ReVO and ReVNPh complexes with pentadentate benzamidines – Synthesis, structural characterization and DFT evaluation of isomeric complexes

Nguyen, Hung Huy; Pham, Chien Thang; Abram, Ulrich

doi:10.1016/j.poly.2015.07.079

Cited by 10 publications

(10 citation statements)

References 31 publications

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“…The ruthenium–ligand distances, namely C(55) ─ Ru(1) 1.863(10) Å, O(2) ─ Ru(1) 2.161(5) Å, N(1) ─ Ru(1) 2.166(7) Å, S(1) ─ Ru(1) 2.345(2) Å, P(2) ─ Ru(1) 2.402(19) Å, P(4) ─ Ru(1) 2.403(2) Å, found in 1 agree well with those reported for other similar ruthenium(II) complexes containing triphenylphosphine in trans position and the carbonyl group (CO) is trans to the nitrogen atom. The same phenomenon occurred with rhenium complexes in different oxidation states containing the same type of benzamidines …”

Section: Resultssupporting

confidence: 56%

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

Vijayan

Viswanathamurthi

Sugumar

et al. 2016

Applied Organom Chemis

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N,N-[(diethylamino)(thiocarbonyl)]-substituted benzamidine ligands have been synthesized from the reaction of N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride with functionalized amines such as 2-aminophenol and 2-picolylamine. The reaction of N,N-[(diethylamino)(thiocarbonyl)]-2-hydroxyphenylbenzamidine (H 2 L 1 ) with ruthenium(II) precursor [RuHCl(CO)(PPh 3 ) 3 ] afforded complex 1 of the type [Ru(L 1 )(CO)(PPh 3 ) 2 ] in which the ligand coordinated in tridentate ONS mode. The reaction of H 2 L 1 with copper precursor [Cu(CH 3 COO)(PPh 3 ) 2 ] induced C═N bond cleavage of the ligand and afforded complex 3 of the type [Cu(1,1-DT) (Cl)(PPh 3 ) 2 ] (1,1-DT = 1,1-diethylthiourea) in which the ligand coordinated in a monodentate fashion. The ligand N,N-[(diethylamino)(thiocarbonyl)]-2picolylbenzamidine (HL 2 ) reacted with ruthenium(II) and copper(I) precursors to form complex 2 of the type [Ru(1,1-DT)(Cl 2 )(CO)(PPh 3 ) 2 ] and complex 3, respectively, in which the ligand underwent C═N cleavage and coordinated in a monodentate fashion via C═S group. In complexes 1 and 2, the two triphenylphosphine co-ligands coordinated in trans position whereas, in complex 3, the two triphenylphosphine co-ligands coordinated in cis position. All the compounds were characterized using infrared, UV-visible, ( 1 H, 13 C, 31 P) NMR, ESI-MS and elemental analyses. The molecular structures of ligand H 2 L 1 and complexes 1-3 were determined using X-ray crystallography, which confirmed the coordination mode of the ligands with metals. The crystal structure of complexes 1 and 2 revealed a distorted octahedral geometry around the ruthenium ion and the structure of complex 3 indicated a tetrahedral geometry around the copper ion. With the X-ray structures, density functional theory computations were carried out to determine the electronic structure of the compounds. The interactions of complexes 1-3 with calf thymus DNA and bovine serum albumin protein were investigated using UV-visible and fluorescence spectroscopic and viscometric methods. Catecholase-and phosphatase-like activities promoted by complexes 1-3 under physiological conditions have been studied. In vitro anticancer activities have been demonstrated by MTT assay, acridine orange/ethidium bromide and diamidino-2-phenylindole staining against various cancerous cell lines.

