Facile synthesis, characterization, nucleic acid interaction and photoluminescent properties of (E)-furan-2-yl(2-(2-hydroxybenzylidene)hydrazinyl) methaniminium and its Mn(II), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes

Sennappan, M.; Krishna, P. Murali; Krishna, R. Hari

doi:10.1016/j.molstruc.2018.10.037

Cited by 11 publications

(5 citation statements)

References 37 publications

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“…The C2-N3 bond length is 1.281(3) Å indicates that it is a characteristic of azomethine group 30 . 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 .…”

Section: Resultsmentioning

confidence: 88%

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: 88%

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

Self Cite

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“…The second band occurs at 340, which may be ascribed to n-π* transitions. The last band occurring at 398 nm, may be related to charge transfer within the entire molecule [53,54].…”

Section: Characterization Of the Ligand; Dhnaphmentioning

confidence: 99%

“…It catalyzes many reactions [45]. The Co, Ni and Cu-complexes have an interest role in bioinorganic chemistry such as antibacterial, antifungal, anticancer, DNA cleavage, antioxidant and DNA binding activities [46][47][48][49][50][51][52][53][54][55].…”

Section: Introductionmentioning

confidence: 99%

Binuclear Co(II), Ni(II) and Cu(II) Complexes of a new Bis(tridentate) Hydrazone Ligand: Synthesis, Thermal, Spectroscopic, Biological, Molecular Docking and Theoretical Studies

Samy

2021

Preprint

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A new hydrazone ligand; 4,6-bis(2-hydroxynaphthalen-1-yl)methyl-ene)hydrazono)ethyl)benzene-1,3-diol (H4L; DHNAPH) was synthesized by the reaction of 4,6-bis(1-hydrazonoethyl)benzene-1,3-diol (NH2DAR) with 2-hydroxy 1-naphthaldehyde. Co(II), Ni(II) and Cu(II)- complexes ([M2L(H2O)6].nH2O.mEtOH; M = Co, Ni or Cu, n = 0.5 or 1 and m = 0.5 or 0) of DHNAPH have been successfully synthesized. Characterization of DHNAPH and its complexes was performed by analytical, spectral (IR, mass, UV-Vis, 1H NMR and ESR), magnetic susceptibility, molar conductivity and thermal gravimetric analysis (TGA) techniques. The scanning electron microscopy (SEM) was used for detection of the morphology of DHNAPH and its Co- and Ni-complexes, which refers that the DHNAPH complexes are in the nano scale. The analytical data, magnetic moments and spectral studies recognized octahedral geometries for DHNAPH complexes. DHNAPH acts as a bis(dibasic triadentate) via (C=Nazomethine and 2 OH) with metal in complexes. The optimized structure of DHNAPH and its complexes has been done theoretically by Hyperchem program and structural parameters were linked with the IR experimental data. The activity of DHNAPH and its complexes against Hepatocellular carcinoma, fungi and bacteria has been tested. The new complexes are more active than DHNAPH and the highest antitumor activity was given by copper(II) complex. The DNA-binding of DHNAPH and Cu- DHNAPH has been investigated. Molecular docking studies showed that all the tested compounds show good binding score revealing good fitting in between the DNA strands. There is agreement between docking data and DNA binding results.

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“…Hydrazones of this type have also been used in the study of interactions of DNA with small organic or metal-organic molecules to help the development of new drugs. Indeed, the elucidation of the mechanisms involved in the interaction of DNA with these small molecules makes it possible to develop models (Sathyadevi et al, 2012;Sennappan et al, 2019). In this paper, we report the synthesis and the characterization of the title compound, obtained from the condensation reaction between furoic acid hydrazide and 4-aminobenzaldehyde.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure ofN′-[4-(dimethylamino)benzylidene]furan-2-carbohydrazide monohydrate

et al. 2020

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The condensation of 2-furoic hydrazide and 4-dimethyl aminobenzaldehyde in ethanol yielded a yellow solid formulated as the title compound, C14H15N3O2·H2O. The crystal packing is stabilized by intermolecular O(water)—H...O,N(carbohydrazide) and N—H...O(water) hydrogen bonds, which form a two-dimensional network along the bc plane. Additional C—H...O interactions link the molecules into a three-dimensional network. The dihedral angle between the mean planes of the benzene and the furan ring is 34.47 (6)°. The carbohydrazide moiety, i.e., the C=N—N—C=O fragment and the benzene ring are almost coplanar, with an angle of 6.75 (9)° between their mean planes.

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Facile synthesis, characterization, nucleic acid interaction and photoluminescent properties of (E)-furan-2-yl(2-(2-hydroxybenzylidene)hydrazinyl) methaniminium and its Mn(II), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes

Cited by 11 publications

References 37 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

Binuclear Co(II), Ni(II) and Cu(II) Complexes of a new Bis(tridentate) Hydrazone Ligand: Synthesis, Thermal, Spectroscopic, Biological, Molecular Docking and Theoretical Studies

Crystal structure ofN′-[4-(dimethylamino)benzylidene]furan-2-carbohydrazide monohydrate

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