Abstract Design, synthesis and anticancer activity of a series of imine-pyrazolopyrimidinones is reported for the first time. Compounds 9d, 9n and 9o in the series show encouraging in vitro anticancer activity with low micromolar IC 50 values against prostate (PC3) and breast (MCF7) cancer cell lines. Some notions about structure–activity relationships and plausible mechanism of biological activity are presented.