Monomeric/dimeric complexes of fac-[Re(CO)3]+ with benzoylthiourea derivatives

Schmitt, Bonell; Gerber, Thomas; Hosten, Eric C.; Betz, Richard

doi:10.1016/j.inoche.2012.08.008

Cited by 22 publications

(22 citation statements)

References 37 publications

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“…The reaction with HL 2 led to the dimeric complex [Re 2 (CO) 6 (L 2 ) 2 ], in which L 2 acts as a monoanionic bidentate with coordination via the C=O oxygen and the C=S sulfur atoms, as a bridge between the two rhenium(I) centers. [289] Neutral monodentate coordination is found preferably in 1-acyl-3-mono-substituted thioureas (H 2 L), since the C=O···N−H intramolecular hydrogen bond favors the coordination through the S donor atom to the metal ions. This coordination mode was already discussed in the review article by Koch [6] [53] resulting in discrete hexameric clusters displaying a Cu 6 S 6 core consisting of two Cu 3 S 3 chair-shaped rings linked by coordination of the deprotonated amide nitrogen atom to a copper atom in the adjacent ring, forming a paddlewheel structure.…”

Section: Metal Complexesmentioning

confidence: 99%

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Saeed

Flörke

Erben

2013

Journal of Sulfur Chemistry

186

118

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This review provides an overview of the chemistry, structure and potential applications of 1-(acyl/aroyl)-3-(mono-substituted) and 1-(acyl/aroyl)-3,3-(di-substituted) thioureas, with general formula R 1 C(O)N (1) HC(S)N (3) R 2 R 3 . In recent years, the title compounds have found extensive applications as ligands in coordination chemistry. The effect that nitrogen substituents exert on the intra-and intermolecular hydrogen-bonding interactions is discussed, including their role on the coordination properties displayed by these ligands. Novel applications of transition metal complexes bearing 1-(acyl/aroyl)-3-(mono-and di-substituted) thioureas are introduced. Biological aspects are also highlighted. As recently demonstrated, high-throughput screening assay and structure-activity analyses are feasible for this class of compounds. The chemical versatility of 1-(acyl)-3-(substituted) thiourea molecules and the derived metal complexes, together with the possibility of determining detailed structural properties, join biological applications in a promising interdisciplinary approach. The bibliography includes 382 references with emphasis on the literature appearing after 2007.

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Section: Metal Complexesmentioning

confidence: 99%

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Saeed

Flörke

Erben

2013

Journal of Sulfur Chemistry

186

118

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“…Acylthiourea derivatives are established compounds which have been known for more than a century, and their extensive variety of applications makes them interesting molecules . In coordination chemistry, the acylthioureas act as versatile ligands due to the presence of S,N,O donor atoms in their structures, which allows for several coordination modes with different metal centers: (1) O,S bonded to a metal (anionic-bidentate), (2) S bonded to a metal (neutral-monodentate), (3) N bonded to a metal (neutral-monodentate), (4) O,N,N bonded to a metal (anionic-bidentate), (5) O,S bonded to a metal and N bonded to a metal (anionic-briged), and (6) S,N bonded to a metal (anionic-bidentate) . The cytotoxicity in the different cell lines of acylthiourea complexes with Ni(II), Co(III), Pd(II), Pt(II), Ru(II), and Au(I) has demonstrated the potential for these compounds as anticancer agents. − …”

