Synthesis, Photophysical Characterization, and Anticancer Evaluation of Novel Furochromene Derivatives

A series of novel furochromen derivatives, namely (2E)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-arylprop-2-en-1-ones 4a-c, were synthesized via the Knoevenagel condensation of 6-hydroxy-4,7-dimethoxybenzofuran-5-ylethanone 2 with various aromatic aldehydes. Molecular structures were fully established using ultraviolet-visible spectroscopy (UV-vis), fourier transform infrared (FTIR), Mass Spectrometry, and nuclear magnetic resonance (NMR) techniques. The photophysical characteristics of the compounds were systematically studied in various solvents at 298 K., revealing significant solvatochromic behavior and fluorescence emission, suggesting their potential as fluorescent probes for biological imaging. In addition, quantum chemical calculations discrete fourier transform (DFT)/B3LYP) were performed to determine highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energies and dipole moments in both ground and excited states. To assess their biological relevance, the synthesized compounds were tested for their antiproliferative activity against human cancer cell lines A549 (lung), HepG2 (liver), and HCT-116 (colon), using real-time cell impedance spectroscopy. Among the tested molecules, compound 4c showed the most potent cytotoxic effect, with complete inhibition of cell viability in A549 and HepG2 cells and an IC50 of 4.6 µM against A549. These findings highlight the dual potential of furochromene derivatives as both photophysical tools and promising anticancer candidates.