6127-33-9Relevant academic research and scientific papers
Investigation of a Late-Stage Derivatization Approach to Isatogens: Discovery of New Reaction Pathways
Edeson, Steven J.,Maduli, Elvis J. M.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.
, p. 83 - 86 (2016/01/26)
We have developed a new strategy for preparing 2-substituted indolone N-oxides (isatogens) by substitution reactions with aryl- and alkyl-organometallic reagents. This approach allows a range of substituents to be incorporated at a late stage and complements existing methods that necessitate their early stage incorporation during substrate preparation. Further chemistry has been found to take place at the nitrone moiety; intramolecular dipolar cycloaddition provides access to angularly fused tricyclic heterocycles. More unusually however, these compounds are prone to further addition by organozinc reagents leading to 2,2-disubstituted 3-oxindole products.
2-Iodoisatogens: Versatile intermediates for the synthesis of nitrogen heterocycles
Maduli, Elvis J. M.,Edeson, Steven J.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.
supporting information, p. 390 - 392 (2015/01/30)
A Cu-promoted cyclization of 2-nitrophenyl iodoacetylenes provides a direct route to a range of 2-iodoisatogens. These compounds represent useful intermediates for the late-stage elaboration of the C-I bond to furnish isatins and a range of alternative heterocyclic products.
2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
Najahi, Ennaji,Valentin, Alexis,Fabre, Paul-Louis,Reybier, Karine,Nepveu, Fran?oise
, p. 269 - 274 (2014/04/17)
The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy- indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC 50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
