Anti-tyrosinase and Anti-butyrylcholinesterase Quinolines-Based Coumarin Derivatives: Synthesis and Insights from Molecular Docking Studies

In this work, a series of anti-tyrosinase and anti-butyrylcholinesterase coumarin derivatives 4a–f and 5a–f were synthesized starting from 4-hydroxycoumarin. The condensation of 2-(arylimin)-4-hydroxycoumarins 3a–f with dimethylformamide dimethyl acetal (DMF-DMA), used as a key reaction, afforded the precursors 4a–f, whose acid treatment led to the formation of 5a–f. These prepared heterocycles were characterized by spectroscopic means including (1)H-NMR, (13)C-NMR, and DCI-HRMS. Their anti-tyrosinase and anti-butyrylcholinesterase activities have been evaluated in vitro and some of them exhibited promising activity supported by the molecular docking analysis to estimate possible interactions between these compounds and active sites of both proteins tyrosinase (PDB: 2Y9W) and butyrylcholinesterase (PDB: 4TPK).