2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities

Sarah Zeghada (1, 2, 3) , Ghenia Bentabed-Ababsa (2) , Olivier Mongin (1) , William Erb (1) , Laurent Picot (4) , Valérie Thiéry (4) , Thierry Roisnel (1) , Vincent Dorcet (1) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Université d'Oran 1 Ahmed Ben Bella [Oran]
3 USTO MB - Université des sciences et de la Technologie d'Oran Mohamed Boudiaf [Oran]
4 LIENSs - LIttoral ENvironnement et Sociétés

By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse to a lithium-zinc base and converted to the corresponding 4-iodo derivative, which was involved in copper-catalyzed couplings with pyrrolidinone and pyrazole. Finally, addition of pyrazole, indole and carbazole onto the 9 position of bare acridine was improved. While moderate biological activity was noticed in melanoma cells growth inhibition, the newly prepared compounds feature interesting photophysical properties which were evaluated in a preliminary study.

Mots clés: Acridine; Acridone; N-arylation; Copper; Antiproliferative activity; Melanoma cells

Domaines: Chimie organique

Sarah Zeghada, Ghenia Bentabed-Ababsa, Olivier Mongin, William Erb, Laurent Picot, et al.. 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities. Tetrahedron, 2020, 76 (38), pp.131435. ⟨10.1016/j.tet.2020.131435⟩. ⟨hal-03302141⟩