Synthesis, spectral characterization and structural studies of a novel O, N, O donor semicarbazone and its binuclear copper complex with hydrogen bond stabilized lattice

Layana, S.R.; Saritha, S.R.; Anitha, L.; Sithambaresan, M.; Sudarsanakumar, M.R.; Suma, S.

doi:10.1016/j.molstruc.2017.12.073

Cited by 20 publications

(2 citation statements)

References 38 publications

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“…Semicarbazones can function as brilliant ligands in a variety of metal ions (Kala et al, 2007) and co-ordinate to metal ions either in neutral (Siji et al, 2011) or in anionic forms (Reena et al, 2008). Structural studies of many semicarbazones and N 4 -phenylsemicarbazones have been reported and some of them adopt an E configuration with respect to the azomethine double bond along with both inter-and intramolecular hydrogen-bonding interactions (Reena et al, 2010;Layana et al, 2014Layana et al, , 2018. Semicarbazones form complexes with a variety of structural ISSN 2056-9890 features such as monomer, dimer and one-dimensional polymers (Kunnath et al, 2016).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 2-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-N-phenylhydrazinecarboxamide

et al. 2019

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The title compound crystallizes with two independent molecules in the asymmetric unit. The semicarbazone moieties of which are essentially planar with the terminal phenyl rings twisted away from them. In the crystal, N—H⋯O hydrogen-bonding interactions link the two molecules into a centrosymmetric dimer, with adjacent dimers linked by weak C—H⋯O interactions to form a cage-like structure. These cage structures are interconnected by weak C—H⋯π interactions, forming supramolecular chains along the c-axis direction.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 2-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-N-phenylhydrazinecarboxamide

et al. 2019

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“…Semicarbazones have been extensively investigated owing to their potential applications in biological and pharmacological fields 5 – 7 . These are important classes of compounds which can coordinate with many metal ions because of the presence of donor atoms such as nitrogen and oxygen in their core structure 8 – 10 . In biological systems, C-demethylation occur in histones and DNA, catalysed by enzymes/chemical agents 11 , 12 .…”

Section: Introductionmentioning

confidence: 99%

C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications

Sennappan

Skariyachan

Managutti

et al. 2020

Sci Rep

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A Novel (E)-2-(1-(3-aminophenyl)ethylidene)hydrazinecarboxamide 1 was synthesized by traditional method and converted to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide 2 by single step in DMSO at room temperature. Synthesized compound 1 was analysed by spectroscopy (NMR and LC–MS) techniques and molecule 2 was characterized using single crystal X-ray diffraction and spectroscopy (NMR and GC–MS) techniques. These analytical technique results revealed that, C-demethylation and 1, 2 amino shift in phenyl ring of compound 1 gives molecule 2. DNA binding studies of compounds 1 and 2 was carried out by electronic absorption spectroscopy. This result revealed that, compounds 1 and 2 showed hyperchromism with bathochromic shift. Anticancer activity of compounds 1 and 2 is carried out by molecular docking with five receptors.Computer aided virtual screening demonstrated that the synthesized molecules possess ideal drug likeliness, pharmacokinetics features, toxicity profile for structure based drug discovery. The molecular docking studies revealed that the synthesized molecules are significant binding with the five selected cancer receptors with minimum binding energy (kcal/mol), number of hydrogen bonds, weak interaction, docking score and cluster RMS. The docking studies also suggested that the molecules showed interactions with DNA and the theoretical values of the binding are comparable with that of the experimental values. Hirshfeld surface analysis was used to analyze and quantify the intermolecular interactions in the crystal structure of compound 2.

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Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

Shi

Nie

et al. 2020

Applied Organom Chemis

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A Cu(II)–coumarin complex, [CuL2(NO3)2] (2), where L = 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin (1), was synthesized with Cu(NO3)2⋅3H2O and characterized using elemental, infrared and single‐crystal X‐ray diffraction analyses. The crystal structure of 1 shows that all the pyrone, benzene and pyridine rings are completely coplanar. The crystal structure of 2 is stabilized by intermolecular C–H···O and C–H···N hydrogen bonds and C···C short contacts, which lead to the formation of a two‐dimensional network structure. Density functional theory results give support to the experimentally determined monomeric structure. The in vitro cytotoxic activities of 1 and 2 were investigated against HeLa (cervical carcinoma), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein) cells by MTT assay. The IC50 values show that both 1 and 2 have lower toxicity than doxorubicin and cisplatin in every case. Ligand 1 exhibits higher anti‐HeLa activity than doxorubicin. Complex 2 displays higher anti‐HeLa activity than coumarin but lower than that of cisplatin. Various spectroscopic approaches indicate that 1 and 2 could effectively bind with DNA through intercalation mode.

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Synthesis, spectral characterization and structural studies of a novel O, N, O donor semicarbazone and its binuclear copper complex with hydrogen bond stabilized lattice

Cited by 20 publications

References 38 publications

Crystal structure of 2-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-N-phenylhydrazinecarboxamide

Crystal structure of 2-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-N-phenylhydrazinecarboxamide

C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications

Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

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