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Desymmetrization Reactions of Indigo with Grignard Reagents for the Synthesis of Selective Antiplasmodial [1H,3′H]‑3-Aryl-2,2′- diindol-3′-ones

Butler, Nicholas M; Bremner, John B; Willis, Anthony; Lucantoni, Leonardo; Avery, Vicky M; Keller, Paul


The nucleophilic addition of organomagnesium and organolithium species to the cheap and robust natural dye indigo led to desymmetrization of the heterocyclic nucleus via a Grignard addition−dehydration procedure. Twenty-seven diversely functionalized [1H,3′H]-3-substituted 2,2′-diindol-3′-ones were synthesized by this methodology, with several showing submicromolar inhibition and exquisite selectivity against P. falciparum parasites (3D7 and Dd2 strains) in vitro. This work demonstrates...[Show more]

CollectionsANU Research Publications
Date published: 2019
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.9b01442


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