Cyclopalladated complexes containing tridentate thiosemicarbazone ligands of biological significance: Synthesis, structure and antimalarial activity

Chellan, Prinessa; Nasser, Shereen; Vivas, Livia; Chibale, Kelly; Smith, Gregory S.

doi:10.1016/j.jorganchem.2010.06.010

Cited by 97 publications

(53 citation statements)

References 66 publications

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“…As our interests lie also in the area of antiparasitic drugs [42,43] and since a few Pt(II) [44] and Pd(II) based complexes [45] with antimalarial activity (in the micromolar range) have been reported, we also tested the potential of the free ligands (1a-1c) and the complexes 2a-5c against the chloroquine-susceptible strain (3D7) and the chloroquine-resistant strain (W2) of Plasmodium falciparum.…”

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confidence: 99%

Platinum(II) and palladium(II) complexes with (N,N′) and (C,N,N′)− ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities

Quirante

Ruíz

González

et al. 2011

Journal of Inorganic Biochemistry

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The study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH 2 ) 2 NMe 2 }-3,5-R 2 -pzol] {where pzol represents pyrazole and R_H (1a), Me (1b) (5c)}. Compounds 4c and 5c arise from the orthometallation of the 3-phenyl ring of ligand 1c. Complex 2a has been further characterized by X-ray crystallography. Ligands and complexes were evaluated for their in vitro antimalarial against Plasmodium falciparum and cytotoxic activities against lung (A549) and breast (MDA MB231 and MCF7) cancer cellular lines. Complexes 2a-2c and 5c exhibited only moderate antimalarial activities against two P. falciparum strains (3D7 and W2). Interestingly, cytotoxicity assays revealed that the platinacycle 4c exhibits a higher toxicity than cisplatin in the three human cell lines and that the complex 2a presents a remarkable cytotoxicity and selectivity in lung (IC 50 = 3 μM) versus breast cancer cell lines (IC 50 N 20 μM). Thus, complexes 2c and 4c appear to be promising leads, creating a novel family of anticancer agents. Electrophoretic DNA migration studies in presence of the synthesized compounds have been performed, in order to get further insights into their mechanism of action.

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confidence: 99%

Platinum(II) and palladium(II) complexes with (N,N′) and (C,N,N′)− ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities

Quirante

Ruíz

González

et al. 2011

Journal of Inorganic Biochemistry

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“…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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“…Recently, there has been a great interest in thiosemicarbazones as potential antimalarial agents [14][15][16] . The pioneering work on acetylpyridine thiosemicarbazones 17 (VII) as antimalarials paved way for Pingaew et al 18 to develop benzoyl thiosemicarbazone analogues of isoquinoline (VIII) as antimalarials.…”

Section: Introductionmentioning

confidence: 99%

Novel pyrazole–pyrazoline hybrids endowed with thioamide as antimalarial agents: their synthesis and 3D-QSAR studies

Marella

Shaquiquzzaman

Akhter

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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One of the most viable options to tackle the growing resistance to the antimalarial drugs is hybrid molecules. It involves combination of different scaffolds in one frame that may lead to compounds with diverse biological profiles. In this context, new hybrids of three different scaffolds viz pyrazole, pyrazoline and thiosemicarbazone moiety were incorporated into one single compound and evaluated for their in vitro schizontocidal activity against the CQ-sensitive 3D7 strain of Plasmodium falciparum. Compounds with significant in vitro antimalarial activity were further evaluated for cytotoxicity against VERO cell lines. The best active compound 48 exhibited an IC 50 of 1.13 mM. The in vitro results were further validated by quantitative structure-activity relationship (QSAR).

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Cyclopalladated complexes containing tridentate thiosemicarbazone ligands of biological significance: Synthesis, structure and antimalarial activity

Cited by 97 publications

References 66 publications

Platinum(II) and palladium(II) complexes with (N,N′) and (C,N,N′)− ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities

Platinum(II) and palladium(II) complexes with (N,N′) and (C,N,N′)− ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities

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

Novel pyrazole–pyrazoline hybrids endowed with thioamide as antimalarial agents: their synthesis and 3D-QSAR studies

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