Biological studies of newly synthesized ferrocenyl complexes containing triazinone moiety

A new ferrocenyl ligand, 1,1′-bis[1-methyl-5-phenyl-4H-(1,3,4)-thiadiazolo(2,3-c)(1,2,4)triazin-4-one]ferrocene was prepared from the reaction of 1,1′-diacetylferrocene with 4-amino-2,3-dihydro-6-phenyl-3-thioxo[1,2,4]triazin-5(4H)one. The ligand, L, forms 1:1 complexes with Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) in good yield. Characterization of the ligand and its complexes was carried out using IR, 1H NMR, magnetic susceptibility as well as elemental analysis. Biological activity of the ligand and its complexes were carried out against Aspergillus niger, Cladosporium herbirum and Fusarium moniliformae using filter paper discs; and against bacterial strains of Escherichia coli, Staphylococcus aureus using viable cell counting technique. The results indicated that the ligand is biologically active whereas the complexes are more active than the ligand. Copyright © 2006 John Wiley & Sons, Ltd.

[1]  I. Ali,et al.  Preparation, characterization and biological studies of some novel ferrocenyl compounds , 2006 .

[2]  W. Hegazy,et al.  Synthesis, characterization and biological studies of ferrocenyl complexes containing thiophene moiety , 2005 .

[3]  Jianxin Fang,et al.  Synthesis, structures and biological activity research of novel ferrocenyl-containing 1H-1,2,4-triazole derivatives , 2005 .

[4]  A. Csámpai,et al.  Synthesis, NMR, IR spectroscopic and X-ray study of novel [pyridazin-3(2H)-one-6-yl]ferrocenes and related ferrocenophane derivatives. Study on ferrocenes. Part 14 , 2005 .

[5]  C. S. Allardyce,et al.  Development of organometallic (organo‐transition metal) pharmaceuticals , 2005 .

[6]  L. Böhm,et al.  223 Evaluation of 2 new Rhodium ferrocene complexes for cytotoxicity, and apoptotic propensity to invoke alternative cell death pathways in prostate tumour cell lines , 2004 .

[7]  Huilin Chen,et al.  Chiral ferrocene-based phosphine-imine and sulfur-imine ligands for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters , 2004 .

[8]  S. Buchwald,et al.  A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines , 2004 .

[9]  M. M. Abd-Elzaher.  Synthesis and Spectroscopic Characterization of Some Ferrocenyl Schiff Bases Containing Pyridine Moiety and Their Complexation with Cobalt, Nickel, Copper and Zinc , 2004 .

[10]  J. C. Garcia-Monteagudo,et al.  Complexes of dichloro[2-(dimethylaminomethyl)phenyl-C1,N]gold(III), [Au(damp-C1,N)Cl2], with formylferrocene thiosemicarbazones: synthesis, structure and cytotoxicity. , 2004, Journal of inorganic biochemistry.

[11]  M. M. Abd-Elzaher.  Synthesis, characterization, and antimicrobial activity of cobalt(II), nickel(II), copper(II) and zinc(II) complexes with ferrocenyl Schiff bases containing a phenol moiety , 2004 .

[12]  Min Zhang,et al.  First-principles study on second-order optical nonlinearity of some ferrocenyl complexes , 2004 .

[13]  Nigel J. Forrow,et al.  Transition metal half-sandwich complexes as redox mediators to glucose oxidase. , 2004, Biosensors & bioelectronics.

[14]  J. Cui,et al.  Synthesis, characterization and in vitro antitumor activity of some arylantimony ferrocenecarboxylates and crystal structures of C5H5FeC5H4CO2SbPh4 and (C5H5FeC5H4CO2)2Sb(4‐CH3C6H4)3 , 2003 .

[15]  A. Osowole,et al.  Synthesis and Physico‐Chemical Properties of Some Copper(II) β‐Ketoamines and Their Adducts with 2,2′‐Bipyridine and 1,10‐Phenanthroline , 2003 .

[16]  J. Raoof,et al.  Catalytic Oxidation of Sulfite by Ferrocenemonocarboxylic Acid at the Glassy Carbon Electrode. Application to the Catalytic Determination of Sulfite in Real Sample , 2002 .

[17]  T. Miyashita,et al.  Nonlinear optical properties of novel carborane???ferrocene conjugated dyads. Electron-withdrawing characteristics of carboranesElectronic supplementary information (ESI) available: a complete Experimental section containing HRS measurements, full NMR, IR, UV, mass spectrometry, and elemental analys , 2002 .

