Research Article | Volume: 4, Issue: 6, June, 2014

Exploring the Synthesis of New 1-(4-Substitutedphenylamino) imidazo[1,5-a]indol-3-one Derivatives as Cyclized Analogs of Leucettines

Guillaume Burgya b Emmanuelle Limantona François Carreauxa Emilie Durieub Laurent Meijerb and Jean-Pierre Bazureaua   

Open Access   

Published:  Jun 28, 2014

DOI: 10.7324/JAPS.2014.40604

New 1-arylaminoimidazo[1,5-a]indol-3-ones were synthesized as cyclized derivatives of leucettine L41, a low molecular weight inhibitor of the DYRKs/CLKs protein kinases with potential applications in Alzheimer's disease and Down syndrome. In this first approach, access to the desired 1-aminoimidazo[1,5-a]indol-3-ones involved 5 steps and was explored with a series of various primary amines and polar secondary amines in order to introduce molecular diversity on N-1 position. The 5 step synthesis of the 1-arylaminoimidazo[1,5-a]indol-3-ones was achieved and the limiting step of this process was the final cyclization via a sulphur/nitrogen displacement from methylsulfanyl thiourea intermediates. Good results were obtained for isothioureas derived from primary amines. The 1-arylaminoimidazo[1,5-a]indol-3-ones were evaluated on a panel of five protein kinases (DYRK1A, CK1, CDK5/p25, GSK3α/β and CLK1).

Keyword:     Imidazo[15-A]Indol-3-One thiourea isothiorurea intramolecular sulphur/ nitrogen displacement protein kinase DYRKs CLKs Leucettines.


Jean-Pierre BAZUREAU., Exploring the Synthesis of New 1-(4- Substitutedphenylamino) imidazo[1,5-a]indol-3-one Derivatives as Cyclized Analogs of Leucettines. J App Pharm Sci, 2014; 4 (06): 025-032.

Copyright:The Author(s). This is an open access article distributed under the Creative Commons Attribution Non-Commercial License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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