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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

Journal Article


Abstract


  • 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.

UOW Authors


  •   Butler, Nicholas (external author)
  •   Bremner, John
  •   Willis, Anthony C. (external author)
  •   Lucantoni, Leonardo (external author)
  •   Avery, Vicky M. (external author)
  •   Keller, Paul

Publication Date


  • 2019

Citation


  • Butler, N. M., Bremner, J. B., Willis, A. C., Lucantoni, L., Avery, V. M. & Keller, P. A. (2019). Desymmetrization Reactions of Indigo with Grignard Reagents for the Synthesis of Selective Antiplasmodial [1 H,3′ H]-3-Aryl-2,2′-diindol-3′-ones. Journal of Organic Chemistry, 84 11228-11239.

Scopus Eid


  • 2-s2.0-85071655533

Number Of Pages


  • 11

Start Page


  • 11228

End Page


  • 11239

Volume


  • 84

Place Of Publication


  • United States

Abstract


  • 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.

UOW Authors


  •   Butler, Nicholas (external author)
  •   Bremner, John
  •   Willis, Anthony C. (external author)
  •   Lucantoni, Leonardo (external author)
  •   Avery, Vicky M. (external author)
  •   Keller, Paul

Publication Date


  • 2019

Citation


  • Butler, N. M., Bremner, J. B., Willis, A. C., Lucantoni, L., Avery, V. M. & Keller, P. A. (2019). Desymmetrization Reactions of Indigo with Grignard Reagents for the Synthesis of Selective Antiplasmodial [1 H,3′ H]-3-Aryl-2,2′-diindol-3′-ones. Journal of Organic Chemistry, 84 11228-11239.

Scopus Eid


  • 2-s2.0-85071655533

Number Of Pages


  • 11

Start Page


  • 11228

End Page


  • 11239

Volume


  • 84

Place Of Publication


  • United States