Unusual saccharin-N,O (carbonyl) coordination in mixed-ligand copper(II) complexes: Synthesis, X-ray crystallography and biological activity

[1]  I. Bruno,et al.  Cambridge Structural Database , 2002 .

[2]  E. Tiekink,et al.  Synthesis, characterization and biological studies of S-4-methylbenzyl-β-N-(2-furylmethylene)dithiocarbazate (S4MFuH) its Zn2+, Cu2+, Cd2+ and Ni2+ complexes , 2015 .

[3]  T. Junk,et al.  Synthesis, structure and magnetic characterization of dinuclear copper(II) complexes bridged by bicompartmental phenolate , 2015 .

[4]  Mohamed Ibrahim Mohamed Tahir,et al.  Synthesis, Characterization and Biological Evaluation of Transition Metal Complexes Derived from N, S Bidentate Ligands , 2015, International journal of molecular sciences.

[5]  G. Sheldrick.  Crystal structure refinement with SHELXL , 2015, Acta crystallographica. Section C, Structural chemistry.

[6]  E. Tiekink,et al.  Mixed-ligand metal complexes containing an ONS Schiff base and imidazole/benzimidazole ligands: synthesis, characterization, crystallography and biological activity , 2014, Transition Metal Chemistry.

[7]  Z. Trávníček,et al.  In vitro cytotoxicity, DNA cleavage and SOD-mimic activity of copper(II) mixed-ligand quinolinonato complexes. , 2012, Journal of inorganic biochemistry.

[8]  Louis J. Farrugia,et al.  WinGX and ORTEP for Windows: an update , 2012 .

[9]  F. Sonmez,et al.  New saccharin derivatives as tyrosinase inhibitors. , 2012, Bioorganic & medicinal chemistry.

[10]  M. Leskelä,et al.  A facile synthesis of mixed ligand Cu(II) complexes with salicylaldehyde and salicylaldimine ligands and their X-ray structural characterization , 2012 .

[11]  Á. Mombrú,et al.  Synthesis and Characterization of Heteroleptic Copper and Zinc Complexes with Saccharinate and Aminoacids. Evaluation of SOD-like Activity of the Copper Complexes , 2011, Biological Trace Element Research.

[12]  S. Franzblau,et al.  Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity. , 2010, European journal of medicinal chemistry.

[13]  Claudiu T Supuran,et al.  Carbonic anhydrase inhibitors. , 2003, Bioorganic & medicinal chemistry letters.

[14]  J. Ellena,et al.  Palladium(II) complexes with thiosemicarbazones: syntheses, characterization and cytotoxicity against breast cancer cells and Anti-Mycobacterium tuberculosis activity , 2010 .

[15]  K. Murray,et al.  Magnetic, spectroscopic and X-ray crystallographic structural studies on copper(II) complexes of tridentate NNS Schiff base ligands formed from 2-acetylpyrazine and S-methyl- and S-benzyldithiocarbazates , 2009 .

[16]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[17]  D. Richardson,et al.  Tuning the antiproliferative activity of biologically active iron chelators: characterization of the coordination chemistry and biological efficacy of 2-acetylpyridine and 2-benzoylpyridine hydrazone ligands , 2007, JBIC Journal of Biological Inorganic Chemistry.

[18]  K. Crouse,et al.  Synthesis, characterization and bioactivity of mixed-ligand Cu(II) complexes containing Schiff bases derived from S-benzyldithiocarbazate and saccharinate ligand and the X-ray crystal structure of the copper-saccharinate complex containing S-benzyl-β-N-(acetylpyrid-2-yl)methylenedithiocarbazate , 2007 .

[19]  V. Yilmaz,et al.  Metal complexes of saccharin , 2006 .

[20]  P. Naumov,et al.  Thermally Induced Saccharinate Ligand Flips Close to Ambient Temperature , 2006 .

[21]  R. Butcher,et al.  Synthetic, EPR spectroscopic, magnetic and x-ray crystallographic structural studies on copper(II) complexes of the tridentate N2S donor ligand formed from 6-methyl-2-formylpyridine and S-methyldithiocarbazate (Hmpsme) , 2005 .

[22]  E. Baran.  The saccharinate anion: a versatile and fascinating ligand in coordination chemistry , 2005 .

[23]  K. Crouse,et al.  Synthesis, characterization and bioactivity of mixed-ligand Cu(II) complexes containing S -methyldithiocarbazate derivatives and saccharinate ligands and the X-ray crystal structure of the copper–saccharinate complex containing S -methyl-β- N -(6-methylpyrid-2-yl)methylenedithiocarbazate , 2004 .

[24]  P. Bernhardt,et al.  Synthetic, spectroscopic and X-ray crystallographic structural study of the monomeric [Cu(pysme)(sac)(MeOH)] and dimeric [Cu(6mptsc)(sac)]2 complexes [pysme=anion of the pyridine-2-carboxaldehyde Schiff base of S-methyldithiocarbazate, 6mptsc=the anion of the 6-methyl-2-pyridinecarbaldehydethiosemic , 2004 .

[25]  M. Cordeiro,et al.  Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids. , 2004, Bioorganic & medicinal chemistry.

[26]  Anthony L. Spek,et al.  Journal of , 1993 .

[27]  R. Butcher,et al.  Mono- and bis-chelated nickel(II) complexes of the di-2-pyridylketone Schiff base of S -methyldithiocarbazate and the X-ray crystal structure of the bis[ S -methyl-β- N -(di-2-pyridyl)-methylenedithiocarbazato]nickel(II) complex , 2001 .

