2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities. Issue 15 (12th April 2018)

• Record Type: Journal Article
• Authors: Brikci-Nigassa, Nahida Mokhtari; Bentabed-Ababsa, Ghenia; Erb, William; Chevallier, Floris; Picot, Laurent; Vitek, Lucille; Fleury, Audrey; Thiéry, Valérie; Souab, Mohamed; Robert, Thomas; Ruchaud, Sandrine; Bach, Stéphane; Roisnel, Thierry; Mongin, Florence
• Is Part Of: Tetrahedron. Volume 74:Issue 15(2018)
• Page Start: 1785
• Page End: 1801
• Publication Date: 2018-04-12
• Subjects: Isatin -- Acridin -- N-arylation -- Copper -- Kinase inhibition -- Antiproliferative activity -- Melanoma cells; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.02.038
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Because N -arylation of isatin only worked with iodoferrocene (and in low yield), we employed N -arylation of 2-aminophenones and subsequent oxidative cyclization to access various N -arylated isatins. In the course of this work, we observed that N -arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but to (benzo)furo- and (benzo)thieno[2, 3- b ]quinolines. Separate cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds. Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells, and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β, Haspin and leishmanial CK1. The biological results are reported. Graphical abstract: