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

TETRAHEDRON

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Article

Zeghada, Sarah^1,2,3  Bentabed-Ababsa, Ghenia²  Mongin, Olivier¹  Erb, William¹  Picot, Laurent⁴  Thiery, Valerie⁴  Roisnel, Thierry¹  Dorcet, Vincent¹  Mongin, Florence¹ 

[1] Univ Rennes, ISCR Inst Sci Chim Rennes, CNRS, UMR 6226, F-35000 Rennes, France

[2] Univ Oran 1 Ahmed Ben Bella, Fac Sci Exactes & Appl, Lab Synth Organ Appl, BP 1524, El Mnaouer 31000, Oran, Algeria

[3] Ecole Super Genie Elect & Energet Oran ESGEE, BP CH 2,Technopole USTO, Oran 2, Algeria

[4] Univ La Rochelle, UMRi CNRS 7266, Lab Littoral Environm & Soc, F-17042 La Rochelle, France

关键词: Acridine;    Acridone;    N-arylation;    Copper;    Antiproliferative activity;    Melanoma cells;   

DOI  :  10.1016/j.tet.2020.131435

来源: Elsevier

【 摘 要 】

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. (C) 2020 Elsevier Ltd. All rights reserved.

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