Synthesis of 2-(4-phenylthiazol-2-yl)-benzo[de]isoquinoline-3,1-dione Derivatives as Potential Anticancer Agents

Abstract

Background and Objective: In light of recent research on thiazole derivatives and their demonstrated biological activities, this study was undertaken to synthesize 2-(4-phenylthiazol-2-yl)-benzo[de]isoquinoline-3,1-dione derivatives as apoptosis-inducing compounds with potential anticancer effects. Accordingly, the main objective was to prepare and evaluate these derivatives as possible anticancer agents.

Materials and Methods: For the synthesis of compounds (4a–4j), 1 mmol of 4-phenylthiazol-2-amine derivatives was reacted with 198.1 mg (1 mmol) of naphthalic anhydride in a 25 mL round-bottom flask. Then, 101.1 mg (1 mmol) of triethylamine was added, and the mixture was refluxed in toluene for 24 hours. The reaction progress was monitored by TLC, confirming completion. The mixture was filtered, the solvent was removed under reduced pressure, and a 50:50 mixture of water and ethyl acetate was added. The organic phase was discarded, and the final derivatives were isolated by standard work-up.

Results: In this study, derivatives 4a–4j were successfully synthesized and evaluated as apoptosis inducers with potential anticancer activity.

Conclusion: In the search for new molecules with anticancer potential, isoquinoline and thiazole derivatives have been identified as promising scaffolds. In addition to their reported antifungal and antibacterial effects, these compounds display cytotoxic properties, supporting their potential role in anticancer drug discovery.