobalt complexes with hydrazones derived from benzil a-monoxime and various aromatic hydrazides, Synth React Inorg Met-Org Nano-Met Chem 35 (2005), 311.
55. S.K. Sengupta, O.P. Pandey, A.K. Srivastava, A. Bhatt and K.N. Mishar, Synthesis, physico-chemical and antimicrobial studies on acetylferrocenyl hydrazone derivatives of dichlorobis (cyclopentadienyl)hafnium(IV), Trans Met Chem 24 (1999), 703.
56. A. Cukuroval, I. Yilmaz, S. Gur and C. Kazaz, Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring, Eur J Med Chem 41 (2005), 201.
57. S. Rollas, N. Gulerman and H. Erdeniz, Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines, Il Farmaco 57 (2002), 171.
58. S.N. Khattab, Synthesis and biological activity of novel amino acid-(N'-Benzoyl) hydrazide and amino acid-(N'-Nicotinoyl) hydrazide derivatives, Molecules 10 (2005), 1218.
59. S. Konstantinovíc, B.C. Radovanovíc, Z Cakíc and V. Vasíc, Synthesis and characterization of Co(II), Ni(II), Cu(II) and Zn(II) complexes with 3-salicylidenehydrazono-2-indolinone, J Serb Chem Soc 68 (2003), 641.
60. O.M.I. Adly and A. Taha, Coordination diversity of new mononuclear ONS hydrazone with transitionmetals: Synthesis, characterization, molecular modeling and antimicrobial studies, J Mole Struct 1038 (2013), 250.
61. Ü .Ö . Ö zdemir, N. Akkaya and N. Ö zbek, Coordination diversity of new mononuclear ONS hydrazone with transition metals: Synthesis, characterization, molecular modeling and antimicrobial studies, Inorg Chim Acta 400 (2013), 13.
62. N.Ö zbek, S.Alyar,H.Alyar,E. Ş ahin andN.Karacan, Synthesis, characterization and anti-microbial evaluation ofCu(II), Ni(II), Pt(II) and Pd(II) sulfonylhydrazone complexes; 2D-QSARanalysis of Ni(II) complexes of sulfonylhydrazone derivatives, Spectrochim Acta Part A 108 (2013), 123.
63. A.A. El-Sherif, M.M. Shoukry and M.M.A. Abd-Elgawad, 2-(E)-[(2Z)-2-(1,2-Dihydrophthalazin-1-ylidene) hydrazinylidene]methylphenol, Spectrochim Acta Part A98 (2012), 307.
64. A.K. Sharma and S. Chandra, Synthesis, characterization, biological activity and equilibrium studies of metal(II) ion complexes with tridentate hydrazone ligand derived from hydralazine, Spectrochim Acta Part A 103 (2013), 96.
65. K.M. Ibrahim, R.R. Zaky, E.A. Gomaa and M.N. Abd El-Hady, Physicochemical studies and biological evaluation on (E)-3-(2-(1-(2-hydroxyphenyl) hydrazinyl)-3-oxo-N-(thiazol-2yl) propanamide complexes, Spectrochim Acta Part A107 (2013), 133.
66. M. Navarro, G. Gabbiani, L. Messori and D. Gambino, Drug Discovery Today 15 (2010), 1070.
67. D. Gambino, Potentiality of vanadium compounds as anti-parasitic agents, Coord Chem Rev 255 (2011), 2193.
68. WHO, Global Report on Antimalarial Efficacy and Drug Resistance, 2000-2010.
69. R.A. Sánchez-Delgado and A. Anzellotti, Metal complexes as chemotherapeutic agents against tropical diseases: Trypanosomiasis, malaria and leishmaniasis, Mini-Rev Med Chem 4 (2004), 23.
70. P. Melnyk, V. Lerouz, C. sergheraert and P. Grellier, Design, synthesis and in vitro antimalarial activity of an acylhydrazone library, Bioorg Med Chem Lett 16 (2006), 31.
71. S. Gemma, G. Kukreja, C. Fattorusso, M. Persico, M.P. Romano, M. Altarelli, L. Savini, G. Campiani, E. Fattorusso, N. Basilico, D. Taramelli, V. Yardley and S. Butini, Synthesis of N1-arylidene-N2-quinolyl-and N2-acrydinylhydrazones as potent antimalarial agents active against CQ-resistant P. falciparum strains, Bioorg Med Chem Lett 16 (2006), 5384.
