Synthesis, structural characterization and cytotoxicity of nickel(II) complexes containing 3,3-dialkyl/aryl-1-benzoylthiourea ligands

Selvakumaran, N.; Pratheepkumar, A.; Ng, Seik Weng; Tiekink, Edward R. T.; Karvembu, Ramasamy

doi:10.1016/j.ica.2013.04.024

Cited by 49 publications

(27 citation statements)

References 34 publications

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“…These ligands exhibit prevalent coordination systems such as neutral bidentate and monobasic bridging in some complexes [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Since the structural and conformational properties of acyl thioureas has been recognized, the use of transition metal complexes, including acylthiourea ligands, have been expanded in many different fields [9][10][11][12].…”

Section: N-(alkyl/aryl)-n'-acylthiourea and N-di(alkyl/aryl)-n´-mentioning

confidence: 99%

“…For example, acylthiourea derivatives and their Co(III) complexes have shown antibacterial [13] and antifungal [14] activities. Ni(II) complexes, containing benzoylthiourea ligands, have shown cytotoxicity against T47D cell [15] and according to the investigations water soluble platinum(II) benzoylthiourea complexes have shown considerable antimalarial activity [23,24]. Very recently, there have been many studies on noncovalent interactions acting on the crystal structure and packing of sulfur-containing compounds [25].…”

Section: N-(alkyl/aryl)-n'-acylthiourea and N-di(alkyl/aryl)-n´-mentioning

confidence: 99%

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N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

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The compound N-(dibenzylcarbamothioyl)-3-methylbutanamide as a thiourea derivative was synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound was also characterized by single crystal X-ray diffraction method. Crystal data for title compound C20H24N2OS: monoclinic, space group C2/c (no. 15), a = 19.6882(9) Å, b = 9.4045(4) Å, c = 19.5012(8) Å, β = 98.433(2)°, V = 3571.8(3) Å3, Z = 8, μ(CuKα) = 1.665 mm-1, 25057 reflections measured (9.168° ≤ 2Θ ≤ 144.196°), 3500 unique (Rint = 0.0322, Rsigma = 0.0200) which were used in all calculations. The final R1 was 0.0363 (I>2σ(I)) and wR2 was 0.0910 (all data). Intermolecular contacts obtained from X-ray single crystal diffraction study were also explored using both Hirshfeld surfaces and fingerprint plots. Hirshfeld surface analysis showed the occurrence of S···H, O···H and H···H contacts that display an important role to crystal packing stabilization of the thiourea derivative compound. In addition, the compound was evaluated for both their in-vitro antibacterial and antifungal activity.

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Section: N-(alkyl/aryl)-n'-acylthiourea and N-di(alkyl/aryl)-n´-mentioning

confidence: 99%

Section: N-(alkyl/aryl)-n'-acylthiourea and N-di(alkyl/aryl)-n´-mentioning

confidence: 99%

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

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“…52 The air stable half-sandwich Ru(II) complexes (1)(2)(3)(4)(5)(6) were prepared as orange solids in high yields (80-88%) from the reactions between [RuCl 2 (η 6 - 52 The air stable half-sandwich Ru(II) complexes (1)(2)(3)(4)(5)(6) were prepared as orange solids in high yields (80-88%) from the reactions between [RuCl 2 (η 6 - …”

Section: Synthesis Of Ru(ii)-benzene Complexesmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9] Half sandwich Ru(II) complexes having η 6 -p-cymene or η 6 -benzene unit are of recent interest due to their superior catalytic activities. [1][2][3][4][5][6][7][8][9] Half sandwich Ru(II) complexes having η 6 -p-cymene or η 6 -benzene unit are of recent interest due to their superior catalytic activities.…”

Section: Introductionmentioning

confidence: 99%

“…48 Pharmaceuticals which require chiral alcohols for their synthesis are antihypertensive, antiarrhythmic, anticholesterol and antiviral drugs, calcium and potassium channel blocking drugs and β 3 -receptor agonists. 51 In the present paper, we report the synthesis of the new Ru-benzene complexes, [RuCl 2 (η 6 -C 6 H 6 )L] (1-6), from [RuCl 2 (η 6 -C 6 H 6 )] 2 (1)(2)(3)(4)(5)(6) for ATH of ketones to their corresponding chiral alcohols is investigated and compared with similar η 6 -p-cymene complexes. 50 ATH of prochiral ketones is one of the powerful methods for the production of optically active secondary alcohols.…”

Section: Introductionmentioning

confidence: 99%

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Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Sheeba

Preethi

Nijamudheen

et al. 2015

Catal. Sci. Technol.

