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

European Journal of Medicinal Chemistry
Guilherme A M JardimEufrânio N da Silva Júnior

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.

Citations

Jan 6, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guilherme A M JardimEduardo H G da Cruz
Jun 5, 2018·Chemical Communications : Chem Comm·Eufrânio N da Silva JúniorLutz Ackermann
Oct 31, 2018·Chemical Communications : Chem Comm·Gleiston G DiasLutz Ackermann
Nov 12, 2019·Archiv der Pharmazie·Christian Espinosa-BustosCristian O Salas
Jan 9, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·James M WoodEufrânio N da Silva Júnior
Apr 20, 2021·ACS Infectious Diseases·Rubén Martín-EscolanoClotilde Marín
Jul 4, 2021·European Journal of Medicinal Chemistry·Hongyan ChuaiMinhang Xin

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