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Desymmetrization Reactions Of Indigo With Grignard Reagents For The Synthesis Of Selective Antiplasmodial [1 H,3′ H]-3-Aryl-2,2′-Diindol-3′-Ones, Nicholas Butler, John B. Bremner, Anthony C. Willis, Leonardo Lucantoni, Vicky M. Avery, Paul A. Keller
Desymmetrization Reactions Of Indigo With Grignard Reagents For The Synthesis Of Selective Antiplasmodial [1 H,3′ H]-3-Aryl-2,2′-Diindol-3′-Ones, Nicholas Butler, John B. Bremner, Anthony C. Willis, Leonardo Lucantoni, Vicky M. Avery, Paul A. Keller
Faculty of Science, Medicine and Health - Papers: Part B
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 the utility of indigo dye as a highly versatile scaffold for the synthesis of structurally diverse, bioactive heterocycles.
Investigation Of The Reactivity Of The Cytosine-5-Yl Radical Ion Using Ion Trap Mass Spectrometry, Tassiani Sarretto
Investigation Of The Reactivity Of The Cytosine-5-Yl Radical Ion Using Ion Trap Mass Spectrometry, Tassiani Sarretto
University of Wollongong Thesis Collection 2017+
Nucleobases play a significant biological role in DNA and RNA. Since the discovery that halogenated pyrimidines act as a good sensitizer for radiotherapy, the attention on 5-halouracil has increased, however the photoreactivity of cytosine and its derivatives has not been investigated. This study presents, for the first time, the highly selective generation of the cytosine-5-yl radical ion obtained by photodissociation of halogenated precursors. Using a modified linear ion trap mass spectrometer, gas-phase reactions and product channels are presented and mechanisms of possible pathways of photodissociation are discussed for reactions between the radical ion with molecular oxygen and unsaturated hydrocarbons including, …
Old Dye, New Tricks – Diversity-Oriented Synthesis Of Heterocycles From Cascade Reactions Of Indigo, Nicholas Matthew Butler
Old Dye, New Tricks – Diversity-Oriented Synthesis Of Heterocycles From Cascade Reactions Of Indigo, Nicholas Matthew Butler
University of Wollongong Thesis Collection 2017+
No abstract provided.