Synthesis and Anticancer Activity of 3,4-Diaryl-1,2-dihydro- and 1,2,3,4-Tetrahydroquinolines

Abstract

Tetrahydroquinolines are key structures in a variety of natural products with diverse pharmacological utilities and other applications. A series of 3,4-diaryl-5,7-dimethoxy-1,2,3,4-tetrahydroquinolines were synthesized in good yield by reacting 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones with different Grignard reagents followed by the dehydration of the intermediate phenolic compounds. Subsequent reduction and deprotection were carried out to achieve the desired tetrahydroquinolone moiety. The lead compound 3c showed low micromolar inhibition of various cancer cell lines. Demethylation under different reaction conditions was also investigated to afford the corresponding monohydroxy analogues.

Keywords

• tetrahydroquinolines
• dihydroquinolin-4-ones
• quinolones
• Grignard reactions
• dehydration
• hydrogenation