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

Halder, Sourav; Peng, Shie‐Ming; Lee, Gene‐Hsiang; Chatterjee, Tanmay; Mukherjee, Asama; Dutta, Sushanta; Sanyal, Utpal; Bhattacharya, Samaresh

doi:10.1039/b707448d

Cited by 82 publications

(52 citation statements)

References 64 publications

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“…The differences between the two values are within normal ranges and generally consistent with bond lengths and angles for similar types of compounds such as in compounds (4), (5) and (6).…”

Section: Density Functional Theory (Dft) Calculationssupporting

confidence: 54%

“…In compounds (4), (5) and (6), the numbering system of the published structures is translated to coincide with the new data in (1), (2) and (3). and Hartwig couplings [11].…”

Section: Numbering Of Structures In Crystal Structure Tablesmentioning

confidence: 99%

“…In compounds (4), (5) and (6), the numbering system of the published structures is translated to coincide with the new data in (1), (2) and (3). (1) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-H atoms; (B, C) The molecular packing of (1) In (1), C11H15N3O2S·H2O, one molecule and a water molecule crystallize in the asymmetric unit, while in (2), C12H17N3O2S, a single molecule is present.…”

Section: Numbering Of Structures In Crystal Structure Tablesmentioning

confidence: 99%

“…This class of ligands has been widely studied due to their interesting coordination chemistry, prompting several reviews [1][2][3][4]. Metal complexes with thiosemicarbazone ligands have been found to have biological activity including anti-malarial [5] and anti-cancer properties [6]. Studies have also looked at the ability of these complexes to bind DNA [7] and they have even been investigated as biological imaging agents [8].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Crystal Structural Investigations, and DFT Calculations of Novel Thiosemicarbazones

et al. 2016

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(7)˝, β = 92.413(6)˝, and γ = 90.654(7)˝. DFT B3LYP/6-31(G) geometry optimized molecular orbital calculations were also performed and frontier molecular orbitals of each compound are displayed. The correlations between the calculated molecular orbital energies (eV) for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound have been proposed. Additionally, similar correlations observed among three closely related compounds, (4), 2-[1-(2-hydroxy-4-methoxyphenyl)ethylidene]-N-methyl-hydrazinecarbothioamide, (5), 2-[1-(2-hydroxy-6-methoxyphenyl)ethylidene]-N-methyl-hydrazinecarbothioamide acetonitrile monosolvate and (6), 2-[1-(2-hydroxy-6-methoxyphenyl)ethylidene]-N-ethyl-hydrazinecarbothioamide, examining structural differences from the substitution of the methoxy group from the phenyl ring (4, 5, or 6 position) and the substitution of the terminal amine (methyl or ethyl) to their frontier molecular orbital surfaces and from their Density Functional Theory (DFT) molecular orbital energies provide further support for the suggested assignments of the title compounds.

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“…The differences between the two values are within normal ranges and generally consistent with bond lengths and angles for similar types of compounds such as in compounds (4), (5) and (6).…”

Section: Density Functional Theory (Dft) Calculationssupporting

confidence: 54%

“…In compounds (4), (5) and (6), the numbering system of the published structures is translated to coincide with the new data in (1), (2) and (3). and Hartwig couplings [11].…”

Section: Numbering Of Structures In Crystal Structure Tablesmentioning

confidence: 99%

Section: Numbering Of Structures In Crystal Structure Tablesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Crystal Structural Investigations, and DFT Calculations of Novel Thiosemicarbazones

et al. 2016

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“…In an attempt to prepare binuclear palladium dithiosemicarbazones, the palladium(II) complexes (7)(8)(9)(10)(11)(12) were selectively prepared by reacting the corresponding dithiosemicarbazone ligands (1-6) with Pd(PPh 3 ) 2 Cl 2 in a 1:2 stoichiometric ratio (ligand:metal), giving rise to binuclear palladium complexes (Scheme 2). The synthesis of the complexes was performed using methodologies similar to those reported previously by Halder et al [34].…”

