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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 language | English |
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Pages (from-to) | 406–419 |
Number of pages | 14 |
Journal | European Journal of Medicinal Chemistry |
Volume | 136 |
Early online date | 4 May 2017 |
DOIs | |
Publication status | Published - 18 Aug 2017 |
Keywords
- C-H functionalization
- Quinones
- Chagas disease
- Trypanosoma cruzi
- Electrochemistry
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Dive into the research topics of 'Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones'. Together they form a unique fingerprint.Projects
- 1 Finished
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research