2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities - Université de Rennes Access content directly
Journal Articles Tetrahedron Year : 2018

2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities

William Erb
Valérie Thiéry

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.
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Dates and versions

hal-01774406 , version 1 (29-05-2018)

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Nahida Mokhtari Brikci-Nigassa, Ghenia Bentabed-Ababsa, William Erb, Floris Chevallier, Laurent Picot, et al.. 2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities. Tetrahedron, 2018, 74 (15), pp.1785-1801. ⟨10.1016/j.tet.2018.02.038⟩. ⟨hal-01774406⟩
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