Synthesis, characterization, and single crystal X-ray structure of the 1-furoyl-3-cyclohexylthiourea cadmium chloride complex, Cd[C4H3OC(O)NHC(S)NHC6H11]4Cl2

Duque, J.; Estévez-Hernández, O.; Reguera, E.; Ellena, Javier; Corrêa, Rodrigo S.

doi:10.1080/00958970902926795

Cited by 20 publications

(8 citation statements)

References 23 publications

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“…These are also widely used as precursors or intermediates towards the syntheisis of a variety of heterocyclic compounds (Zeng et al, 2003;D'hooghe, et al, 2005). In addition, aroylthioureas have applications in metal complexes and molecular electronics (Aly et al, 2007;Duque et al, 2009). The structure of a related compound was recently published (Yan & Xue, 2008) in which the molecule showed excellent herbicidal activity.…”

Section: -[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thioureamentioning

confidence: 98%

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

et al. 2012

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The title compound, C10H8N4O2S, was synthesized from furoyl isothiocynate and 2-aminopyrimidine in dry acetone. The two N—H groups are in an anti conformation with respect to each other and one N—H group is anti to the C=S group while the other is syn. The amide C=S and the C=O groups are syn to each other. The mean plane of the central thiourea fragment forms dihedral angles of 13.50 (14) and 5.03 (11)° with the furan and pyrimidine rings, respectively. The dihedral angle between the furan and pyrimidine rings is 18.43 (10)°. The molecular conformation is stabilized by an intramolecular N—H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, molecules are linked by pairs of N—H⋯N and weak C—H⋯S hydrogen bonds to form inversion dimers.

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Section: -[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thioureamentioning

confidence: 98%

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

et al. 2012

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“…[9,10,306] In earlier work, Otazo-Sanchez et al [9] prepared 46 thiourea derivatives and demonstrated their potential use as ionophores for ISEs. Some of these were used as potentiometric sensors for heavy metals Pb (II), Cd(II) [263,307] and Hg(II). [308] A new approach reported recently involves the generation of new organic-inorganic hybrid materials prepared by covalently anchoring 1-furoyl thiourea on mesoporous silica, which exhibited good ability to remove Hg(II) from aqueous solutions.…”

Section: Anion Receptors and Ionophoresmentioning

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

191

123

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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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“…A negative and a positive shift of about 20 to 30 cm −1 in ν(C=S) and ν(C=O) respectively, support coordination through thione sulfur . The positive shift in ν(C=O) may be attributed to the inductive effect of copper(I) that is transmitted through the −CO−NH−CS− fragment after complexation with the sulfur atom . Thione sulfur coordination is further supported by the crystal structure of [Cu (H 2 L 1 ) 2 Cl] (1) .…”

Section: Resultsmentioning

confidence: 68%

Monodentate Coordination of N, N′‐Disubstituted Thiocarbamide Ligands: Syntheses, Structural Analyses, In Vitro Cytotoxicity and DNA Damage Studies of Cu(I) Complexes

et al. 2018

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Structural analysis of three novel substituted thiocarbamide ligands N‐(naphthyl)‐N′‐(isobutoxycarbonyl) thiocarbamide (H2L1), N‐(4‐methoxyphenyl)‐N′‐(isobutoxycarbonyl) thiocarbamide (H2L2) & N‐(2‐methoxy‐4‐nitrophenyl)‐N′‐(isobutoxycarbonyl) thiocarbamide (H2L3) and their copper(I) complexes [(H2L1)2CuCl] (1), [(H2L2)2CuCl] (2) and [(H2L3)2CuCl] (3) was performed using various spectroscopic techniques (FT−IR, 1H and 13C NMR, UV‐Visible),TG analysis and single crystal X‐ray studies of (H2L1) and [(H2L1)2CuCl] (1). The copper(I) complexes possess trigonal planar geometry coordinating through two thione sulfur atoms from two ligand molecules and one chloride ion. Two intramolecular hydrogen bonding interactions present between (−N1H) and carbonyl oxygen (−N2H) and coordinated chlorine stabilize the trigonal planar structure of the complexes. Cyclic voltammogram of complexes 1–3 displayed quasireversible redox behaviour corresponding to CuI/CuII couple. Determination of in vitro cytotoxicity of ligands and their complexes using five human carcinoma cell lines 2008, C13* (cervical carcinoma), A2780, A2780/CP and IGROV‐1 (ovarian carcinoma) revealed that copper(I) complexes were more potent inhibitors than the ligands against all the cell lines. The most effective were complexes 2 and 3. The comet assay test of complexes 2 and 3 against 2008, C13* and IGROV‐1 cell lines indicated significant damage to the DNA structure.

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Synthesis, characterization, and single crystal X-ray structure of the 1-furoyl-3-cyclohexylthiourea cadmium chloride complex, Cd[C₄H₃OC(O)NHC(S)NHC₆H₁₁]₄Cl₂

Cited by 20 publications

References 23 publications

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

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

Monodentate Coordination of N, N′‐Disubstituted Thiocarbamide Ligands: Syntheses, Structural Analyses, In Vitro Cytotoxicity and DNA Damage Studies of Cu(I) Complexes

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