Online citations, reference lists, and bibliographies.
← Back to Search

Coordination Chemistry Of Pyrazine Derivatives Analogues Of PZA: Design, Synthesis, Characterization And Biological Activity

M. Ogryzek, Agnieszka Chylewska, A. Królicka, Rafał Banasiuk, K. Turecka, Dorota Lesiak, Dawid Nidzworski, M. Makowski
Published 2016 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Ru(III) complexes with pyrazine derivatives: 2,3-bis(2-pyridyl)pyrazine (DPP), pyrazine-2-amidoxime (PAOX), pyrazine-2-thiocarboxamide (PTCA) and 2-amino-5-bromo-3-(methylamino)pyrazine (ABMAP) have been prepared. Characterization of the compounds was acquired using UV-Vis and FT-IR spectroscopy, elemental analysis, conductivity and electrochemical measurements as well as thermogravimetric studies. The ligand field parameters, Δ0 (splitting parameter), B (Racah parameter of interelectronic repulsion) and β (nephelauxetic ratio) were calculated. The stabilities of the Ru(III) complexes have also been confirmed by spectrophotometric titration methods in acetonitrile and water solutions. The data showed that the examined compounds are stable both in solution and solid states, which was also confirmed by the values of their stability constants found. Moreover, the molecular structures of the complexes have been optimized using AM1 and PM3 methods and this supported octahedral geometry around the Ru(III) ion. The minimum inhibitory (MIC) and minimum bactericidal concentration (MBC) for synthesized complexes were studied against two Gram (+) bacteria, two Gram (−) bacteria and fungi – three reference strains of Candida albicans. The results show that [RuCl(PAOX)2(OH2)]Cl2 display antifungal activity.
This paper references
Recent developments in the field of tumor-inhibiting metal complexes.
M. Galanski (2003)
Studies on pyrazine derivatives. XLVII. Synthesis and antibacterial activity of novel pyrazine derivatives with amidoxime moiety.
K. Gobis (2006)
Combination of Silver Nanoparticles and Drosera binata Extract as a Possible Alternative for Antibiotic Treatment of Burn Wound Infections Caused by Resistant Staphylococcus aureus
M. Krychowiak (2014)
Novel 5,7-disubstituted 6-amino-5H-pyrrolo[3,2-b]pyrazine-2,3-dicarbonitriles, the promising protein kinase inhibitors with antiproliferative activity.
G. G. Dubinina (2006)
Synthesis, Spectral and Thermal Properties of Some Penta-Coordinated Complexes of Oxovanadium(IV) Derived from Thiosemicarbazones of 4-Aminoantipyrine
R. Agarwal (2004)
Recent developments in ruthenium anticancer drugs.
A. Levina (2009)
Synthesis, spectra, dioxygen affinity and antifungal activity of Ru(III) Schiff base complexes.
R. Ramesh (2003)
Stability constants of Ru(III), Rh(III), Pd(III), Os(VIII), Ir(III) and Pt(IV) chelates with O-coumaric acid
S. Tripathi (1973)
Synthesis, structural characterisation and solution chemistry of ruthenium(III) triazole-thiadiazine complexes.
M. Delferro (2009)
Antimycobacterial activity of a series of pyrazinoic acid esters.
M. Cynamon (1992)
Kahrović, DNA Binding Properties of Two Ruthenium(III) Complexes Containing Schiff Bases Derived from Salicylaldehyde: Spectroscopic and Electrochemical Evidence of CT DNA Intercalation, Croat
N. Ljubijankić (2013)
Applications of ESI-MS in drug discovery: interrogation of noncovalent complexes
S. Hofstadler (2006)
Structure activity relationship studies of imidazo[1,2-a]pyrazine derivatives against cancer cell lines.
Shailaja Myadaraboina (2010)
Spectroscopic, Thermal and Biological Studies on Some Trivalent Ruthenium and Rhodium NS Chelating Thiosemicarbazone Complexes
V. K. Sharma (2007)
A general method for the determination of the stoichiometry of unknown species in multicomponent systems from physicochemical measurements
J. Kostrowicki (1987)
Synthesis , structural characterisation and solution chemistry of ruthenium ( III ) 52024 | RSC Adv . , 2016 , 6 , 52009 – 52025 triazole - thiadiazine complexes
A. Zahirović Ljubijankić (2006)
Ruthenium complexes can target determinants of tumour malignancy.