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The reactions of [RuCl 2 (η 6 -C 6 H 6 )] 2 with chiral aroylthiourea ligands yielded pseudo octahedral half-sandwich "piano-stool" complexes. All the Ru(II) complexes were characterized by analytical and spectral (UV-visible, FT-IR, 1 H NMR and 13 C NMR) studies. The molecular structure of the ligands (L2 and L4) and the complexes (2, 4 and 5) was confirmed by single crystal XRD. All the complexes were successfully screened as catalysts for the asymmetric transfer hydrogenation (ATH) of ketones using 2-propanol as the hydrogen source in the presence KOH. The ATH reactions proceeded with excellent yields (up to 99%) and very good enantioselectivity (up to 99% ee). The scope of the present catalytic system was extended to substituted aromatic ketones and few hetero aromatic ketones. Density functional theory (DFT) calculations predicted non-classical, concerted transition states for the ATH reactions. The catalytic activity of Ru-benzene complexes toward asymmetric reduction of ketones was significantly higher compared to analogues p-cymene complexes. Such enhanced efficiency and the product selectivity for Ru-benzene complexes compared to Ru-p-cymene complexes were rationalized by the computational study.Electronic supplementary information (ESI) available: A table of the X-ray crystallographic data, atomic coordinates in CIF format, the molecular structure of ligands L2 & L4, 1 H NMR and 13 C NMR spectra of all the ligands and complexes, GC and HPLC data are included. Cartesian coordinates, energies, and vibrational frequencies for all the reported structures, and optimized geometries and activation free energies for high energy TSs.

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Synthesis, structural and chemosensitivity studies of arene d⁶ metal complexes having N‐phenyl‐N´‐(pyridyl/pyrimidyl)thiourea derivatives

Adhikari

Hussain

Phillips

et al. 2018

Applied Organom Chemis

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The d 6 metal complexes of thiourea derivatives were synthesized to investigate its cytotoxicity. Treatment of various N-phenyl-N´pyridyl/pyrimidyl thiourea ligands with half-sandwich d 6 metal precursors yielded a series of cationic complexes. Reactions of ligand (L1-L3) with [(p-cymene)RuCl 2 ] 2 and [Cp*MCl 2 ] 2 (M = Rh/Ir) led to the formation of a series of cationic complexes bearing general formula [(arene)M(L1)к 2 (N,S) Cl] + , [(arene)M(L2)к 2 (N,S) Cl] + and [(arene) M(L3)к 2 (N,S) Cl] + [arene = p-cymene, M = Ru (1, 4, 7); Cp*, M = Rh (2, 5, 8); Cp*, Ir (3, 6, 9)]. These compounds were isolated as their chloride salts. X-ray crystallographic studies of the complexes revealed the coordination of the ligands to the metal in a bidentate chelating N,S-manner. Further the cytotoxicity studies of the thiourea derivatives and its complexes evaluated against HCT-116 (human colorectal cancer), MIA-PaCa-2 (human pancreatic cancer)and ARPE-19 (non-cancer retinal epithelium) cancer cell lines showed that the thiourea ligands displayed no activity. Upon complexation however, the metal compounds possesses cytotoxicity and whilst potency is less than cisplatin, several complexes exhibited greater selectivity for HCT-116 or MIA-PaCa-2 cells compared to ARPE-19 cells than cisplatin in vitro. Rhodium complexes of thiourea derivatives were found to be more potent as compared to ruthenium and iridium complexes.

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Synthesis, structural characterization and cytotoxicity of nickel(II) complexes containing 3,3-dialkyl/aryl-1-benzoylthiourea ligands

Cited by 49 publications

References 34 publications

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Synthesis, structural and chemosensitivity studies of arene d⁶ metal complexes having N‐phenyl‐N´‐(pyridyl/pyrimidyl)thiourea derivatives

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Synthesis, structural characterization and cytotoxicity of nickel(II) complexes containing 3,3-dialkyl/aryl-1-benzoylthiourea ligands

Cited by 49 publications

References 34 publications

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

Half-sandwich Ru(η6-C6H6) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Synthesis, structural and chemosensitivity studies of arene d6 metal complexes having N‐phenyl‐N´‐(pyridyl/pyrimidyl)thiourea derivatives

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Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Synthesis, structural and chemosensitivity studies of arene d⁶ metal complexes having N‐phenyl‐N´‐(pyridyl/pyrimidyl)thiourea derivatives