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Section: Resultssupporting

confidence: 56%

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

Vijayan

Viswanathamurthi

Sugumar

et al. 2016

Applied Organom Chemis

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“…The 1 H NMR spectrum of H 3 L ( 6 ) in CDCl 3 shows one multiplet at 1.22 ppm and two quartets at 3.62 and 3.90 ppm, which are all assigned to the diethyl residues of the molecule due to a hindered rotation around the related C–N bonds. This is not unusual for such ligands and has been described before . The terminal alkyne proton leads to a triplet with a coupling constant of J = 2.4 Hz due to a long‐range coupling with the methylene group of the propargyl function.…”

Section: Resultssupporting

confidence: 68%

“…The development of tri‐, tetra‐, and pentadentate derivatives makes them also interesting for the complexation of rhenium and technetium, since they are suitable candidates for the stabilization of their {M V O} 3+ or {M V N} 2+ cores . Recently, we reported on some representatives of such ligands with orthogonal anchor groups in their periphery for bioconjugation and the corresponding Re and Tc complexes , . The coupling approach applied for these examples was the classical peptide coupling.…”

Section: Introductionmentioning

confidence: 99%

Propargyl‐Substituted Thiocarbamoylbenzamidines of Technetium and Rhenium: Steps towards Bioconjugation with Use of Click Chemistry

2016

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“…Ligand systems, which form stable or highly inert complexes with these cores are, among others, pentadentate N , N -dialkyl- N ′-benzoylthiourea derivatives (Chart a). , However, the tuning of the biological properties of these complexes by systematic functionalization of the organic ligand requires a huge synthetic effort . A mixed-ligand approach gives access to a much more facile and smooth tuning of the ligand properties and, thus, of the biological behavior.…”

Section: Introductionmentioning

confidence: 99%

Effect of Fluorination on the Structure and Anti-Trypanosoma cruzyActivity of Oxorhenium(V) Complexes withS,N,S-Tridentate Thiosemicarbazones and Benzoylthioureas. Synthesis and Structures of Technetium(V) Analogues

et al. 2019

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A series of 16 “3 + 2” mixed-ligand complexes of the general composition [ReO(L1)(L2)] (H2L1a–H2L1d = tridentate thiosemicarbazones having a phenyl group with 4-H, 4-F, 3,5-di-F, and 4-CF3 substituents; HL2a–HL2d = bidentate N,N-diethyl-N′-benzoylthioureas with 4-H, 4-F, 3,5-di-F, and 4-CF3 substituents at the benzoyl groups) have been synthesized and characterized by spectroscopic methods and X-ray diffraction. Irrespective of the individual fluorine substitution, the complexes are stable and possess the same general structure. Some systematic electronic effects of the fluorine-substitution patterns of the ligands have been found on the 13C NMR chemical shifts of the N–CN carbon atoms of the {L1}2– and the CO carbon atoms of the {L2}− ligands. Antiparasitic properties of the rhenium complexes have been tested against epimastigotes and trypomastigotes forms of two Trypanosoma cruzi strains and the amastigotes form of one of them. The results of this study indicate that the activity of the rhenium complexes can clearly be modulated by fluorine substitution of their ligands. Some of the fluorinated compounds show a high activity against epimastigotes and trypomastigotes forms of the parasites. Reactions between (NBu4)[TcOCl4] and two representatives of the fluorinated ligands (H2L1b, 4-F-substituted, and H2L1c, 4-CF3-substituted) form stable complexes of the composition [TcOCl(L1b)] and [TcOCl(L1c)]. Subsequent reactions of these products with HL2b (4-F-substituted) give the corresponding [TcO(L1)(L2)] mixed-ligand complexes. Also, the technetium compounds are stable as solids and in solutions and have structures corresponding to those of their rhenium analogues.

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ReVO and ReVNPh complexes with pentadentate benzamidines – Synthesis, structural characterization and DFT evaluation of isomeric complexes

Cited by 10 publications

References 31 publications

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

Propargyl‐Substituted Thiocarbamoylbenzamidines of Technetium and Rhenium: Steps towards Bioconjugation with Use of Click Chemistry

Effect of Fluorination on the Structure and Anti-Trypanosoma cruzyActivity of Oxorhenium(V) Complexes withS,N,S-Tridentate Thiosemicarbazones and Benzoylthioureas. Synthesis and Structures of Technetium(V) Analogues

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