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Keywords = pyrroloindoles

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11 pages, 2109 KiB  
Article
Pyrroloindole-Based Dynamic Combinatorial Chemistry
by Tiberiu-Marius Gianga, Dora-Maria Răsădean and G. Dan Pantoș
Symmetry 2020, 12(5), 726; https://doi.org/10.3390/sym12050726 - 3 May 2020
Cited by 3 | Viewed by 3203
Abstract
We report a new class of building blocks for Dynamic Combinatorial Chemistry (DCC) based on the pyrroloindole scaffold. The attachment of l-cysteine on the α, α′ positions of the core makes the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries [...] Read more.
We report a new class of building blocks for Dynamic Combinatorial Chemistry (DCC) based on the pyrroloindole scaffold. The attachment of l-cysteine on the α, α′ positions of the core makes the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries (DCLs). The synthesis of the core follows a modified version of the Knoevenagel–Hemetsberger approach. The new building block (l-PI) is fluorescent (Φ = 48%) and relatively stable towards thermal and photodegradation. The chirality of the cysteine is transferred to the electron-rich pyrroloindole core. Homo- and heterochiral DCLs of l-PI with electron-deficient l- and d-naphthalenediimide (NDI) lead to similar library distributions regardless of the enantiomer used. When no salt is present, the major component is a dimer, while dimers and tetramers are obtained at increased ionic strength. Full article
(This article belongs to the Special Issue Symmetric and Asymmetric Structure in Drug Design and Biomolecules)
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