[18]  C. Supuran,et al.  SYNTHESIS AND CHARACTERIZATION OF ANTIBACTERIAL Co(II), Cu(II), Ni(II), AND Zn(II) COMPLEXES OF ACYLHYDRAZINE DERIVED PYRROLYL COMPOUNDS , 2002 .

[19]  A. Moyano,et al.  β-Ferrocenyl-β-amino alcohols: a new class of central chiral ferrocene derivatives , 2002 .

[20]  G. Leclercq,et al.  Studies on organometallic selective estrogen receptor modulators. (SERMs) Dual activity in the hydroxy-ferrocifen series , 2001 .

[21]  Z. Chohan,et al.  SYNTHESIS, CHARACTERIZATION, LIGATIONAL AND BIOLOGICAL PROPERTIES OF SOME ACYLHYDRAZINE DERIVED FURANYL AND THIENYL SCHIFF BASES WITH Co(II), Cu(II), Ni(II), AND Zn(II) METAL IONS , 2001 .

[22]  W. Henderson,et al.  Platinum(II) complexes containing ferrocene-derived phosphonate ligands; synthesis, structural characterisation and antitumour activity , 2001 .

[23]  Z. Chohan,et al.  Synthesis, characterization, coordination and antibacterial properties of novel asymmetric 1,1′-disubstituted ferrocene-derived Schiff-base ligands and their Co(II), Cu(II) Ni(II) and Zn(II) complexes , 2001 .

[24]  C. Biot,et al.  Synthetic ferrocenic mefloquine and quinine analoguesas potential antimalarial agents. , 2000, European journal of medicinal chemistry.

[25]  S. El-Sheikh,et al.  A One-Pot Synthesis of [1,2,4]Triazino[4,3-b]-[1,2,4,5]tetrazines , 2000 .

[26]  C. Biot,et al.  Synthesis and antimalarial activity in vitro of potential metabolites of ferrochloroquine and related compounds. , 1999, Bioorganic & medicinal chemistry.

[27]  M. Kidwai,et al.  Microwave Induced Synthesis of Ferrocenyl Substituted 1,2,4-s-Triazolo[3,4-b]-1,3,4-thiadiazoles , 1999 .

[28]  C. Biot,et al.  In Vitro Antimalarial Activity of a New Organometallic Analog, Ferrocene-Chloroquine , 1998, Antimicrobial Agents and Chemotherapy.

[29]  P. Beer,et al.  Tunable bis(ferrocenyl) receptors for the solution-phase electrochemical sensing of transition-metal cations , 1998 .

[30]  C. Biot,et al.  Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue. , 1997, Journal of medicinal chemistry.

[31]  James C. Chang,et al.  Synthesis and Characterization of Amino Acid Schiff Base Complexes of Nickel(II) , 1994 .

[32]  L. Yadav,et al.  Hetero Diels-Alder synthesis and fungitoxicity of new 1,3,4-thiadiazolo[3,2-a]-s-triazine-5(H)-thiones , 1994 .

[33]  L. Yadav,et al.  New fungitoxic fused-ring synthetics incorporating azoles and azines in different combinations , 1994 .

[34]  R. C. Pandey,et al.  Antifungal anthracycline antibiotics, spartanamicins A and B from Micromonospora spp. , 1992, The Journal of antibiotics.

[35]  J. Ehinmidu,et al.  Antifungal activity of n-tributyltin acetate against some common yam rot fungi , 1992, Applied and environmental microbiology.

[36]  F. Nan,et al.  Ferrocenyl thiosemicarbazone and its transition metal complexes , 1992 .

[37]  T. Maren,et al.  Synthesis and physicochemical properties of thiadiazolo[3,2-a]pyrimidinesulfonamides and thiadiazolo[3,2-a]triazinesulfonamides as candidates for topically effective carbonic anhydrase inhibitors. , 1987, Journal of medicinal chemistry.

[38]  M. Joho,et al.  The isolation and characterization of Ni2+ resistant mutants of Saccharomyces cerevisiae. , 1987, Microbios.

[39]  P. Greenfield,et al.  A review of yeast ionic nutrition. I: Growth and fermentation requirements , 1984 .

[40]  S. Patil,et al.  Some ferrocenyl aroyl hydrazones and their copper(II) complexes , 1982 .

[41]  R. Woodward,et al.  The Structure and Chemistry of Ferrocene. III. Evidence Pertaining to the Ring Rotational Barrier , 1958 .