6533b82bfe1ef96bd128d4d3

RESEARCH PRODUCT

Synthesis of bis(indolylmaleimide) macrocycles

Herwig PongratzAlfred PoppSiavosh MahboobiIrene DechantDieter SchollmeyerHans Reindl

subject

Bis-indolylmaleimideChemistryIntramolecular forceOrganic ChemistryIntermolecular forceNucleophilic substitutionMedicinal chemistry

description

The synthesis of a novel class of macrocyclic bis(indolylmaleimides) is reported. The key step involves the intermolecular connection of 2,2′-bridged indoles with 3,4-dibromo-2,5-dihydro-1H-2,5-pyrroledione (dibromomaleimide) derivatives. The bis(indolylmaleimides) afforded by this method were further processed by intramolecular nucleophilic substitution of the remaining bromo substituents forming flexible N-substituted macrocycles (9a-9j, 10a-10e) and, by connecting both maleimides, semi rigid macrocycles (7a-7xx).

https://doi.org/10.1002/jhet.5570370215