Crystal structures, spectroscopic properties of new cobalt(II), nickel(II), zinc(II) and palladium(II) complexes derived from 2-acetyl-5-chloro thiophene thiosemicarbazone: Anticancer evaluation

Şen, Betül; Kalhan, Hatice Kübra; Demir, Volkan; Güler, Egemen Erdem; Kayalı, Hülya Ayar; Subaşı, Elif

doi:10.1016/j.msec.2018.12.080

Cited by 28 publications

(11 citation statements)

References 67 publications

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“…For compounds 2, 5, and 8, the aromatic proton signals of the phenyl fragment bound to the pyridine ring were affected by the presence of the fluoro, methoxy, and chloro substituents in the C-4′, C-3′,4′, and C-3′,5′positions, respectively. ese signals are deshielded for the protons in e signals observed at δ = 178.98 − 171.65 correspond to the thioamide carbons (C=S) [33,38,39]. e resonance lines of the pyridine carbons appeared at δ = 161.87 − 94.95, and these chemical shifts are in agreement with those found for 2-benzoylpyridine-N(4)-orthofluorphenyl thiosemicarbazone (δ = 124.96−151.18) [7].…”

Section: Nmr Spectrasupporting

confidence: 79%

Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives

Hernández

Carrasco

Vaisberg

et al. 2020

Journal of Chemistry

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Eight new thiosemicarbazone derivatives, 6-(1-trifluoroethoxy)pyridine-3-carbaldehyde thiosemicarbazone (1), 6-(4′-fluorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (2), 5-chloro-pyridine-3-carbaldehyde thiosemicarbazone (3), 2-chloro-5-bromo-pyridine-3-carbaldehyde thiosemicarbazone (4), 6-(3′,4′-dimethoxyphenyl)pyridine-3-carbaldehyde thiosemicarbazone (5), 2-chloro-5-fluor-pyridine-3-carbaldehyde thiosemicarbazone, (6), 5-iodo-pyridine-3-carbaldehyde thiosemicarbazone (7), and 6-(3′,5′-dichlorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (8) were synthesized, from the reaction of the corresponding pyridine-3-carbaldehyde with thiosemicarbazide. The synthesized compounds were characterized by ESI-Mass, UV-Vis, IR, and NMR (1H, 13C, 19F) spectroscopic techniques. Molar mass values and spectroscopic data are consistent with the proposed structural formulas. The molecular structure of 7 has been also confirmed by single crystal X-ray diffraction. In the solid state 7 exists in the E conformation about the N2-N3 bond; 7 also presents the E conformation in solution, as evidenced by 1H NMR spectroscopy. The in vitro antitumor activity of the synthesized compounds was studied on six human tumor cell lines: H460 (lung large cell carcinoma), HuTu80 (duodenum adenocarcinoma), DU145 (prostate carcinoma), MCF-7 (breast adenocarcinoma), M-14 (amelanotic melanoma), and HT-29 (colon adenocarcinoma). Furthermore, toxicity studies in 3T3 normal cells were carried out for the prepared compounds. The results were expressed as IC50 and the selectivity index (SI) was calculated. Biological studies revealed that 1 (IC50 = 3.36 to 21.35 μM) displayed the highest antiproliferative activity, as compared to the other tested thiosemicarbazones (IC50 = 40.00 to >582.26 μM) against different types of human tumor cell lines. 1 was found to be about twice as cytotoxic (SI = 1.82) than 5-fluorouracile (5-FU) against the M14 cell line, indicating its efficiency in inhibiting the cell growth even at low concentrations. A slightly less efficient activity was shown by 1 towards the HuTu80 and MCF7 tumor cell lines, as compared to that of 5-FU. Therefore, 1 can be considered as a promising candidate to be used as a pharmacological agent, since it presents significant activity and was found to be more innocuous than the 5-FU anticancer drug against the 3T3 mouse embryo fibroblast cells.

