2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities. Issue 38 (18th September 2020)

• Record Type: Journal Article
• Authors: Zeghada, Sarah; Bentabed-Ababsa, Ghenia; Mongin, Olivier; Erb, William; Picot, Laurent; Thiéry, Valérie; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence
• Is Part Of: Tetrahedron. Volume 76:Issue 38(2020)
• Publication Date: 2020-09-18
• Subjects: Acridine -- Acridone -- N-arylation -- Copper -- Antiproliferative activity -- Melanoma cells; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131435
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: Image 1