Synthesis, Crystal Structure, and Antitumor Activity of 1-(4-Methoxybenzylidene)-2-(1-phenyl-6-trifluoromethyl-1H-pyr azolo[3,4-d]pyrimidin-4-yl)hydrazine Monohydrate

The novel title compound 1-(4-methoxybenzylidene)-2-(1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)hydrazine monohydrate (C20H15F3N6O center dot H2O, M-r = 430.40) has been synthesized by a four-step procedure including the cyclization, chlorination, hydrazinolysis and condensation reaction, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pbca with a = 8.3779(13), b = 17.607(3), c = 26.774(4) angstrom, V= 3949.2(11) angstrom(3), Z = 8, D-c = 1.448 g/cm(3), mu = 0.117 min(-1), F(000) = 1776, the final R = 0.0553 and wR = 0.1516 for 2354 observed reflections with I > 2 sigma(I). X-ray diffraction analysis reveals that the title compound is almost coplanar except for the trifluoromethyl and phenyl moieties. In the crystal packing, the molecules are linked by intermolecular O(1W)-H(1WA)center dot center dot center dot N(2), O(1W)-H(1WA)center dot center dot center dot N(4) and N(5)-H(5A)center dot center dot center dot O(1W) hydrogen bonds via water molecules and stacked through pi-pi stacking interactions. The preliminary bioassay suggested that the title compound exhibits relatively good antitumor activity against HepG2 and BCG-823.