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Section: Nmr Spectrasupporting

confidence: 79%

Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives

Hernández

Carrasco

Vaisberg

et al. 2020

Journal of Chemistry

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“…Also, the 1 H-NMR spectrum of the Cd(II) complex displays aromatic protons in the region of d 6.77-9.15 ppm as complex multiplets. 70,71 On adding D 2 O, the signals attributable to the protons of two NH groups were removed entirely while the other signals remained at the same locations. This statement was conrmed the infrared assignment.…”

Section: Spectroscopic and Magnetic Studiesmentioning

confidence: 99%

Co(ii), Ni(ii), Cu(ii) and Cd(ii)-thiocarbonohydrazone complexes: spectroscopic, DFT, thermal, and electrical conductivity studies

et al. 2021

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“…Rafi et al reported the synthesis of pyridazine‐based binuclear zinc (II) complexes with HOMO‐LUMO gap of 1.35 eV evaluated by the DFT calculations . [ 65 ] In 2015, Zinc halide complexes based on bis (pyrazol‐1‐yl) methane ligand were also synthesized and their HOMO‐LUMO gap value of 3.30 eV was calculated by the DFTmethod. [ 66 ] Therefore, the synthesized zinc (II) based complexes in this study have more stability than the reported ones.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structural characterization, and density functional theory calculations of the two new Zn (II) complexes as antibacterial and anticancer agents with a neutral flexible tetradentate pyrazole‐based ligand

Beheshti

Bahrani‐Pour

Kolahi

et al. 2021

Applied Organom Chemis

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Two new mono‐ and dinuclear zinc (II) complexes with a formula of [Zn (LN)OMeCl] (1) and [Zn2(LN)(N3)2Cl2] (2) [where LN = 1,1,3,3‐tetrakis(3,5‐dimethyl‐1‐pyrazolyl)propane)] have been synthesized in methanol as a solvent and fully characterized by the single crystal X‐ray diffraction, elemental analysis, FT‐IR, UV–Vis, density functional theory (DFT) calculations, antibacterial, and anticancer properties. In both of them, zinc ion is tetrahedrally coordinated to two nitrogen atoms from one of the chelating bidentate bis(3,5‐dimethylpyrazolyl)methane units of the LN ligand and one terminal chlorine. The forth coordination site was occupied by methoxy group in 1 and azide co‐ligand in complex 2. In contrast to 1, in the structure of 2 two metal centers are bridged by the tetradentate chelating LN ligand to form a dinuclear complex. Interestingly, the environment around the central atom in these complexes are mimicked with the core structure of the zinc metalloproteinases, Thermolysin {[NNO]ZnX} and Carbonic anhydrase {[NNN]ZnX} for complexes 1 and 2, respectively. Data analysis of the antibacterial activities demonstrated that the gram positive species showed more sensitivity toward the target title agents. Although, both complexes exhibit antibacterial activities and kill bacteria at low concentration, but complex 1 has higher DNA cleavage activity than 2. Additionally, the cytotoxicity of the free ligand and its complexes was evaluated against the human carcinoma cell line (Caco‐2) by the MTT method and the IC50 values were calculated for all of them. Due to the presence of pyrazole rings in the structure of the ligand and its complexes, these materials have a substantial potential to inhibit cancer cell metastasis. The energetic stabilization due to donor‐acceptor interactions in terms of the natural bond orbital (NBO) analyses and nonlinear optical properties were also examined by using the DFT calculations.

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Crystal structures, spectroscopic properties of new cobalt(II), nickel(II), zinc(II) and palladium(II) complexes derived from 2-acetyl-5-chloro thiophene thiosemicarbazone: Anticancer evaluation

Cited by 28 publications

References 67 publications

Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives

Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives

Co(ii), Ni(ii), Cu(ii) and Cd(ii)-thiocarbonohydrazone complexes: spectroscopic, DFT, thermal, and electrical conductivity studies

Synthesis, structural characterization, and density functional theory calculations of the two new Zn (II) complexes as antibacterial and anticancer agents with a neutral flexible tetradentate pyrazole‐based ligand

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