Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones

Guilherme A.M. Jardim, Thaissa L. Silva, Marilia O.F. Goulart, Carlos A. de Simone, Juliana M.C. Barbosa, Kelly Salomão, Solange L. de Castro, John F. Bower, Eufrânio N. da Silva Júnior

Research output: Contribution to journalArticle (Academic Journal)peer-review

22 Citations (Scopus)
326 Downloads (Pure)

Abstract

Thirty four halogen and selenium-containing quinones, synthesized by rhodium-catalyzed C-H bond activation and palladium-catalyzed cross-coupling reactions, were evaluated against bloodstream trypomastigotes of T. cruzi. We have identified fifteen compounds with IC50/24 h values of less than 2 μM. Electrochemical studies on A-ring functionalized naphthoquinones were also performed aiming to correlate redox properties with trypanocidal activity. For instance, (E)-5-styryl-1,4-naphthoquinone 59 and 5,8-diiodo-1,4-naphthoquinone 3, which are around fifty fold more active than the standard drug benznidazole, are potential derivatives for further investigation. These compounds represent powerful new agents useful in Chagas disease therapy.
Original languageEnglish
Pages (from-to)406–419
Number of pages14
JournalEuropean Journal of Medicinal Chemistry
Volume136
Early online date4 May 2017
DOIs
Publication statusPublished - 18 Aug 2017

Keywords

  • C-H functionalization
  • Quinones
  • Chagas disease
  • Trypanosoma cruzi
  • Electrochemistry

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