72. A. Walcovrt, M. Loyevsky, D.B. Lovejoy, V.R. Gordeuk and D.R. Richardson, Novel aroylhydrazone and thiosemicarbazone iron chelatorswith anti-malarial activity against chloroquine-resistantand-sensitive parasites, Inter J Biochem Cell Biology 36 (2004), 401.
73. M. Singh and N. Raghav, Biological activities of hydrazones, Int J Pharm Pharm Sci 3 (2011), 26.
74. M. Gökçe, A.E. Geciken, E. Yildirim and A.U. Tosuni, Synthesis and anticonvulsant activity of 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o/p-substituted benzal) hydrazone derivatives, Arzneimittelforschung 58 (2008), 537.
75. S. Rollas and ŞG Küç ükgüzel, Molecules, biological activities of hydrazone derivatives, Molecules 12 (2007), 1910.
76. J.R. Dimmock, S.C. Vashishtha and J.P. Stables, Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds, Eur J Med Chem 35 (2000), 241.
77. B. Ç akir, Ö . Dag, E. Yildirim, K. Erol and M.F. Ş ahin, Synthesis and anticonvulsant activity of some hydrazones of 2-[(3H)-oxobenzoxazolin-3-ylaceto]hydrazide, J Fac Pharm Gazi 18 (2001), 99.
78. J. Ragavendran, D. Sriram, S. Patel, I. Reddy, N. Bharathwajan, J. Stables and P. Yogeeswari, Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore, Eur J Med Chem 42 (2007), 146.
79. P.K. Kadaba and Z. Lin, United States Patent No.-5,942,527; 1999.
80. S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives, Eur J Pharm Sci 16 (2002), 129.
81. M.T. Abdel-Aal, W.A. El-Sayed and E.H. El-Ashry, Synthesis and antiviral evaluation of some sugar arylglycinoylhydrazones and their oxadiazoline derivatives, Arch Pharm Chem Life Sci 339 (2006), 656.
82. T.M. Aminabhavi, N.S. Birader and C.S. Patil, Complexes of hydrazones with telhuium, Inorg Chim Acta 78 (1983), 107.
83. S.M. Sondhi, M. Dinodia and A. Kumar, Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives, Bioorg Med Chem 14 (2006), 4657.
84. R.S. Hoonur, B.R. Patil, D.S. Badiger, R.S. Vadavi, K.B. Gudasi, P.R. Dandawate, M.M. Ghaisas, S.B. Padhye and M. Nethaji, Transition metal complexes of 3-aryl-2-substituted 1,2-dihydroquinazolin-4(3H)-one derivatives: New class of analgesic and anti-inflammatory agents, Eur J Med Chem 45 (2010), 2277.
85. M. Gökçe, S. Utku and E. Küpeli, Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p-substituted/nonsubstituted benzal)hydrazone derivatives, Eur J Med Chem 44 (2009), 3760.
86. G. Faa and G. Crisponi, Iron chelating agents in clinical practice, Coord Chem Rev 184 (1999), 291.
87. J.T. Edward, Partition coefficient of the iron (III) compleses of pyridoxal isonictinyl hydrazone and its analogs and the correlation to iorn chelation efficicacy. Correction of some reported partition coefficients, Biometals 11 (1998), 203.
88. J.T. Edward, P. Ponka and D.R. Richardson, Partion coefficients of the iron(III)complexes of pyridoxal isoicotinoyl hydrazone and its analogsand the correlation to iron chelation efficacy, Biometals 8 (1995), 209.
89. E.M. Becker and D.R. Richardson, The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class, J Lab Clin Med 134 (1999), 510.
90. D.R. Richardson, The MCK mouse heart model of Friedreich's ataxia: Alterations in iron-regulated proteins and cardiac hypertrophy are limited by iron chelation, Biochim Biophys Acta 1536 (2001), 133.
91. C.S.M. Wong, J.C. Kwok and D.R. Richardson, PCTH: A novel orally active chelator of the aroylhydrazone class that induces iron excretion from mice, Biochim Biophys Acta 1739 (2004), 70.
