A novel potential anticancer chalcone: synthesis, crystal structure and cytotoxic assay

Abstract

Recently, a wide number of bioactivities has been discovered for chalcones. These applications depend on structural features such as planarity, electronic delocalization paths and substitution pattern on aromatic rings. This work aimed the structural analysis of a novel nitroaminochalcone (C15H12N2O3, NAC) through single crystal X-ray diffraction technique and assessment of its cytotoxicity against tumor cells. NAC is almost completely planar, as evidenced by the low angle formed between its phenyl rings [4.40 (12)°], which enables the π-electron delocalization through whole molecule. A resonance-assisted hydrogen bond (RAHB) is another interesting intramolecular feature of NAC, which is assembled between the amino and carbonyl groups into a cyclic S (6) motif. The crystal packing is featured by the formation of dimers stabilized by a (16) motif engaging the carbonyl group and nitrobenzene. These dimers are organized in a 2D layer onto (010) through Csingle bondH⋯O interactions involving the nitro e amine groups in a motif. Furthermore, Hirshfeld surface analysis showed the crystal packing of NAC is also stabilized by both Csingle bondH⋯π and π⋯π interactions. The compound showed high cytotoxicity against human tumor cells.