167631-20-1Relevant articles and documents
Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class
Neagoie, Cleopatra,Vedrenne, Emeline,Buron, Frédéric,Mérour, Jean-Yves,Rosca, Sorin,Bourg, Stéphane,Lozach, Olivier,Meijer, Laurent,Baldeyrou, Brigitte,Lansiaux, Amelie,Routier, Sylvain
experimental part, p. 379 - 396 (2012/04/10)
A library of substituted chromeno[3,4-b]indoles was developed as Lamellarin isosters. Synthesis was achieved from indoles after a four-step pathway sequence involving C-3 iodination, a Suzuki cross-coupling reaction, and a one pot deprotection/lactonisation step. Twenty final compounds were tested in order to determine their activity against topoisomerase I and kinases, the two major biological activities of Lamellarins. One newly synthesized derivative exhibited a strong topoisomerase activity comparable to reference compounds such as campthotecin and Lamellarin with only a weak kinase inhibition. Two other lead compounds were identified as new nanomolar DYRK1A inhibitors and several other drugs affected the kinases in the sub-micromolar range. These results will enable us to use the chromeno[3,4-b]indole as a pharmacophore to develop potent treatments for neurological or oncological disorders in which DYRK1A is fully involved.
Synthesis of indolobenzazepinones by application of an isocyanide-based multicomponent reaction
Beaumont, Stephane,Retailleau, Pascal,Dauban, Philippe,Dodd, Robert H.
scheme or table, p. 5162 - 5175 (2009/05/07)
Application of a Ugi multicomponent reaction to oxo acids 4 allows the formation of potentially antimitotic indolobenzazepinones of type 5 in good yields of up to 72%, whereas the same transformation from the starting substrate 6 gives access to analogues of paullone with yields of up to 89%. The reaction could be applied to a wide range of isocyanides, thereby ensuring introduction of molecular diversity at the key C-5 position. Use of cyclohexenyl isocyanide allows post-condensation modifications, while careful choice of the amine and the indole protecting groups proved to be important for providing the deprotected compounds necessary for biological tests. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
