0000000000147428
AUTHOR
Alfred Popp
Synthesis of pyrrolo[3′,4′:2,3]azepino[4,5,6-cd]indole-8,10-diones
3-Amino-4-(3-indolyl)pyrrolin-2,5-diones are condensed with various aldehydes and ketones to the cor responding imines. Under Pictet-Spengler conditions, the latter do not cyclize to pyrrolo-β-carbolines, but readily yield pyrrolo[3′,4′:2,3]azepino[4,5,6-cd]indole-8,10-diones.
Synthesis of bis(indolylmaleimide) macrocycles
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).
Synthesis of Pyrrolidin-2-ones and of Staurosporine Aglycon (K-252c) by Intermolecular Michael Reaction
Indolo[2,3-a]pyrrolo[3,4-c]carbazoles were isolated from nature, e.g., from low plants, especially fungi, as structurally rare natural substances. Responsible for naming and also the most important representative of this type is staurosporine (1), isolated from Streptomyces staurosporeus, and its aglycon (2), also known as staurosporinone or K-252c. 3,4-Disubstituted pyrrolidin-2-ones, a group of compounds with many interesting biological properties are related to staurosporinone. The most important property is the inhibition of protein kinase C (PKC), so that this antiproliferative agent can interfere with the cell cycle. The synthetic strategy, developed by us, allows the synthesis of pyr…
ChemInform Abstract: Synthesis of Pyrrolidin-2-ones and of Staurosporine Aglycon (K-252c) by Intermolecular Michael Reaction.
Indolo[2,3-a]pyrrolo[3,4-c]carbazoles were isolated from nature, e.g., from low plants, especially fungi, as structurally rare natural substances. Responsible for naming and also the most important representative of this type is staurosporine (1), isolated from Streptomyces staurosporeus, and its aglycon (2), also known as staurosporinone or K-252c. 3,4-Disubstituted pyrrolidin-2-ones, a group of compounds with many interesting biological properties are related to staurosporinone. The most important property is the inhibition of protein kinase C (PKC), so that this antiproliferative agent can interfere with the cell cycle. The synthetic strategy, developed by us, allows the synthesis of pyr…
ChemInform Abstract: Synthesis of Bis(indolylmaleimide) Macrocycles
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).