Supramolecular architectures and crystal structures of gold(III) compounds with semicarbazones

Gatto, Claudia C.; Lima, Iariane J.; Chagas, Marcio A. S.

doi:10.1080/10610278.2016.1227440

Cited by 6 publications

(2 citation statements)

References 38 publications

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“…Phenyl group in a molecule is delocalized bonding structure, confirms C–C bond lengths of ring in the ranging from 1.371(5) to 1.401(4) Å 31 . The bond length of C1-O1 is 1.250(3) Å; it is a characteristic of amide carbonyl group of semicarbazone 32 . The bond lengths of C4-N4 1.355(3) Å, N4-H4B 0.860(0) Å and N4-H4 0.860(1) Å, these bonds reveals that amino group attached to phenyl ring 33 .…”

Section: Resultsmentioning

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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Section: Resultsmentioning

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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“…are observed with a distance of 3.290 Å. Additionally, cation-anion interactions and hydrogen bonds are observed (Figure 4a) and contribute to the formation of supramolecular architectures [38]. In (2), the intermolecular hydrogens bonds were formed between the atoms N(4)-H(4 4b).…”

Section: Structural Analysismentioning

confidence: 97%

Crystal Design, Antitumor Activity and Molecular Docking of Novel Palladium(II) and Gold(III) Complexes with a Thiosemicarbazone Ligand

Gatto

Almeida

Nascimento

et al. 2023

IJMS

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The current research describes the synthesis and characterization of 2-acetylpyridine N(4)-cyclohexyl-thiosemicarbazone ligand (HL) and their two metal complexes, [Au(L)Cl][AuCl2] (1) and [Pd(L)Cl]·DMF (2). The molecular structures of the compounds were determined by physicochemical and spectroscopic methods. Single crystal X-ray diffraction was employed in the structural elucidation of the new complexes. The complexes showed a square planar geometry to the metal center Au(III) and Pd(II), coordinated with a thiosemicarbazone molecule by the NNS-donor system and a chloride ion. Complex (1) also shows the [AuCl2]− counter-ion in the asymmetric unit, and complex (2) has one DMF solvent molecule. These molecules play a key role in the formation of supramolecular structures due to different interactions. Noncovalent interactions were investigated through the 3D Hirshfeld surface by the dnorm function and the 2D fingerprint plots. The biological activity of the compounds was evaluated in vitro against the human glioma U251 cells. The cytotoxicity results revealed great antitumor activity in complex (1) compared with complex (2) and the free ligand. Molecular docking simulations were used to predict interactions and properties with selected proteins and DNA of the synthesized compounds.

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Two Cu(I) complexes based on semicarbazone ligand: synthesis, crystal structure, Hirshfeld surface and anticancer activity evaluation against human cell lines

et al. 2019

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Supramolecular architectures and crystal structures of gold(III) compounds with semicarbazones

Cited by 6 publications

References 38 publications

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

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

Crystal Design, Antitumor Activity and Molecular Docking of Novel Palladium(II) and Gold(III) Complexes with a Thiosemicarbazone Ligand

Two Cu(I) complexes based on semicarbazone ligand: synthesis, crystal structure, Hirshfeld surface and anticancer activity evaluation against human cell lines

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