92. T.B. Chaston and D.R. Richardson, Iron chelators for the treatment of iron overload disease: Relationship betweenstructure, redoxactivity, and toxicity, American J Hematology 73 (2003), 200.
93. P.V. Bernhardt, L.M. Caldwell, T.B. Chaston, P. Chin and D.R. Richardson, Cytotoxic iron chelators: Characterization of the structure, solution chemistry and redox activity of ligands and iron complexes of the di-2-pyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues, J Biol Inorg Chem 8 (2003), 866.
94. T.B. Chaston and D.R. Richordson, Interactions of the pyridine-2-carboxaldehyde isonicotinoyl hydrazone class of chelators with iron and DNA: Implications for toxicity in the treatment of iron overload disease, J Biol Inorg Chem 8 (2003), 427.
95. P.V. Bernhard, P. Chin, P.C. Sharpe, J.-Y.C.Wang and D.R. Richondson, Novel diaroylhydrazine ligands as iron chelators: Coordination chemistry and biological activity, J Biol Inorg 10 (2005), 761.
96. P. Pelagatti, M. Carcelli, C. Pelizzi and M. Costa, Polymerisation of phenylacetylene in water catalysed by Pd(NN-O)Cl complexes, Inorg Chim Acta 342 (2003), 323.
97. V. Tabernero, T. Cuenca and E. Herdtweck, Hydrazonide titanium derivatives: Synthesis, characterization and catalytic activity in olefin polymerization. Molecular structure of [Ti(5-C5H4SiMe3)Cl(-N2CPh2)]2, J Organomet Chem 663 (2002), 173.
98. L. Chen, J. Hou andW.-H. Sun, Ethylene oligomerization by hydrazone Ni(II) complexes/MAO, Appl Cataly 246 (2003), 11.
99. M.S. Niasari and A. Amiri, Synthesis and characterization of alumina-supported Mn(II), Co(II), Ni(II) and Cu(II) complexes of bis(salicylaldiminato)hydrazone as catalysts for oxidation of cyclohexene with tert-buthylhydroperoxide, Appl Cataly 290 (2005), 46.
100. A. El-Motaleb and M. Ramadan, Synthesis, characterization and ascorbic acid oxidase mimetic catalytic activity of copper(II) picolyl hydrazone complexes, Trans Met Chem 30 (2005), 471.
101. H.H. 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 (2010), 2574.
102. H.H.-Monfared, N.A.-Lalami, A. Pazio, K. Wozniak and C. Janiak, Chirality and diastereoselection of-/-configured tetrahedral zinc complexes with enantiopure or racemic Schiff base ligands, Inorg Chim Acta 408 (2013), 109.
103. M. Bagherzadeh, M. Zare, V. Amani, A. Ellern and L.K. Woob, Dioxo and oxo-peroxo molybdenum(VI) complexes bearing salicylidene 2-picoloyl hydrazone: Structures and catalytic performances, Polyhedron 53 (2013), 223.
104. D. Pandiarajan and R. Ramesh, Suzuki-Miyaura cross-coupling reaction of aryl bromides catalyzed by palladium(II) pyridoxal hydrazone complexes, J Organomet Chem 708-709 (2012) 18.
105. M.N.Kopylovich,T.C.O. Mac Leod, M. Haukka, G.I. Amanullayeva, K.T. Mahmudov and A.J.L. Pombeiro, Aquasoluble iron(III)-arylhydrazone-diketone complexes: Structure and catalytic activity for the peroxidative oxidation of C5-C8 cycloalkanes, J Inorg Biochem 115 (2012) 72.
106. W. Zuo, C. Tourbillon, V. Rosa, K. Cheaib, M.M. Andrade, S. Dagorne and R. Welter, Synthesis, crystal structures and use in ethylene oligomerization catalysis of novel mono-and dinuclear nickel complexes supported by (E)-N-(1-(thiophen-2-yl)ethylidene)benzohydrazide ligand, Inorg Chim Acta 383 (2012) 213.
107. M. Katyal and Y. Dutt, Analytical applications of hydrazones, Talanta 22 (1975), 151.
108. M.A. Kabil, S.E. Ghazy, M.A. Mostafa and A.A. El-Asmy, Micro-determination of Gold Using N-cyanoacylacetaldhyde hydrazone, Fresenivs J Anal Chem 349 (1994), 775.
