Synthesis and anticancer activities of ageladine A and structural analogs

A series of ageladine A analogs that include 2-aminoimidazo[4,5-c]azepines (seven-membered rings) and 2-amino-3H-imidazo[4,5-c]pyridine (six-membered rings) derivatives were synthesized and evaluated for their anticancer effects against several human cancer cell lines and MMP-2 inhibition in vitro. Only compounds possessing the aromatic azepine (seven-membered ring) core showed anticancer activity with IC50 values in the low micromolar range.

Graphical abstractA series of ageladine A and structurally related aromatic azepine analogs have been synthesized and evaluated for anticancer activity. The key steps involve a Pictet–Spengler cyclocondensation and oxidative aromatization.Figure optionsDownload full-size imageDownload as PowerPoint slide