Structural Studies of 2,6-Diacetyl- and 2,6-Diformylpyridine Bis(thiosemicarbazones)

Brown, Christine; Kaminsky, Werner; Claborn, Kacey; Goldberg, Karen I.; West, Douglas X.

doi:10.1590/s0103-50532002000100003

Cited by 24 publications

(4 citation statements)

References 36 publications

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“…Found: C 55.62; H 3.86; N 7.50%. 1 H NMR in CDCl 3 d/ppm: 4.76 (s, 2H), 6.62 (t, J = 7.3 Hz, 1H), 6.68 (d, J = 8.5 Hz, 1H), 7.22 (t, J = 7.7 Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.41-7.75 20 (PPh 3 ), 8.24 (d,J = 12.99 Hz,1H).…”

Section: Synthesismentioning

confidence: 99%

“…Found: C 42.38;H 3.45; N 14.23%. 1 H NMR in CDCl 3 d/ppm: 2.44 (s, 3H), 4.87 (s, 2H), 6.67 (t, J = 7.3 Hz, 1H), 7.03 (d,J = 8.8 Hz,1H),7.24 (d,J = 5.7 Hz, 2H), 7.29-7.34 20 (2H), 7.92 (s, 1H), 8.62 (d, J = 5.9 Hz, 2H).…”

Section: Synthesismentioning

confidence: 99%

“…Found: C 44.44;H 3.86;N 13.76%. 1 H NMR in CDCl 3 d/ppm: 2.43 (s, 3H), 2.75 (s, 3H), 4.84 (s, 2H), 6.68 (t, J = 7.3 Hz, 1H), 7.04 (d,J = 8.2 Hz,1H),7.68 (d,J = 8.2 Hz,1H),8.61 (d,J = 6.2 Hz,1H).…”

Section: Synthesismentioning

confidence: 99%

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Synthesis, structure, spectroscopic properties and cytotoxic effect of some thiosemicarbazone complexes of palladium

et al. 2008

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Reaction of salicylaldehyde thiosemicarbazone (H 2 L 1 ), 2-hydroxyacetophenone thiosemicarbazone (H 2 L 2 ) and 2-hydroxynaphthaldehyde thiosemicarbazone (H 2 L 3 ) (general abbreviation H 2 L, where H 2 stands for the two dissociable protons, one phenolic proton and one hydrazinic proton) with Na 2 [PdCl 4 ] affords a family of polymeric complexes of type [{Pd(L)} n ]. Reaction of the polymeric species with two monodentate ligands (D), viz. triphenylphosphine (PPh 3 ) and 4-picoline (pic), has yielded complexes of type [Pd(L)(D)]. These mixed-ligand complexes have also been obtained from reaction of the thiosemicarbazones with [Pd(PPh 3 ) 2 Cl 2 ] and [Pd(pic) 2 Cl 2 ]. Crystal structures of [Pd(L 1 )(PPh 3 )] and [Pd(L 2 )(pic)] have been determined. The [Pd(L)(D)] complexes show characteristic 1 H NMR spectra and intense absorptions in the visible and ultraviolet region. They also fluoresce in the visible region at ambient temperature. In vitro cytotoxicity screenings of the complexes along with four human clinical drugs viz. cisplatin, BCNU, 5-fluorouracil (5-FU) and hydroxyurea have been carried out in two human tumor cell lines, namely promyelocytic leukemia HL-60 and histiocytic lymphoma U-937. [Pd(L 2 )(PPh 3 )] shows the lowest IC 50 value and is found to be much more cytotoxic than the reference anticancer drugs in both the cell lines. An apoptosis study in HL-60 with [Pd(L 2 )(PPh 3 )] confirms that at 10 mM concentration it induces apoptosis to a greater extent than cisplatin and camptothecin.