A. Bergamo (2007)
Structural, electronic, vibrational and NMR spectral analyses of [Ru(OAc)(2cqn)2NO] (H2cqn=2-chloro-8-quinolinol) isomers.
J. Wang (2014)
Interaction of apo-transferrin with anticancer ruthenium complexes NAMI-A and its reduced form.
O. Mazuryk (2012)
Mixed-ligand Ru(II) complexes with 2,2'-bipyridine and tetradentate Schiff bases auxiliary ligands: Synthesis, physico-chemical study, DFT analysis, electrochemical and Na+ binding properties.
L. Mishra (2008)
Synthesis, characterization, and DNA binding properties of a series of Ru, Pt mixed-metal complexes.
R. Williams (2003)
Transition metal complexes of thiosemicarbazide and thiosemicarbazones
M. J. Campbell (1975)
Substituents effect on the spectral studies on rutheninum(III) complexes of 5(-4'-derivatives phenyldiazo)-3-phenyl-2-thioxo-4-thiazolidinone.
A. Z. El-Sonbati (2002)
Synthesis and structure of [(η(6)-p-cymene)Ru(2-anthracen-9-ylmethylene-N-ethylhydrazinecarbothioamide)Cl]Cl; biological evaluation, topoisomerase II inhibition and reaction with DNA and human serum albumin.
Floyd A. Beckford (2011)
The heterocyclic ruthenium(III) complex KP1019 (FFC14A) causes DNA damage and oxidative stress in colorectal tumor cells.
S. Kapitza (2005)
DNA Binding Properties of Two Ruthenium(III) Complexes Containing Schiff Bases Derived from Salicylaldehyde: Spectroscopic and Electrochemical Evidence of CT DNA Intercalation
N. Ljubijankić (2013)
Coordination mode and reactivity of nickel(II) with vitamin B6
Agnieszka Chylewska (2014)
Controlling the reactivity of ruthenium(II) arene complexes by tether ring-opening.
Ana M Pizarro (2010)
Studies on the electronic absorption spectra of some selected furan derivatives. Molecular orbital calculations.
R. Abu-Eittah (1984)
The Chemistry of Pyrazine and Its Derivatives. VI. The Synthesis of Carbinols Containing the Pyrazine Nucleus1
M. R. Kamal (1962)
Selective estrogen receptor modulators in the ruthenocene series. Synthesis and biological behavior.
Pascal Pigeon (2005)
A ruthenium-containing organometallic compound reduces tumor growth through induction of the endoplasmic reticulum stress gene CHOP.
Xiangjun Meng (2009)
The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients. Flavor and Extract Manufacturers Association.
T. Adams (2002)
Pharmacological control of lung metastases of solid tumours by a novel ruthenium complex
G. Sava (2004)
Synthesis, spectroscopic characterization, electrochemical behaviour and antibacterial activity of Ru(III) complexes of 2-[(4-N,N'-dimethylaminophenylimino)-methyl]-4-halophenol.
G. Puthilibai (2009)
Os(VIII), Ir(III) and Pt(IV) chelates with Ocoumaric acid
S C Tripathi (1973)
Attractive S⋯π and π-π interactions in the pyrazine-2-thiocarboxamide structure: Experimental and computational studies in the context of crystal engineering and microbiological properties
Agnieszka Chylewska (2016)
Studies on the interactions between human serum albumin and trans-indazolium (bisindazole) tetrachlororuthenate(III).
L. Trynda-Lemiesz (2000)
D. Chatterjee (2006)
Ruthenium(II) and Rhodium(I) Triphenylphosphine Complexes Containing Semicarbazones and Tbiosemicarbazones
V. Chinnusamy (1993)
Maltol-derived ruthenium-cymene complexes with tumor inhibiting properties: the impact of ligand-metal bond stability on anticancer activity in vitro.
W. Kandioller (2009)
Inhibition of mitochondrial calcium ion transport by an oxo-bridged dinuclear ruthenium ammine complex.
W. Ying (1991)
Determination of dissociation constants for coordination compounds of Cr(III) and Co(III) using potentiometric and spectrophotometric methods
Agnieszka Chylewska (2008)
Chemistry around imidazopyrazine and ibuprofen: discovery of novel fatty acid amide hydrolase (FAAH) inhibitors.
