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

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-io...

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Bibliographic Details
Published in:Tetrahedron 2018-04, Vol.74 (15), p.1785-1801
Main 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
Format: Article
Language:English
Subjects:
Acridin
Antiproliferative activity
Chemical Sciences
Copper
Isatin
Kinase inhibition
Medicinal Chemistry
Melanoma cells
N-arylation
Organic chemistry
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.02.038