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Section: Synthesismentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

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Synthesis, structure, spectroscopic properties and cytotoxic effect of some thiosemicarbazone complexes of palladium

et al. 2008

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“…The most numerous are those that act as tridentate and pentadentate ligands. [11][12][13][14] Some time ago, synthesis, spectroscopic and magnetic characterization of mono-and bis(ligand) complexes of Fe(II), Co(II), Ni(II) and Cu(II) with the tridentate N 3 ligand, 2,6-diacetylpyridine bis(phenylhydrazone) of general formulae [M(L)Cl 2 ] and [ML 2 ](ClO 4 ) 2 were described. 11 Recently, complexes with the title ligand, i.e., [CoL 2 ]I 2 15 and [CuL 2 ]Br 2 , 16 have been synthesized and structurally characterized, which represent the only metal complexes with this ligand to be characterized by SC-XRD so far.…”

Section: Introductionmentioning

confidence: 99%

Reactions of copper(II) bromide with 2,6-diacetylpyridine bis(phenyl-hydrazone) (L)-molecular and crystal structure of L and its mixed-valence complex [CuIIL2][CuI2Br4]

Rodić

Radanović

Gazdic

et al. 2022

JSCS

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Utilizing X-ray crystallography the crystal and molecular structures of 2,6-diacetylpyridine bis(phenylhydrazone) (L) were determined. Energetics of the intermolecular interactions in the crystal structure was assessed with computational methods, revealing that dispersion interactions are dominant. The basic structural unit of the crystal packing is revealed to be the herring-bone type arrangement of L molecules. Assignation of the IR spectrum of L with the aid of DFT calculations was performed. Furthermore, new reactions of L with CuBr2 in different solvents are described, which led to the synthesis of the mixed Cu(II)-Cu(I) complex of the formula [CuIIL2][CuI2Br4] (1), and its structural characterization. In the complex cation, two molecules of tridentate N3 ligand are meridionally arranged in a very distorted octahedral environment of a Cu(II) ion. In [Cu2Br4]2-, bromide ions are arranged in a trigonal-planar geometry around each copper(I) atom. Finally, for the ligand, 1, and the previously synthesized complex [CuL2]Br2, thermal properties were examined. The thermal stability of the com-plexes is lower than that of the ligand and decreases in order: L (250?C) > > [CuL2]Br2 (221?C) > [CuIIL2][CuI2Br4] (212?C). The differences in thermal stability of the complexes are due to differences in packing efficacy of the constitutional ions.

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Lanthanide(III) Complexes of Bis‐semicarbazone and Bis‐imine‐Substituted Phenanthroline Ligands: Solid‐State Structures, Photophysical Properties, and Anion Sensing

Nadella

Paulraj

Suresh

et al. 2012

Chemistry A European J

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Phenanthroline-based hexadentate ligands L(1) and L(2) bearing two achiral semicarbazone or two chiral imine moieties as well as the respective mononuclear complexes incorporating various lanthanide ions, such as La(III), Eu(III), Tb(III), Lu(III), and Y(III) metal ions, were synthesized, and the crystal structures of [ML(1)Cl(3)] (M=La(III), Eu(III), Tb(III), Lu(III), or Y(III)) complexes were determined. Solvent or water molecules act as coligands for the rare-earth metals in addition to halide anions. The big Ln(III) ion exhibits a coordination number (CN) of 10, whereas the corresponding Eu(III), Tb(III), Lu(III), and Y(III) centers with smaller ionic radii show CN=9. Complexes of L(2), namely [ML(2)Cl(3)] (M=Eu(III), Tb(III), Lu(III), or Y(III)) ions could also be prepared. Only the complex of Eu(III) showed red luminescence, whereas all the others were nonluminescent. The emission properties of the Eu derivative can be applied as a photophysical signal for sensing various anions. The addition of phosphate anions leads to a unique change in the luminescence behavior. As a case study, the quenching behavior of adenosine-5'-triphosphate (ATP) was investigated at physiological pH value in an aqueous solvent. A specificity of the sensor for ATP relative to adenosine-5'-diphosphate (ADP) and adenosine-5'-monophosphate (AMP) was found. (31)P NMR spectroscopic studies revealed the formation of a [EuL(2)(ATP)] coordination species.

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Structural Studies of 2,6-Diacetyl- and 2,6-Diformylpyridine Bis(thiosemicarbazones)

Cited by 24 publications

References 36 publications

Synthesis, structure, spectroscopic properties and cytotoxic effect of some thiosemicarbazone complexes of palladium

Synthesis, structure, spectroscopic properties and cytotoxic effect of some thiosemicarbazone complexes of palladium

Reactions of copper(II) bromide with 2,6-diacetylpyridine bis(phenyl-hydrazone) (L)-molecular and crystal structure of L and its mixed-valence complex [CuIIL2][CuI2Br4]

Lanthanide(III) Complexes of Bis‐semicarbazone and Bis‐imine‐Substituted Phenanthroline Ligands: Solid‐State Structures, Photophysical Properties, and Anion Sensing

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