Synthesis, Crystal Structure and Cytotoxic Activity of a New NAN-190 Analogue

摘要

The NAN-190 analogue 2-(2-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethoxy)ethyl)isoindoline-1,3-dione(1, C23H27N3O4, Mr = 409.48) was synthesized via a three-step reaction and characterized by 1H NMR, 13 C NMR, ESIMS and single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pna21 with a = 7.6445(15), b = 38.851(8), c = 7.1316(14) A, V = 2118.0(7) A3, Z = 4, Dc = 1.2840 mg/mm3, μ = 0.089 mm-1, F(000) = 872.4, R = 0.0545 and w R = 0.1681. The single-crystal X-ray structural analysis reveals that the piperazine ring in compound 1 presents a stable and minimum energy chair conformation. In addition, the preliminary cytotoxic assay shows that the title compound exhibits strong and selective inhibitory activity against DU145 cells(IC50 = 5.88 ± 1.02 μM).