A quantum mechanical study of the stability and structural properties of substituted acylthiourea compounds

Woldu, Mengistu Ghebreysus; Dillen, Jan

doi:10.1007/s00214-008-0451-6

Cited by 21 publications

(16 citation statements)

References 46 publications

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“…[151,178,217] Following Woldu and Dillen, [218] the four main forms can be denoted as S, U, M and Z, where the letter reflects the position of the C=O and C=S double bonds relative to the vertically drawn N−H bond (Scheme 11). In a recent article, Becker and coworkers [216] analyzed 739 structures containing the −C(C=O)N(C=S)N− moiety found in the Cambridge Crystallographic Database.…”

Section: Conformational and Structural Propertiesmentioning

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

198

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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Section: Conformational and Structural Propertiesmentioning

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

198

123

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“…The conformation between the thiocarbonyl and the carbonyl groups of metal-free ligands is twisted [50,51,52]. After coordination, the conformation of the N'N'-dibenzyl group changed significantly.…”

Section: Crystal Structure and Molecular Assembly Analysis Of Complexmentioning

confidence: 99%

Ru(II)-based complexes with N-(acyl)-N′,N′-(disubstituted)thiourea ligands: Synthesis, characterization, BSA- and DNA-binding studies of new cytotoxic agents against lung and prostate tumour cells

Corrêa

Oliveira

Delolo

et al. 2015

Journal of Inorganic Biochemistry

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Four ruthenium(II)-based complexes with N-(acyl)-N',N'-(disubstituted)thiourea derivatives (Th) were obtained. The compounds, with the general formula trans-[Ru(PPh3)2(Th)(bipy)]PF6, interact with bovine serum albumin (BSA) and DNA. BSA-binding constants, which were in the range of 3.3-6.5×10(4) M(-1), and the thermodynamic parameters (ΔG, ΔH and ΔS), suggest spontaneous interactions with this protein by electrostatic forces due to the positive charge of the complexes. Also, binding constant by spectrophotometric DNA titration (Kb = 0.8-1.8×10(4) M(-1)) and viscosity studies indicate weak interactions between the complexes and DNA. Cytotoxicity assays against DU-145 (prostate cancer) and A549 (lung cancer) tumour cells revealed that the complexes are more active in tumour cells than in normal (L929) cells, and that they present high cytotoxicity (low IC50 values) compared with the reference metallodrug, cisplatin.

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“…The infrared and Raman spectra were also interpreted in terms of a C S point group model [7]. More recent quantum chemical calculations on small model compounds [8] reveal that the central -C(O)NHC(S)NH 2 group can display several conformations, depending on the dihedral values around the acyl-N bond and the adjacent N-C bond [9].…”

Section: Introductionmentioning

confidence: 99%

Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: An experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea

Saeed

Khurshid

Bolte

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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A quantum mechanical study of the stability and structural properties of substituted acylthiourea compounds

Cited by 21 publications

References 46 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

Ru(II)-based complexes with N-(acyl)-N′,N′-(disubstituted)thiourea ligands: Synthesis, characterization, BSA- and DNA-binding studies of new cytotoxic agents against lung and prostate tumour cells

Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: An experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea

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