Crystal structure and properties of (Z)-N′-((E)-2-(hydroxyimino)-1-phenylethylidene) isonicotinohydrazide

Zülfıkaroğlu, Ayşın; Yüksektepe, Çiğdem; Batı, Hümeyra; Çalışkan, Nezihe; Büyükgüngör, Orhan

doi:10.1007/s10947-009-0171-3

Cited by 22 publications

(8 citation statements)

References 6 publications

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“…Also, the optimized structure of ligand has intramolecular hydrogen bond between the carbonyl oxygen and hydrogen on N 2 atom which has bond length in the range of the x-ray reported values for isonicotinic derivatives [37]. The metal complexes data indicated that there are distortion in bond lengths around the metal ion where in Cu(II), e.g., the difference in bond lengths ~0.2-0.3 Å leading to distortion in the square planar structure around Cu(II) ion [7,37].…”

Section: Molecular Modeling Of Heitsc and Its Metal Complexesmentioning

confidence: 95%

“…The data of Ni(II) complex indicated that it has more angle distortion where the lest deviated angle is O Solv -M-O with 0.26° and the most one is Cl-M-O solv (16.99°).Finally, table 9 displays selected bond length of optimized structure for ligand and its Cu(II) and Ni(II) complexes. The bond length data of HEITsc showed good agreement between DFT and the x-ray values of analogue molecules (difference up to 0.02 Å)[37][38][39]. The difference may be due to that the theoretical calculations done for isolated molecules in gaseous state, where the intermolecular columbic interactions are absent while the experimental belong to the molecules in solid state…”

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confidence: 99%

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Synthesis, spectral and structural studies on some new isonicotinic thiosemicarbazide complexes and its biological activity

Orif

Abdel‐Rhman

2015

Polyhedron

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Section: Molecular Modeling Of Heitsc and Its Metal Complexesmentioning

confidence: 95%

mentioning

confidence: 99%

Synthesis, spectral and structural studies on some new isonicotinic thiosemicarbazide complexes and its biological activity

Orif

Abdel‐Rhman

2015

Polyhedron

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“…Therefore, there is extensive research for new molecules that may be used as an optimal treatment for cancer . Oximes and hydrazones are categories of Schiff base compounds, and are an interesting class of coordinating ligands possessing robust applications in analytical, biological and chemical fields . One of the striking features of this class of ligands and its complexes is their resemblance with bio‐molecules like proteins and nucleic acids.…”

Section: Introductionmentioning

confidence: 99%

“…One of the striking features of this class of ligands and its complexes is their resemblance with bio‐molecules like proteins and nucleic acids. Hydrazones have a wide variety of applications, such as hole transporting agents in organic photoconductor layers, in the pharmaceutical industry as drugs for the treatment of cancer, schizophrenia, leprosy, etc . They also have various biological activities, such as anti‐microbial, analgesic, anti‐inflammatory, anti‐convulsant, anti‐urease and anti‐tumor activities …”

Section: Introductionmentioning

confidence: 99%

“…[4] Oximes and hydrazones are categories of Schiff base compounds, and are an interesting class of coordinating ligands possessing robust applications in analytical, biological and chemical fields. [5] One of the striking features of this class of ligands and its complexes is their resemblance with bio-molecules like proteins and nucleic acids. Hydrazones have a wide variety of applications, such as hole transporting agents [5] in organic photoconductor layers, in the pharmaceutical industry as drugs for the treatment of cancer, schizophrenia, leprosy, etc.…”

Section: Introductionmentioning

confidence: 99%

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In vitro cytotoxic and apoptotic effect of vic‐dioxime ligand and its metal complexes

Çelik

Sarikavakli

Aslantürk

2019

Applied Organom Chemis

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In this study, vic‐dioxime ligand, (1E,2E)‐2‐(hydroxyimino)‐N′‐[(1E)‐2‐oxo‐2‐phenylethylidene]ethanehydroximohydrazide (LH2), and its Cu (II) and Ni (II) transition metal complexes were synthesized and characterized using analytical and spectroscopic techniques. Furthermore, in vitro cytotoxic and apoptotic effects of this vic‐dioxime ligand and its Cu (II) and Ni (II) complexes on Caco‐2 heterogeneous human epithelial colorectal adenocarcinoma cells were evaluated. The effect of the vic‐dioxime ligand and its Ni (II) and Cu (II) complexes in combination with Campto on the cells was also investigated. The cytotoxicity test was carried using the MTT assay, and the apoptotic effect was tested by DNA diffusion assay. Campto was used as a standard anti‐cancer drug, Caco‐2 cancer cells treated with dimethylsulfoxide acted as solvent control, and human peripheral lymphocytes were used as control. The ligand and its complexes exhibit concentration‐dependent cytotoxic and apoptotic behavior. The ligand induces the weakest cytotoxic and apoptotic effects on both Caco‐2 cancer cells and lymphocytes. The Ni (II) complex of ligand induces high cytotoxic and apoptotic effects on both Caco‐2 cancer cells and lymphocytes. The Cu (II) complex of ligand has high cytotoxic and apoptotic effects on Caco‐2, but weak cytotoxic and apoptotic effects on lymphocytes. The cytotoxic and apoptotic effects of the ligand and its Ni (II) and Cu (II) complexes were found to be concentration dependent, i.e. the higher the concentration is the more cytotoxic it will be. The present findings suggest that Cu (II) complex has the potential to act as a promising anti‐cancer compound against Caco‐2 colon cancer cells.

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Synthesis, Spectral, Modeling, Docking and Cytotoxicity Studies on 2‐(2‐aminobenzoyl)‐N‐ethylhydrazine‐1‐carbothioamide and its divalent metal complexes

Hosny

Hussien

Motawa

et al. 2020

Applied Organom Chemis

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Co (II), Ni (II) and Zn (II) complexes have been synthesized. The structures of the isolated compounds were suggested based on elemental analyses, spectral analyses (FTIR, 1 H and 13 CNMR, MS, ESR and UV-Visible) and magnetic moments measurements. The free ligand exists in the keto-thione form, while in the metal complexes; it exists in the enol form and coordinates as mononegative bidentate via deprotonated enolic oxygen and N 2 H nitrogen. Both Co (II) and Ni (II) complexes have an octahedral, while Cu (II) complex has a square planar geometry. The compounds have direct electronic transitions with optical band gap (E g) values in the range 3.14-3.40 eV. The ligand and its complexes were optimized using DFT/B3LYP methodology. The ligand optimization results supported the involvement of the carbonyl oxygen, thione sulfur and N 2 H hydrogen atoms in hydrogen bonding formation. Furthermore, the obtained structures of the ligand and its complexes were subjected to molecular docking study to predict interactions cause their cytotoxicity. Finally, the in vitro cytotoxicity activities of the ligand and its complexes were investigated against Hela and WISH cell lines where the Zn (II) complex exhibited higher activity than the other compounds against the two cell lines in accordance with molecular docking suggestion.

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Crystal structure and properties of (Z)-N′-((E)-2-(hydroxyimino)-1-phenylethylidene) isonicotinohydrazide

Cited by 22 publications

References 6 publications

Synthesis, spectral and structural studies on some new isonicotinic thiosemicarbazide complexes and its biological activity

Synthesis, spectral and structural studies on some new isonicotinic thiosemicarbazide complexes and its biological activity

In vitro cytotoxic and apoptotic effect of vic‐dioxime ligand and its metal complexes

Synthesis, Spectral, Modeling, Docking and Cytotoxicity Studies on 2‐(2‐aminobenzoyl)‐N‐ethylhydrazine‐1‐carbothioamide and its divalent metal complexes

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