4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]-N′-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide dimethyl sulfoxide monosolvate

The molecular structure of the title compound, C26H18N4O6S·C2H6OS, shows an E conformation of the hydrazone double bond. The presence of a methylene group between the benzo[de]isoquinoline and benzenesulfonyl moieties allows the 4-nitrophenyl ring and the benzo[de]isoquinoline system to be parallel with respect to each other, so that the molecule adopts a U-shaped spatial conformation. The dihedral angle between mean planes of these aromatic groups is 4.4 (1)°. This special arrangement enables neighboring molecules to be intercalated, forming slipped π–π interactions [centroid–centroid distance = 3.535 (2) Å] between the 4-nitrophenyl and benzo[de]isoquinoline groups and point-to-face C—H⋯π interactions between the benzo[de]isoquinoline and benzenesulfonyl aromatic systems. In addition, the crystal packing also features an intermolecular N—H⋯O interaction involving the amine group and the dimethyl sulfoxide solvent molecule.

The authors thank CAPES and CNPq for financial support.  (Rollas et al. 2002, Frlan et al. 2008, analgesic (Lima et al. 1999, Sondhi et al. 2006, etc. Sulfonyl-hydrazones was selective inhibitor of p110α, a phosphoinositide-3-kinase that is over-expressed in 30% of tumors (Kendall et al. 2007). In innovative study, the sulfonyl-hydrazones were reported by enhance myocardial repair by stem cells by activating cardiac differentiation in human mobilized peripheral blood mononuclear cells (M-PBMCs) (Sadek et al. 2008).
Cyclic imides have also many therapeutic properties including antibacterial, antitumor, diuretic and antiviral (Cechinel Filho et al. 2003). In a previous publication, we reported the synthesis of imidobenzenesulfonyl compounds that showed promising analgesic profiles in the acetic acid-induced mice writhing test. The mechanism of action occurred possibly due to additional non-covalent interactions with the COX active site (Walter et al. 2002). The naphthalimides, in special,  (Suárez et al. 1992). Recently, many similar compounds have been showed activity against different cancer cell lines (Ingrassia et al. 2009, Wu et al. 2009, Norton et al. 2008).
The title compound (I) (Scheme 1) was synthesized as a part of our work to investigate the antitumoral activity of the sulfonyl-hydrazones cyclic imides derivatives , Silva et al. 2006).
The molecular structure of the title compound ( Fig. 1) shows E conformation on the hydrazone double bond, which is evidenced by the torsion angle S1-N2-N3-C21 of 165.8 (2)°. The presence of a methylene group among benzo [de]isoquinoline and benzenesulfonyl moieties allows p-nitrophenyl ring and benzo[de]isoquinoline system to be parallel with respect to each other, so that the molecule adopts an U-shaped spatial conformation. The dihedral angle between mean planes of these planar groups is 4.4 (1)°. This special arrangement enables the neighboring molecule be intercalated by a center of symmetry, forming pairs of molecules in a centrosymmetric structure (Fig. 2). Slipped π-π interaction between p-nitrophenyl and benzo[de]isoquinoline, with centroid-C12 distance of 3.589 Å, and point-to-face C-H···π interaction between benzenesulfonyl and benzo [de]isoquinoline aromatic systems, with centroid-H8 distance of 2.903 Å, are observed.
In addition, crystal packing also shows an intermolecular N2-H···O1S interaction involving amine group and DMSO solvate. as described for similar compounds (Silva et al. 2006. The reaction was carried out by stirring at room temperature for one hour. The solid was filtered off with suction. The crystal used for data collection was obtained by dissolving 30 mg of (I) in 10 ml of dimethylsulfoxide and by slow evaporation of the solvent.
supplementary materials sup-2 Refinement All non-H atoms were refined with anisotropic displacement parameters. H atoms were placed at their idealized positions with distances of 0.93 and 0.97 Å and U eq fixed at 1.2 times U iso of the preceding atom for C-H Ar and C-H 2 , respectively and at 1.5 times U iso of the preceding atom for C-H 3 . The H atom of the amino group was found from Fourier map and treated with riding model and its U eq was refined freely. Fig. 1. The molecular structure of the title compound with the labelling scheme. Displacement ellipsoids are shown at the 40% probability level.