Chalcone-Mediated and unexpected rearrangement preparation of 1H-pyrazol-furo[2,3-d]pyrimidine derivatives as potent antitumor agents

The versatility of N-heterocyclic rings is the focus of most attention because of their remarkable biological activities. In this study, a new chalcone-mediated and unexpected rearrangement reaction has been explored for the preparation of 1H-pyrazol-furo[2,3-d]pyrimidines 5a-5r. The purities of compounds 5a-5r were analyzed via ultra-performance liquid chromatography, and their structures were elucidated by NMR, and HRMS. Additionally, the molecular structure of 5d was further confirmed by X-ray structure analysis. In vitro, the inhibitory activities of 5a-5r were tested against HepG2 cell lines by the CCK8 procedures. The IC₅₀ values of 0.17 - 69.89 μmol/L indicated the potential antitumor effectiveness of target compounds 5a-5r. Furthermore, compound 5c was selected to induce HepG2 cells apoptosis and conduct docking study, which considered as a new targeted antitumor agent.