ABSTRACT Perfluorophenyl BODIPY–quinoline conjugates ( 8–10 ) were synthesized via post‐functionalization of BODIPY. The nucleophilic aromatic substitution (S N Ar) of pentafluorophenyl–dipyrromethane (PFP–DPM) was obtained in a nearly quantitative yield under tetrahydrofuran reflux. Subsequently, the perfluorophenyl BODIPY precursor ( 3 ) was condensed with quinoline‐4‐carboxylic acids ( 5–7 ). The condensation of BODIPY and quinolines was performed through Steglich esterification, yielding up to 88% of the product. Spectroscopic analyses confirmed that the resulting conjugates retained the electronic absorption and emission characteristics of BODIPY, highlighting their potential for fluorescence labeling in the visible region. However, fluorescence quenching was observed in polar solvents due to non‐radiative processes. Molecular docking studies revealed that all conjugates interacted with the catalytic residue of cyclin‐dependent kinase 6 (CDK6). Furthermore, conjugation with BODIPY improved the binding similarity of quinoline derivatives ( 5 and 6 ) to the target protein, highlighting the potential for selective CDK6 targeting.
Firmansyah et al. (Sun,) studied this question.