109. A.A. Salem, Spectrophotometric and Potentiometric Characterization of Some Arylhydrazone Derivatives and their Applications in Lanthanide Determination, Microchem J 60 (1998), 51.
110. R. Dass and J.R. Mehta, A selective and rapid microdetermination of molybdeum(IV) using 2,4-dihydroxyacetophenone benzoylhydrazone as a new reagent, Indian J Chem 33 (1994), 438.
111. D. Vijayakumari and K. Lakshminarayana, A Brief review on Hydrazones as analytical reagents, J Radioanal Nucl Chem Lett 175 (1993), 1.
112. C. Ramachandraiah, D. Vijayakumari and K. Lakshminarayana, Sensitive spectrophotometric method for the determination of trace amouts of uranium(VI) using o-hydroxypropiophenoe isoicotinyl hydrazone, J Radioanal Nucl Chem Lett 175 (1993), 185.
113. M.G. Vargas, S. Trevilla and M. Milla, Synthesis and characterization of 1,2-cyclohexanedione bis-benzoyl-hydrazone and its application to the determination of Ti in minerals and rocks, Talanta 33 (1986), 209.
114. F. De Pablos, J.L.G. Ariza and F. Pino, Spectrophotometric Determination of Copper and Iron and Analysis of Their Mixtures by Means of Biacetyl (2-Pyridyl)hydrazone Thiosemicarbazone, Mikrochim Acta III (1985) 327.
115. T. Fujimolo, N. Teshima, M. Kurihara, S. Nakano and T. Kawashima, Catalytic determination of cobalt at sub-nanogram levels using the oxidative coupling of 3-methyl-2-benzothiazolinone hydrazone with N-ethyl-N-(2-hydroxy-3-sulfopropyl)-3,5-dimethoxyaniline by manual and flow-injection methods, Talanta 49 (1999), 1091.
116. T. Tomiyasu, N. Teshima, S. Nakano and T. Kawashima, Kinetic-catalytic determination of traces of iron by the oxidative coupling reaction of 3-methyl-2-benzothiazolinone hydrazone with N,N-dimethylaniline, Talanta 47 (1998), 1093.
117. M. Kaneko, M. Kurihara, S. Nakano and T. Kamashima, Flow-injection determination of chromium(III) by its catalysis on the oxidative coupling of 3-methyl-2-benzothiazolinone hydrazone with N-ethyl-N-(2-hydroxy-3-sulfopropyl)-3-methoxyaniline, Analytica Chim Acta 474 (2002), 167.
118. S. Sivaramaiah, P.R. Reddy,V.K. Reddy and T. Reddy, Direct and derivative spectrophotometric determination of thorium with 2,4-dihydroxybenzaldehyde isonicotinoyl hydrazone, J Radioanal Nucl Chem 245 (2000) 367.
119. S. Sivaramaiah and P.R. Reddy, Direct and derivative spectroscopic determination of Zinc with 2,4-Dihydroxybenzaldyde Isonicotonyl hydrazone in portable water and pharmaceutical samples, J Analy Chem 60 (2005), 828.
120. O. Babaiah, C.K. Rao, T.S. Reddy and V.K. Reddy, Rapid, selective, direct and derivative spectrophotometric determination of titanium with 2,4-dihydroxybenzaldeh-yde isonicotinoyl hydrazone, Talanta 43 (1996), 551.
121. S.H. Babu, K. Suvardhan, K.S.Kumar, K.M. Reddy,D. Rekha and P. Chiranjeevi, The facile flow-injection spectrophotometric detection of gold(III) inwater and pharmaceutical samples using3,5-dimethoxy-4-hydroxy-2-aminoacetophenone isonicontinoyl hydrazone (3,5-DMHAAINH), J Hazardous Material B120 (2005) 213.
122. S.A. Berger and D.E. Ryan, The use of substituted hydrazones as metallochromic indicators: The EDTA titration of copper, Mikrochim Acta (1974) 679.