Section: Binuclear Dithiosemicarbazone Salicylaldiminato Palladium(iimentioning

confidence: 99%

Synthesis and structural characterization of binuclear palladium(II) complexes of salicylaldimine dithiosemicarbazones

et al. 2009

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a b s t r a c tA series of binuclear palladium(II) salicylaldiminato dithiosemicarbazone complexes have been synthesized and characterized. The palladium complexes were obtained by the reaction of various ethyleneand phenylene-bridged dithiosemicarbazones with Pd(PPh 3 ) 2 Cl 2 . The free salicylaldimine ligands and their palladium complexes were characterized by NMR and IR spectroscopies, ESI-mass spectrometry, elemental analyses and for two representative complexes also by X-ray diffraction. In both metal complexes, the solid-state structures show the two palladium centers to be coordinated in a slightly distorted square-planar geometry, which gives rise in each case to five-and six-membered chelate rings. The salicylaldimine thiosemicarbazone ligands coordinate to palladium in a tridentate manner, through the phenolic oxygen, imine nitrogen and thiolate sulfur atoms.

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Thiosemicarbazone Salicylaldiminato‐Palladium(II)‐Catalyzed Mizoroki–Heck Reactions

et al. 2010

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PPh 3 ] [saltsc = salicylaldehyde thiosemicarbazone; R = H (1), 3-tert-butyl (2), 3-methoxy (3), 5-chloro (4)], have been evaluated as catalyst precursors for the Mizoroki-Heck coupling reaction between a variety of electron-rich and electron-poor aryl halides and olefins. The palladium complexes (0.1-1 mol% loading) were found to effectively catalyze these reactions with high yields being obtained when aryl iodides and aryl bromides were utilized. The effects of base, catalyst loading, reaction temperature and reaction time on the catalytic activity of the most active complex were also investigated.Keywords: aryl halides; low metal loading; methyl acrylate; Mizoroki-Heck coupling; palladium(II) complexesThe synthesis and study of thiosemicarbazones as biological agents has received copious attention over the past few decades.[1-8] These Schiff base-type compounds contain several donor atoms and research into the coordination chemistry and biological applications of their metal complexes is fast becoming an area of prominent interest. [9][10][11][12][13][14] Their palladium(II) and platinum(II) complexes have been studied as anticancer agents and show great promise as chemotherapeutic agents. [12,13] While studies into the biological application of thiosemicarbazone metal complexes is prolific there are few reports on their use in catalysis. One of the first reports of their catalytic application was published in 1998.[15] Pelagatti and co-workers described chemoselective homogeneous hydrogenation reactions using tridentate [N,N,S]thiosemicarbazone palladium(II) complexes. [15] Palladium-catalyzed reactions have become essential synthetic tools; their applications including the syntheses of polymers, [16,17] natural products, [18] agrochemicals [19,20] and pharmaceuticals. [21,22] There are several well-known reactions that utilize palladiumcontaining compounds including the Mizoroki-Heck, Stille, Suzuki and Buchwald-Hartwig cross-couplings. [23,24] As with most of these coupling reactions, the Mizoroki-Heck reaction requires a palladium(0) source as catalyst and this is usually generated in situ by reduction of a palladium(II) complex.[25] Salicylaldehyde thiosemicarbazone Pd(II) complexes were recently applied as catalyst precursors for the Heck reaction [26] and the Suzuki-Miyuara [27,28] coupling reaction and were shown to effectively catalyze carboncarbon bond formation.In our group, we are currently investigating the synthesis and application of tridentate thiosemicarbazone transition metal complexes. We have prepared a series of palladium(II) complexes containing functionalized salicylaldimine thiosemicarbazones and evaluated them for activity as anticancer and antimalarial agents.[29] These complexes have shown promising biological activity and as part of our continuing study into the versatility of thiosemicarbazone metal complexes we chose to screen these complexes as catalyst precursors for the Mizoroki-Heck coupling reaction.

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

Cited by 82 publications

References 64 publications

Synthesis, Crystal Structural Investigations, and DFT Calculations of Novel Thiosemicarbazones

Synthesis, Crystal Structural Investigations, and DFT Calculations of Novel Thiosemicarbazones

Synthesis and structural characterization of binuclear palladium(II) complexes of salicylaldimine dithiosemicarbazones

Thiosemicarbazone Salicylaldiminato‐Palladium(II)‐Catalyzed Mizoroki–Heck Reactions

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