Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones

Mendes, Isolda C.; Moreira, Juliana P.; Mangrich, Antônio S.; Balena, Solange P.; Rodrigues, Bernardo L.; Beraldo, Heloísa

doi:10.1016/j.poly.2007.03.002

Cited by 94 publications

(27 citation statements)

References 22 publications

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“…The crystal structures of H2Ac4Ph [20] and H2Ac4mT [21] have been previously determined. Selected intra-molecular bond distances and angles for H2Ac4Ph [20], H2Ac4oT, H2Ac4mT [21], H2Ac4oClPh, H2Ac4mClPh and H2Ac4pClPh are given in Tables 2 and 3. As expected the distances and angles observed for the six thiosemicarbazones are comparable.…”

Section: Characterization Of the Thiosemicarbazonesmentioning

confidence: 99%

2-Acetylpyridine thiosemicarbazones: Cytotoxic activity in nanomolar doses against malignant gliomas

Lessa

Mendes

Silva

et al. 2010

European Journal of Medicinal Chemistry

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Section: Characterization Of the Thiosemicarbazonesmentioning

confidence: 99%

2-Acetylpyridine thiosemicarbazones: Cytotoxic activity in nanomolar doses against malignant gliomas

Lessa

Mendes

Silva

et al. 2010

European Journal of Medicinal Chemistry

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“…Elemental [16][17][18] , which was further confirmed by electronic spectroscopic studies. In the optical absorption spectrum, the chelate gave two bands at 27310 and 28998cm ).…”

Section: Characterization Of Cu(ii) Chelatementioning

confidence: 57%

Chelating Competency and Electrochemical Response of a Heterocyclic Phenylhydrazone and its Copper Chelate

Raphael¹,

Kakkassery²,

Shaju³

et al. 2014

Orient J Chem

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Heterocyclic compound 3-acetylpyridine phenylhydrazone (APPH) and its copper chelate were synthesized and characterized by spectral, elemental, magnetic and conductance measurements. Investigations showed that APPH behaved as bidentate ligand during chelation. The square planar geometry of the chelate was confirmed by magnetic and optical spectral studies. The detailed electrochemical response of the ligand and chelate were evaluated and reported.

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“…[42] For example, copper(II) halides (Cl/Br) with neutral thiosemicarbazones involved the deprotonation of the -N 2 H moiety to form copper(II) complexes (Scheme 4), as represented in Equation (1). The resulting complexes have anionic thiosemicarbazone ligands and are either four-coordinate square-planar {Cu II X(NNS)} complexes (Scheme 4, structure IV), [24,26,36,38,[42][43][44][45][46][47] or five-coordinate square-pyramidal complexes with bridging halogen or sulfur atoms and {Cu II X(μ-S) 2 NN} (Scheme 4, structure V) [24] and {Cu II (μ-X) 2 NNS} (Scheme 4, structure VI; X = Cl or Br in IV-VI) coordination cores. [45] On the other hand, the reactions of thiosemicarbazones with copper(I) …”

Section: Uniqueness In the Synthesis Of Copper(ii) Halide Complexes Amentioning

confidence: 99%

Stabilization of Cu^II–I Bonds Using 2‐Benzoylpyridine Thiosemicarbazones – Synthesis, Structure, Spectroscopy, Fluorescence, and Cyclic Voltammetry

et al. 2015

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The reactions of copper(I) iodide with N1‐substituted 2‐benzoylpyridine thiosemicarbazones [(C6H5)(C5H4N)C2=N3–N2H–C(=S)–N1HR (R = Me, HLMe; Et, HLEt; Ph, HLPh)] in acetonitrile/dichloromethane mixtures have formed the complexes [Cu2III2(μ4‐N,N,S‐LMe)2] (1), [CuIII(κ3‐N,N,S‐LEt)] (4), and [CuIII(κ3‐N,N,S‐LPh)] (7) through proton‐coupled electron transfer (PCET), and these complexes have rare CuII–I bonds. The above thio ligands with copper(I) bromide and copper(I) chloride also formed similar CuII–Br and CuII–Cl bonds in complexes of stoichiometry [CuIIX(κ3‐N,N,S‐L)] (L = LMe, LEt, LPh, X = Br 2, 5, 8; X = Cl 3, 6, 9) by PCET. All of the complexes have been characterized by elemental analysis, infrared spectroscopy, electronic absorption spectroscopy, ESR spectroscopy, magnetic susceptibility measurements, molecular fluorescence, cyclic voltammetry, and single‐crystal X‐ray crystallography. The thio ligands coordinate as monoanionic N,N,S donors in 1–9. The ESR data support the divalent oxidation state of the metal centers in the complexes, and the ESR parameters follow the trend g∥ > g⟂ > 2 with G values in the range 2–4, which suggests a d italicx 2–italicy 2 ground state for the copper(II) complexes with variable exchange interaction in the solid complexes. The geometry around each copper(II) center is distorted square planar (mononuclear, 2–9) or square pyramidal (dinuclear, 1). The stabilization of copper(II)–iodide bonds as well as the formation of CuII–Br and CuII–Cl bonds from thio ligands and copper(I) halides by a PCET process represents basic research of topical interest.

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Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones

Cited by 94 publications

References 22 publications

2-Acetylpyridine thiosemicarbazones: Cytotoxic activity in nanomolar doses against malignant gliomas

2-Acetylpyridine thiosemicarbazones: Cytotoxic activity in nanomolar doses against malignant gliomas

Chelating Competency and Electrochemical Response of a Heterocyclic Phenylhydrazone and its Copper Chelate

Stabilization of Cu^II–I Bonds Using 2‐Benzoylpyridine Thiosemicarbazones – Synthesis, Structure, Spectroscopy, Fluorescence, and Cyclic Voltammetry

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Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones

Cited by 94 publications

References 22 publications

2-Acetylpyridine thiosemicarbazones: Cytotoxic activity in nanomolar doses against malignant gliomas

2-Acetylpyridine thiosemicarbazones: Cytotoxic activity in nanomolar doses against malignant gliomas

Chelating Competency and Electrochemical Response of a Heterocyclic Phenylhydrazone and its Copper Chelate

Stabilization of CuII–I Bonds Using 2‐Benzoylpyridine Thiosemicarbazones – Synthesis, Structure, Spectroscopy, Fluo­rescence, and Cyclic Voltammetry

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Stabilization of Cu^II–I Bonds Using 2‐Benzoylpyridine Thiosemicarbazones – Synthesis, Structure, Spectroscopy, Fluorescence, and Cyclic Voltammetry