123. P.C. Reddy and C.B. Rangamannar, Determination of iron and antimony by radiochemical displacement of60Co from cobalt-o-hydroxybenzaldehyde isonicotinoyl hydrazone, J Radioanal Nucl Chem Lett 165 (1992), 57.
124. N.Y. Sreedhar, V. Sivamoorthy, G.R. Reddy and B. Rangammanar, Determination of copper by a radiochemical displacement method, J Radioanal Nucl Chem Lett 119 (1987), 193.
125. T. Odashima, F. Anzai and H. Ishii, Substituted 2-thiophenealdehyde-2-benzothiazolyl-hydrazones as analytical reagents for copper, Anal Chim Acta 86 (1976), 231.
126. S.A. Berger, The Liquid-Liquid Extraction of Copper(II), Nickel(II), and Cobalt(II) with 2,2-Pyridil-mono-(2-quinolylhydrazone), Microchem J 47 (1993), 317.
127. S.A. Berger, Benzil-mono-(2-quinolyl)-hydrazone as a Chelating Agent for Copper, Mikrochim Acta I (1979), 311.
128. S.A. Berger, The solvent extraction of Cu(II), Ni(II) and Co(II) with benzil mono(2-quinolyl)hydrazone, Talanta 29 (1982), 718.
129. S.A. Berger, Diacetyl-bis-(2-pyridyl)hydrazone as an Extracting Agent for Cu(II), Co(II), and Ni(II), Mikrochim Acta III (1984), 275.
130. F. Gasparrini, D. Misiti, G. Natile and B. Galli, High-performance liquid chromatographic separations of some palladium( II) complexes with substituted hydrazones, J Chromatography 161 (1978), 356.
131. X. Ge, I. Wendler, P. Schramel and A. Kettrup, Application of polyacrolein-isonicotinic acid hydrazone resin for the separation and concentration of Pd and Pt in road dust, Reactive Functional Polymers 61 (2004) 1.
132. M.G. El-Meligy, S.E. El-Rafie and K.M. Abu-Zied, Preparation of dialdehyde cellulose hydrazone derivatives andevaluating their efficiency for sewage wastewater treatment, Desalination 173 (2005) 33.
133. Y.N. Ni, C. Liu and S. Koket, Simultaneous kinetic spectrophotometric determination of acetaminophen and phenobarbital by artificial neural networks and partial least squares, Anal Chim Acta 419 (2000) 185.
134. M. Sultan, Hydroxy-m-methoxy benzaldehyde) as analytical reagent in the analysis of pharmaceutical dosage forms, Il Farmaco 57 (2002) 865.
135. H.D. Revanasiddappa and B. Manju, Spectrophotometric determination of some antidepressant drugs using 3-methylbenzothiazolin-2-one hydrazone, Eur J Med Sci 9 (1999), 221.
136. N.A. El-Ragehy, S.S. Abbas and S.Z. El-khateeb, Stability indicating method for determination of nortriptyline hydrochloride using 3-methyl-2-benzothiazolinone hydrazone (MBTH), J Pharm Biomed Analy 25 (2001) 143.
137. A.A., El-Emam, F.F. Belal, M.A. Moustafa, S.M. El-Ashry, D.T. El-Sherbing and S.H. Hansen, Spectrophotometric determination of propranolol in formulations viaoxidative coupling with 3-methylbenzothiazoline-2-one hydrazone, Il Farmaco 58 (2003), 1179.
138. C.S.P. Sastry and D.M. Krishna, Spectrophotometric methods for the determination of labetalol hydrochloride in pure and dosage forms, Mikrochim Acta 122 (1996), 87.
139. C.S.P. Sastry, T.V. Rekha and A. Satyanarayana, Spectrophotometric determination of clozapine in pharmaceuticals, Mikrochim Acta 128 (1998), 201.
140. P.B. Issopoulos and P.T. Economou, Application of ternary complexes in pharmaceutical analysis, Fresenius J Anal Chem 345 (1993) 595.
141. P.B. Issopoulos and P.T. Economou, Spectrophotometric determination of iron(II) in anti-anaemic preparations using a newly developed Schiff's base, Fresenius J Anal Chem 342 (1992), 439.
142. C.S.R. Lakshmi and M.N. Reddy, Spectrophotometric estimation of nimesulide and its formulations, Mikrochim Acta 132 (1999), 1.