Concise Preparation of Optically Active Heteroaryl α-(Hydroxyamino) Esters

International audienc

Brønsted Acid Catalyzed Bisindolization of α-Amido Acetals: Synthesis and Anticancer Activity of Bis(indolyl)ethanamino Derivatives

A brønsted acid-catalyzed bisindolization reaction with suitable α-amido acetals is reported, which tolerates a wide range of indoles. The method rapidly accesses the biologically relevant bisindolyl ethanamine scaffold in good to excellent yields upon mild amide basic hydrolysis. In preliminary pharmacological studies, some of these compounds reveals cytotoxic activity in U937 cancer cells. The marine natural alkaloid 2,2-di(6’-bromo-3’-indolyl)-ethylamine was the most active compound and could be a good lead candidate for further optimization. For the first time, the biological role of this brominated bisindole marine alkaloid is presented