1222993-28-3Relevant academic research and scientific papers
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.
Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation
Jardim, Guilherme A. M.,Bower, John F.,Da Silva Júnior, Eufranio N.
supporting information, p. 4454 - 4457 (2016/09/28)
Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.
Quinone dimers connected by 1,4-phenylene and 2,5-thienylene moieties as a π-linker
Hayashi, Naoto,Sakakibara, Teru,Ohnuma, Takahiro,Yoshino, Junro,Higuchi, Hiroyuki
experimental part, p. 1227 - 1238 (2010/10/01)
The synthesis and characterization of quinone dimers connected by 1,4-phenylene (QPQ) and 2,5-thienylene (QTQ) linkers are described. QPQ and QTQ were synthesized by means of Suzuki coupling and subsequent oxidation. Significant bathochromic shifts were observed in the electronic absorption spectra of QPQ and QTQ as compared to that of the quinine dimers without a linker. In addition, cyclic voltammetry and DFT calculations demonstrated that QTQ was a stronger electron acceptor than QPQ due to its planar structure, even though QTQ contains an electron-rich thiophene ring.
