33522-29-1Relevant articles and documents
Overcoming naphthoquinone deactivation: Rhodium-catalyzed C-5 selective C-H iodination as a gateway to functionalized derivatives
Jardim, Guilherme A. M.,Da Silva, Eufranio N.,Bower, John F.
, p. 3780 - 3784 (2016)
We report a Rh-catalyzed method for the C-5 selective C-H iodination of naphthoquinones and show that complementary C-2 selective processes can be achieved under related conditions. C-C bond forming derivatizations of the C-5 iodinated products provide a gateway to previously inaccessible A-ring analogues. The present study encompasses the first catalytic directed ortho-functionalizations of simple (non-bias) naphthoquinones. The strategic considerations outlined here are likely to be applicable to C-H functionalizations of other weakly coordinating and/or redox sensitive substrates.
Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones
Jardim, Guilherme A.M.,Silva, Thaissa L.,Goulart, Marilia O.F.,de Simone, Carlos A.,Barbosa, Juliana M.C.,Salom?o, Kelly,de Castro, Solange L.,Bower, John F.,da Silva Júnior, Eufranio N.
, p. 406 - 419 (2017/05/19)
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.
