RESUMO
Four new hydrazones were synthesized by the condensation of the selected hydrazine and the appropriate nitrobenzaldehyde. A complete characterization was done employing 1H- and 13C-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.
Assuntos
Amebicidas/farmacologia , Benzaldeídos/química , Entamoeba histolytica/efeitos dos fármacos , Hidrazinas/química , Hidrazonas/farmacologia , Nitrobenzenos/química , Amebicidas/síntese química , Técnicas Eletroquímicas , Hidrazonas/síntese química , Ligação de Hidrogênio , Concentração Inibidora 50 , Metronidazol/farmacologia , Oxirredução , Teoria Quântica , Relação Estrutura-AtividadeRESUMO
The title compound, C19H15N3O2, shows an E conformation of the imine bond. The dihedral angle between the planes of the phenyl rings in the di-phenyl-hydrazine groups is 88.52â (4)°. The 2-nitro-benzene ring shows a torsion angle of 10.17â (8)° with the C=N-N plane. A short intra-molecular C-Hâ¯O contact occurs. In the crystal, only van der Waals contacts occur between the mol-ecules.
RESUMO
The asymmetric unit of the title compound, C17H14N2S, consists of two crystallographically independent mol-ecules with similar conformations. The dihedral angles between the phenyl rings are 89.32â (5) and 82.80â (5)° in the two mol-ecules. In the crystal, mol-ecules are linked by C-Hâ¯π inter-actions, forming a three-dimensional network.
RESUMO
In the crystal of the title compound, C19H14N4O4, the asymmetric unit consists of two discrete mol-ecules. The C=N bonds in both mol-ecules show an E conformation. The dihedral angles between the C atoms of the 2,4-dinitrobenzene rings and the C=N-N planes are 13.52â (9) and 13.82â (9)° for the two mol-ecules. In the crystal, C-Hâ¯O hydrogen bonds, mainly between the phenyl ring and the nitro group along the b axis.
RESUMO
In the title compound, C23H17N3O3, the terminal benzene rings are oriented at dihedral angles of 3.67â (7), 76.02â (7) and 16.37â (7)° with respect to the central furan ring. In the crystal, mol-ecules are connected via weak C-Hâ¯O hydrogen bonds, resulting in a three-dimensional supra-molecular array.
RESUMO
The asymmetric unit of the title compound, C(19)H(15)N(3)O(2), contains two mol-ecules, both of which show an E conformation of the imine bond. The dihedral angles between the phenyl rings in the phenyl-hydrazine groups are 86.09â (6) and 83.41â (5)° in the two mol-ecules. The 4-nitrobenzene rings show torsion angles of 4.4â (2) and 10.9â (2)° from the two C=N-N planes. In the crystal, C-Hâ¯π inter-actions and C-Hâ¯O hydrogen bonds are observed growing along the a, b and c axes, resulting in a complex supramolecular array.