[28]  A. Ali,et al.  Synthesis and characterization of Zn(II) and Cd(II) complexes of S-benzyl-β-N-(2-pyridyl)methylenedithiocarbazate (HNNS): Bioactivity of the HNNS schiff base and its Zn(II), Cu(II) and Cd(II) complexes and the X-ray structure of the [Zn(NNS)2] complex , 2001 .

[29]  L. Falvello,et al.  Saccharinate as a versatile polyfunctional ligand. Four distinct coordination modes, misdirected valence, and a dominant aggregate structure from a single reaction system. , 2001, Inorganic chemistry.

[30]  K. Crouse,et al.  Complexes of a tridentate ONS Schiff base. Synthesis and biological properties , 2000 .

[31]  C. Maichle‐Mössmer,et al.  Synthesis, characterization and antifungal activity of group 12 metal complexes of 2-acetylpyridine-4N-ethylthiosemicarbazone (H4EL) and 2-acetylpyridine-N-oxide-4N-ethylthiosemicarbazone (H4ELO) , 1999 .

[32]  J. Bryan,et al.  Synthetic, spectroscopic and X-ray crystallographic structural studies on some copper(II) complexes of the 6-methylpyridine-2-carboxaldehyde Schiff base of S-methyldithiocarbazate , 1999 .

[33]  R. Butcher,et al.  The preparation and characterization of bis-chelated nickel(II) complexes of the 6-methylpyridine-2-carboxaldehyde Schiff bases of S-alkyldithiocarbazates and the X-ray crystal structure of the bis {S-methyl-β-N- (6-methylpyrid-2-yl)- methylenedithiocarbazato}nickel(II) complex , 1997 .

[34]  F. Smith,et al.  The synthesis, characterization and bioactivities of some copper(II) complexes of the 2-acetylpyridine schiff bases of s-methyl- and s-benzyldithiocarbazate, and the x-ray crystal structure of the nitrato(s-benzyl-β-n-(2-acetylpyridyl) methylenedithiocarbazato)copper(II) complex , 1996 .

[35]  J. Begum,et al.  Synthesis, characterization and biological activities of some nickel(II) complexes of tridentate NNS ligands formed by condensation of 2-acetyl-and 2-benzoylpyridines with S-alkyldithiocarbazates , 1993 .

[36]  S. Martelli,et al.  Synthesis, antibacterial and antifungal activity of metal (II) complexes of 2-acetylpyridine thiosemicarbazones. , 1993, Farmaco.

[37]  Wenbin Lin,et al.  Structure of a copper complex containing saccharin and imidazole : [Cu2(C6H4COSO2N)4(C3H4N2)4] , 1991 .

[38]  J. Waters,et al.  Preparation and characterization of complexes of the antitumour copper(II) 2-formylpyridine thiosemicarbazone (HL) system and the single-crystal X-ray structures of [{Cu(HL)(CF3CO2)}2][CF3CO2]2 and [Cu(HL)(H2O)(CLO4)2]·2H2O , 1991 .

[39]  E. Baker,et al.  The characterization of both the coordinated and non-coordinated saccharinate ion. The syntheses and crystal structures of aqua(2-formylpyridine thiosemicarbazonato)(saccharinato-N)copper(II) hemihydrate and 2,2′-bipyridyl-(2-formylpyridine thiosemicarbazonato)copper(II) saccharinate dihydrate , 1990 .

[40]  D. Dexter,et al.  Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization. , 1990, Journal of medicinal chemistry.

[41]  Nicholas Farrell,et al.  Transition Metal Complexes as Drugs and Chemotherapeutic Agents , 1989 .

[42]  P. Sharma,et al.  Metal(II) chelates of 4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone: Their preparation, characterization and antitumour activity , 1985 .

[43]  F. Cotton,et al.  Comparative study of structures, including Jahn-Teller effects, in the saccharinate complexes, [M(C7H4NO3S)2(H2O)4]•2H2O, of chromium and zinc, as well as other divalent metal ions , 1984 .

[44]  J. Rijn,et al.  SYNTHESIS, STRUCTURE, AND SPECTROSCOPIC PROPERTIES OF COPPER(II) COMPOUNDS CONTAINING NITROGEN-SULFUR DONOR LIGANDS: THE CRYSTAL AND MOLECULAR STRUCTURE OF AQUA(1,7-BIS(N-METHYLBENZIMIDAZOL-2′-YL)-2,6-DITHIAHEPTANE)COPPER(II) PERCHLOR , 1984 .

[45]  A. W. Addison,et al.  Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II) perchlorate , 1984 .

[46]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[47]  M. Hursthouse,et al.  X‐RAY CRYSTAL STRUCTURES OF METAL‐SACCHARIN COMPLEXES OF GENERAL FORMULA (M(C7H4NO3S)2(H2O)4).2H2O, WHERE M = FE(II), CO(II), NI(II) AND CU(II) , 1983 .

[48]  M. Hursthouse,et al.  X-ray crystal structures of metalsaccharin complexes of general formula [M(C7H4NO3S)2(H2O)4]·2H2O, where M = Fe(II), Co(II), Ni(II) and Cu(II) , 1983 .

[49]  M. Ali,et al.  Metal complexes of sulphur and nitrogen-containing ligands: Complexes of s-benzyldithiocarbazate and a schiff base formed by its condensation with pyridine-2-carboxaldehyde , 1977 .

[50]  S. Livingstone,et al.  Metal complexes of sulphur-nitrogen chelating agents , 1974 .

[51]  E. S. Horning,et al.  Cancer of the Urinary Bladder Induced in Mice with Metabolites of Aromatic Amines and Tryptophan , 1957, British Journal of Cancer.