N,N-Disubstituted-N′-acylthioureas as modular ligands for deposition of transition metal sulfides

Ali, Zahra; Richey, Nathaniel E.; Bock, Duane C.; Abboud, Khalil A.; Akhtar, Javeed; Sher, Muhammad; McElwee‐White, Lisa

doi:10.1039/c7dt04860b

Cited by 16 publications

(4 citation statements)

References 38 publications

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“…The average bond lengths of the thiocarbonyl (S(1) – C(2) = 1.714–1.727 Å) and carbonyl (O(1)–C(1) = 1.256–1.261 Å) groups in the complexes are longer than the respective bond lengths of the free ligands. The C–N (C(1)–N(1) = 1.306–1.317 Å; C(2)–N(1) = 1.336–1.353 Å) distances are shorter than both the free ligands. ,,, These fragment (SCNCO) bond length values are between double and single bonds, showing evidence of the existence of π-electron delocalization in a six-membered chelate ring formed with the bidentate coordination of acylthiourea. , These results are consistent with those described in the literature, where bidentate (S, O) or monobasic coordinations are the most common type of coordination for this class of ligands to a metal center. − …”

Section: Resultssupporting

confidence: 89%

“…61,41,62,63 These fragment (SCNCO) bond length values are between double and single bonds, showing evidence of the existence of π-electron delocalization in a six-membered chelate ring formed with the bidentate coordination of acylthiourea. 64,65 These results are consistent with those described in the literature, where bidentate (S, O) or monobasic coordinations are the most common type of coordination for this class of ligands to a metal center. 66−68 Free acylthioureas exhibit a band in their FTIR spectra ranging from 3190 to 3120 cm −1 , assigned as N−H stretching vibrations (Table S2).…”

Section: ■ Experimental Sectionsupporting

confidence: 92%

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Experimental and Theoretical DFT Study of Cu(I)/N,N-Disubstituted-N′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells

et al. 2021

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Six complexes with the general formula [Cu(acylthioureato)(PPh3)2] were synthesized and characterized using spectroscopic techniques (IR, UV/visible, and 1D and 2D NMR), mass spectrometry, elemental analysis, and X-ray diffraction. Interpretation of the in vitro cytotoxicity data of Cu(I) complexes took into account their stability in cell culture medium. DFT calculations showed that NMR properties, such as the shielding of carbon atoms, are affected by relativistic effects, supported by the ZORA Hamiltonian in the theoretical calculations. Additionally, the calculation of the energies of the frontier molecular orbitals predicted that the structural changes of the acylthiourea ligands did not cause marked changes in the reactivity descriptors. All complexes were cytotoxic to the evaluated tumor cell lines [MDA-MB-231 (triple-negative breast cancer, TNBC), MCF-7 (breast cancer), and A549 (lung cancer)]. In the MDA-MB-231 cell line, complex 1 significantly altered the cytoskeleton of the cells, reducing the density and promoting the condensation of F-actin filaments. In addition, the compound caused an increase in the percentage of cells in the fragmented DNA region (sub-G0) and induced cell death via the apoptotic pathway starting at the IC50 concentration. Taken together, the results show that complex 1 has cytotoxic and apoptotic effects on TNBC cells, which is a cell line originating from an aggressive, difficult-to-treat breast cancer.

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Section: Resultssupporting

confidence: 89%

Section: ■ Experimental Sectionsupporting

confidence: 92%

Experimental and Theoretical DFT Study of Cu(I)/N,N-Disubstituted-N′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells

et al. 2021

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“…The last four decades witnessed a wide exploration in the coordination chemistry of aroylthioureas, which mainly focuses on the metal complexes of the basic benzoyl(N,N-dialkylthioureas) HL I , [1][2][3][4][5][6][7][8][9] and the bipodal iso-phthaloylbis(N,N-dialkylthioureas) H2L II (figure 1). [10][11][12][13][14][15] In most of structurally determined complexes, aroylthiourea moieties deprotonate and form bidentate (S,O)-chelators (figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Figure 1: Mono-and bi-podal aroylthioureas and their metal complexes [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Recently, novel bipodal aroylbis(thioureas) incorporating modified aromatic spacers such as pyridine (H2L 1 ) and catechol (H2L 2 ) have been developed. They offer completely different coordination abilities.…”

Section: Introductionmentioning

confidence: 99%

Ammonium‐Iron(III) metallacryptate inclusion complexes based on Aroylbis(N,N‐diethylthioureas): Synthesis and structure

Huy,

Abram,

Thang

2022

Vietnam Journal of Chemistry

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One‐pot reactions of pyridine‐ or catechol‐scaffolding aroylbis(N,N‐diethylthioureas), H2L1 or H2L2, with methanolic solutions of FeCl3 and NH4Cl bring about novel cationic ammonium‐inclusion complexes {NH4 ⊂ [Fe2(L)3]}+ (L = L1 or L2), which could be separated as PF6– salts. The inclusion compounds have been characterized by elemental analyses and spectroscopic methods such as HRMS, IR and SCXRD. Ammonium ions are captured in the intramolecular voids of {2}‐metallacryptands {[Fe2(L)3]} (L = L1 or L2) resulting from the octahedral coordination of Fe3+ ions with aroylthiourea moieties of the ligands. Hydrogen bonds are established between the NH4+ ions and the donor atoms of the cages.

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Synthesis and Characterization of Copper(I) Halide Complexes Prepared with Bipodal Diacylthioureas

et al. 2020

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Bipodal diacylthioureas [MesC(O)NHC(S)NH]2R (R = C6H4‐1,2 (L1, 1), C6H4‐1,4 (L2, 2)) were synthesized, and their complexation reactions with equimolar Cu(I) halides CuX (X = Cl, Br, ) were investigated. The obtained ligands L1–2 and the resultant Cu(I) complexes (3–8) were characterized by FT‐IR, 1H NMR, 13C NMR spectroscopy, elemental analysis and single‐crystal X‐ray diffraction. The complexation of L1 with CuX gave three different 1D polymers: the infinite single chain (L1CuCl)n (3), edge‐shared double‐ring chain {[(µ‐L1)CuBr]2}n (4), and vertex‐shared double‐ring chain {[L1Cu(µ‐I)]2}n (5). Similarly, but more pronounced, the treatment of L2 with CuX resulted in the formation of 1D edge‐shared double‐ring chain {[(µ‐L2)CuCl]2}n (6), 0D discrete dinuclear metallamacrocyclic ring (L2CuBr)2 (7), and 3D network polymer [L2Cu(µ‐I)]n (8), respectively. The structural diversity may be related to the suitable spacer, flexible C=S directionality and binding roles of halide anions and sulfur donors. Among Cu(I) complexes (3–8) as prepared, both chloride (in 3 and 6) and bromide anions (in 4 and 7) acted as terminal ligands, while the iodide anions (in 5 and 8) served as bridging ligand. In contrast, only in edge‐shared double‐ring chains (4 and 6) it was found that the sulfur donors (one of two in each Ln) played as the bridging ligand.

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N,N-Disubstituted-N′-acylthioureas as modular ligands for deposition of transition metal sulfides

Cited by 16 publications

References 38 publications

Experimental and Theoretical DFT Study of Cu(I)/N,N-Disubstituted-N′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells

Experimental and Theoretical DFT Study of Cu(I)/N,N-Disubstituted-N′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells

Ammonium‐Iron(III) metallacryptate inclusion complexes based on Aroylbis(N,N‐diethylthioureas): Synthesis and structure

Synthesis and Characterization of Copper(I) Halide Complexes Prepared with Bipodal Diacylthioureas

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