N′-[5-(4-Nitrophenyl)furan-2-ylmethylidene]-N,N-diphenylhydrazine

In the crystal structure of the title compound, C26H22N4, the molecule is located on an inversion centre and shows an E configuration with respect to each C=N bond. The dihedral angle between the phenyl rings in the diphenylhydrazone group is 83.69 (11)°. These two rings make dihedral angles of 30.53 (15) and 84.53 (16)° with the central N—N=C—C=N—N dihydrazonoethane plane. Intermolecular C—H⋯π interactions are observed.

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Potential Amoebicidal Activity of Hydrazone Derivatives: Synthesis, Characterization, Electrochemical Behavior, Theoretical Study and Evaluation of the Biological Activity

Toledano-Magaña

García‐Ramos

Navarro-Olivarria

et al. 2015

Molecules

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Four new hydrazones were synthesized by the condensation of the selected hydrazine and the appropriate nitrobenzaldehyde. A complete characterization was done employing 1 H-and 13 C-NMR, electrochemical techniques and theoretical studies. After the characterization and electrochemical analysis of each compound, amoebicidal activity was tested in vitro against the HM1:IMSS strain of Entamoeba histolytica. The results showed the influence of the nitrobenzene group and the hydrazone linkage on the amoebicidal activity. meta-Nitro substituted compound 2 presents a promising amoebicidal activity with an IC50 = 0.84 μM, which represents a 7-fold increase in cell growth inhibition potency with respect to metronidazole (IC50 = 6.3 μM). Compounds 1, 3, and 4 show decreased amoebicidal activity, with IC50 values of 7, 75 and 23 µM, respectively, as a function of the nitro group position on the aromatic ring. The observed differences in the biological activity could be explained not only by the redox potential of the molecules, but also by their capacity to participate in the formation of intra-and intermolecular hydrogen bonds. Redox potentials as well as the amoebicidal activity can be described with parameters obtained from the DFT analysis.

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N′-[5-(4-Nitrophenyl)furan-2-ylmethylidene]-N,N-diphenylhydrazine

Cited by 3 publications

References 11 publications

Synthesis, characterization and evaluation of the substituent effect on the amoebicide activity of new hydrazone derivatives

Synthesis, characterization and evaluation of the substituent effect on the amoebicide activity of new hydrazone derivatives

(1E,2E)-1,2-Bis(2,2-diphenylhydrazin-1-ylidene)ethane

Potential Amoebicidal Activity of Hydrazone Derivatives: Synthesis, Characterization, Electrochemical Behavior, Theoretical Study and Evaluation of the Biological Activity

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