Section: Introductionmentioning

confidence: 99%

Selective Coordination Mode of Acylthiourea Ligands in Half-Sandwich Ru(II) Complexes and Their Cytotoxic Evaluation

et al. 2020

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In this study, half-sandwich Ru(II) complexes containing acylthiourea ligands of the general type [Ru(η 6 -p-cymene)(PPh 3 )-(S)Cl]PF 6 (1m−6m) and [Ru(η 6 -p-cymene)(PPh 3 )(S−O)]PF 6 (1b− 6b) where S/S−O = N',N'-disubstituted acylthiourea were synthesized and characterized (via elemental analyses, IR spectroscopy, 1 H NMR spectroscopy, 13 C{ 1 H} NMR spectroscopy, and X-ray diffractometry), and their cytotoxic activity was evaluated. The different coordination modes of the acylthiourea ligands, monodentately via S (1m−6m) and bidentately via S,O (1b−6b), to ruthenium were modulated from different synthetic routes. The cytotoxicity of the complexes was evaluated in five human cell lines (DU-145, A549, MDA-MB-231, MRC-5, and MCF-10A) by MTT assay. The IC 50 values for prostate cancer cells (2.89−7.47 μM) indicated that the complexes inhibited cell growth, but that they were less cytotoxic than cisplatin (2.00 μM). Unlike for breast cancer cells (IC 50 = 0.28−0.74 μM) and lung cancer cells (IC 50 = 0.51−1.83 μM), the complexes were notably more active than the reference drug, and a remarkable selectivity index ) was observed for breast cancer cells. Based on both the activity and selectivity, complexes 5b and 6b, as well as their respective analogous complexes in the monodentate coordination 5m and 6m, were chosen for further investigation in the MDA-MB-231 cell line. These complexes not only induced morphology changes but also were able to inhibit colony formation and migration. In addition, the complexes promoted cell cycle arrest at the sub-G 1 phase inducing apoptosis. Interaction studies by viscosity measurements, gel electrophoresis, and fluorescence spectroscopy indicated that the complexes interact with the DNA minor groove and exhibit an HSA binding affinity.

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“…However, the structural coordination chemistry of the HL benz ligands as well as of the related bis(thioureas) H 2 L meta or H 2 L para has mainly focused on metal ions that prefer square‐planar or pseudo‐planar coordination environments such as Ni 2+ , Pd 2+ ,, Pt 2+ ,, and Cu 2+ . Additionally, a few examples of tris complexes with M 3+ ions have been reported, and the coordination chemistry of rhenium and technetium with such ligands is relatively well explored . Despite the fact that aroylthioureas should possess a high affinity to thiophilic metal ions, surprisingly less is known about this area of their coordination chemistry.…”

Section: Introductionmentioning

confidence: 99%

Ag^I Metallacoronates and Hg^II Metallacryptates Derived from a Catechol‐Based Aroylbis(N,N‐diethylthiourea)

2018

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Reactions of mixtures between Ag(NO 3 ) and alkaline earth nitrates with the bifunctional ligand 2,2′-{1,2-phenylenebis[oxyacetyl(N,N-diethylthiourea)]}, H 2 L cat , give {2}-metallacoronates of the composition {M ⊂ [Ag 2 (L cat ) 2 ]} (M = Ca 2+ , Sr 2+ , or Ba 2+ ). The trinuclear assemblies show further aggregation in the solid state, where they establish dimeric or polymeric entities stabilized by weak Ag···N (amide) interactions. Discrete {2}-[a]

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Monomeric/dimeric complexes of fac-[Re(CO)3]+ with benzoylthiourea derivatives

Cited by 22 publications

References 37 publications

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Selective Coordination Mode of Acylthiourea Ligands in Half-Sandwich Ru(II) Complexes and Their Cytotoxic Evaluation

Ag^I Metallacoronates and Hg^II Metallacryptates Derived from a Catechol‐Based Aroylbis(N,N‐diethylthiourea)

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Monomeric/dimeric complexes of fac-[Re(CO)3]+ with benzoylthiourea derivatives

Cited by 22 publications

References 37 publications

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Selective Coordination Mode of Acylthiourea Ligands in Half-Sandwich Ru(II) Complexes and Their Cytotoxic Evaluation

AgI Metallacoronates and HgII Metallacryptates Derived from a Catechol‐Based Aroylbis(N,N‐diethylthiourea)

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Ag^I Metallacoronates and Hg^II Metallacryptates Derived from a Catechol‐Based Aroylbis(N,N‐diethylthiourea)