1072107-19-7Relevant academic research and scientific papers
Convenient Synthesis of Alternatively Bridged Tryptophan Ketopiperazines and Their Activities against Trypanosomatid Parasites
Cockram, Peter E.,Turner, Callum A.,Slawin, Alexandra M. Z.,Smith, Terry K.
, (2022/01/11)
There is an urgent need for the development of new treatments against trypanosomatid parasites; the causative agents of some of the most debilitating diseases in the developing world. This work targets an interesting 6-5-6-6 fused carboline scaffold, accessing a range of substituted derivatives through stereospecific intramolecular Pictet–Spengler condensation. Modification of the cyclisation conditions allowed retention of the carbamate protecting group and gave insight into the reaction mechanism. Compounds’ bioactivities were measured against T. brucei, T. cruzi, L. major and HeLa cells. We have identified promising pan-trypanocidal lead compounds based on the core scaffold, and highlight key SAR trends which will be useful for the future development of these compounds as potent trypanocidal agents.
Synthesis of novel indole-based ring systems by acid-catalysed condensation from α-amino aldehydes and L-Trp-OMe
Gomez-Monterrey, Isabel M.,Campiglia, Pietro,Bertamino, Alessia,Aquino, Claudio,Mazzoni, Orazio,Diurno, Maria V.,Iacovino, Rosa,Saviano, Michele,Sala, Marina,Novellino, Ettore,Grieco, Paolo
experimental part, p. 1983 - 1992 (2009/04/03)
Acid-catalysed condensation of tryptophan with different α-amino aldehyde derivatives has been explored as a useful route to the synthesis of novel amino acid derived heterocycles and peptidomimetic scaffolds. By this approach, compounds containing a tetrahydro-β-carboline and a novel octahydropyrrolo[ 3′,2′:3,4]pyrrolo[2,3-b]indole system have been efficiently synthesized. Here we report the characterization of these new compounds and preliminary studies of the reactivity of the tetrahydro-β- carboline system. Wiley-VCH Verlag GmbH & Co. KGaA.
