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-pyridinecarbaldehydethiosemicarbazone and sac=the saccharinate anion]

Ali, Mohammad Akbar; Mirza, Aminul Huq; Ravoof, Thahira Begum S. A.; Bernhardt, Paul V.

doi:10.1016/j.poly.2004.05.007

Cited by 43 publications

(2 citation statements)

References 24 publications

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“…Ligand hydroxylation of this kind is unusual but not without precedent. Our previous work has uncovered other Schiff base ligands derived from 2-pyridinecarbaldehyde which undergo Fe III catalysed oxidation reactions 34,54 leading to hydrazine (as opposed to hydrazone) analogues (the H 2 IPH analogues, Chart 1). The mechanism of this reaction is very complicated, 39 but nucleophilic attack by water on the C6vN2 double bond followed by ligand dehydrogenation are involved.…”

Section: Fe Complexationmentioning

confidence: 99%

“…The ligands share the same NNS, tridentate donor set as the HDp44mT and HPKTBH analogues, but the terminal substituent is a mercaptomethyl or mercaptobenzyl group rather than an amine or aromatic ring. Dithiocarbazate Schiff bases are well described and a number of transition metal complexes are known [31][32][33][34][35][36][37][38][39][40][41] and these compounds have shown a wide spectrum of biological activity. Little is known about the Fe coordination chemistry of these dithiocarbazate Schiff base ligands 42,43 and given the resemblance to the highly active thiosemicarbazone Fe chelators we have studied previously, 21,[28][29][30] this was the focus of the current work.…”

Section: Introductionmentioning

confidence: 99%

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Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity

et al. 2012

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The iron coordination and biological chemistry of a series of heterocyclic dithiocarbazate Schiff base ligands is reported with regard to their activity as Fe chelators for the treatment of Fe overload and also cancer. The ligands are analogous to tridentate heterocyclic hydrazone and thiosemicarbazone chelators we have studied previously which bear NNO and NNS donor sets. The dithiocarbazate Schiff base ligands in this work also are NNS chelators and form stable low spin ferric and ferrous complexes and both have been isolated. In addition an unusual hydroxylated ligand derivative has been identified via an Fe-induced oxidation reaction. X-ray crystallographic and spectroscopic characterisation of these complexes has been carried out and also the electrochemical properties have been investigated. All Fe complexes exhibit totally reversible Fe(III/II) couples in mixed aqueous solvents at potentials higher than found in analogous thiosemicarbazone Fe complexes. The ability of the dithiocarbazate Schiff base ligands to mobilise Fe from cells and also to prevent Fe uptake from transferrin was examined and all ligands were effective in chelating intracellular Fe relative to known controls such as the clinically important Fe chelator desferrioxamine. The Schiff base ligands derived from 2-pyridinecarbaldehyde were non-toxic to SK-N-MC neuroepithelioma (cancer) cells but those derived from the ketones 2-acetylpyridine and di-2-pyridyl ketone exhibited significant antiproliferative activity.

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Section: Fe Complexationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity

et al. 2012

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Tin(IV) Complexes with Thiosemicarbazide and 4‐Methyl‐3‐thiosemicarbazide Derivatives

Calatayud

López‐Torres

Mendiola

et al. 2007

Zeitschrift anorg allge chemie

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Synthesis and Spectroscopic Characterization of the Benzaldehyde Schiff Base of S‐Allyldithiocarbazate and its Copper(II) Complex and the X‐ray Crystal Structure of Bis[S‐allyl‐β‐N‐benzylidene)dithiocarbazato]Copper(II)

Yazdanbakhsh

Heravi

Takjoo

et al. 2008

Zeitschrift anorg allge chemie

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S-allyl-β-N-(benzylidene)dithiocarbazate (sabdtc, 1), prepared from hydrazine hydrate, carbon disulfide, allyl bromide and benzaldehyde, reacts with copper(II) nitrate in ethanol solution to form the complex Cu(sabdtc) 2 (2). 1 function as a single negatively charged bidentate chelating ligand and coordinates via the azomethine nitrogen atom and thioenolate sulfur atom to the metal ion. 1 and 2 were characterized by elemental analyses, 1 H NMR, 13 C NMR, UV/Vis, IR, and mass spectra. Spectroscopic evidences

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Cited by 43 publications

References 24 publications

Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity

Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity

Tin(IV) Complexes with Thiosemicarbazide and 4‐Methyl‐3‐thiosemicarbazide Derivatives

Synthesis and Spectroscopic Characterization of the Benzaldehyde Schiff Base of S‐Allyldithiocarbazate and its Copper(II) Complex and the X‐ray Crystal Structure of Bis[S‐allyl‐β‐N‐benzylidene)dithiocarbazato]Copper(II)

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