Frédéric De Wael (2010)
Synthesis and antimycobacterial evaluation of substituted pyrazinecarboxamides.
M. Doležal (2008)
Ruthenium Polyaminocarboxylate Complexes
D. Chatterjee (2006)
KP1019, A New Redox‐Active Anticancer Agent – Preclinical Development and Results of a Clinical Phase I Study in Tumor Patients
Christian G Hartinger (2008)
Complexes of the 4d- and 5d-Groups. II. Crystal Field and Electron Transfer Spectra of Ruthenium(II) and (III), Iridium(IV), and Platinum(IV).
C. Jørgensen (1956)
Transferrin receptor 2 is frequently expressed in human cancer cell lines.
A. Calzolari (2007)
[Studies of pyrazine derivatives. XXI. Synthesis and tuberculostatic activity of 4-aryl-1-pyrazinoylthiosemicarbazides and the products of their cyclization to 1,2,4-triazole-3-thione derivatives].
W. Rudnicka (1986)
Interaction of anticancer Ru(III) complexes with single stranded and duplex DNA model systems.
D. Musumeci (2015)
Synthetic, structural and antifungal studies of coordination compounds of Ru(III), Rh(III) and Ir(III) with tetradentate Schiff bases
V. Sharma (2006)
Ruthenium(III) chloride complex with a tridentate bis(arylimino)pyridine ligand: synthesis, spectra, X-ray structure, 9-ethylguanine binding pattern, and in vitro cytotoxicity.
Ariadna Garza-Ortiz (2008)
HyperChem version 8.0
N. L. Allinger (1977)
Substituent effects in the control of the oxidation-reduction properties of metal ions in complexes with macrocyclic ligands
Jerome A. Streeky (1980)
Synthesis and Spectral Investigations of Some Platinum Metals Ions Coordination Compounds of 4[N-(Furan-2'-carboxalidene)Amino]Antipyrine Thiosemicarbazone and 4[N-(3',4',5'-Trimethoxybenzalidene)Amino]Antipyrine Thiosemicarbazone
R. Agarwal (2005)
Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms
N. L. Allinger (1977)
Defining Fractional Inhibitory Concentration Index Cutoffs for Additive Interactions Based on Self-Drug Additive Combinations, Monte Carlo Simulation Analysis, and In Vitro-In Vivo Correlation Data for Antifungal Drug Combinations against Aspergillus fumigatus
J. Meletiadis (2009)
Spectrophotometric, potentiometric, and conductometric studies of binary complex formation between copper(II) and three forms of vitamin B6 in aqueous solutions
Agnieszka Chylewska (2015)
Activities of synthetic peptides against human pathogenic bacteria.
K. Bogucka (2004)
From bench to bedside--preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A).
Christian G Hartinger (2006)
An organometallic protein kinase inhibitor pharmacologically activates p53 and induces apoptosis in human melanoma cells.
K. S. Smalley (2007)
[Studies on pyrazine derivatives. XXII. Synthesis and tuberculostatic activity of the products of reactions of pyrazinyl-1,3,4-oxadiazol-2-thione with amines].
D. Pancechowska-Ksepko (1988)
A biomimetic model of the electron transfer between P680 and the TyrZ-His190 pair of PSII.
Fabien Lachaud (2005)
Ruthenium(III) Coordination to the Exocyclic Nitrogen of 9‐Methyladenine and Stabilisation of the Rare Imine Tautomer by Intramolecular Hydrogen Bonding
A. Velders (2001)
DNA Binding Properties of Two Ruthenium ( III ) Complexes Containing Schi ff Bases Derived from Salicylaldehyde : Spectroscopic and Electrochemical Evidence of CT DNA Intercalation , Croat
L. Rozza Musumeci (2013)
Candida and candidiasis: the cell wall as a potential molecular target for antifungal therapy.
D. Gozalbo (2004)
Inhibition of cancer cell growth by ruthenium(II) arene complexes.
R. Morris (2001)
Synthesis, structural and spectral studies of 5-methyl 2-furaldehyde thiosemicarbazone and its Co, Ni, Cu and Cd complexes
E. M. Jouad (2001)
Organometallic ruthenium-based antitumor compounds with novel modes of action
Wee Han Ang (2011)
Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites.
D. A. Jose (2004)

This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar