54808-21-8Relevant articles and documents
Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction
Borthakur, Somadrita,Baruah, Swagata,Sarma, Bipul,Gogoi, Sanjib
supporting information, p. 2768 - 2771 (2019/04/16)
An unprecedented Pd(II)-catalyzed decarbonylative C-H/C-C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.
Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones-green palladium-catalysed Suzuki cross coupling
Louvis, Aline Da R.,Silva, Nayane A. A.,Semaan, Felipe S.,Da Silva, Fernando De C.,Saramago, Gabriela,De Souza, Laís C. S. V.,Ferreira, Bruno L. A.,Castro, Helena C.,Salles, Juliana P.,Souza, André L. A.,Faria, Robson X.,Ferreira, Vitor F.,Martins, Daniela De L.
, p. 7643 - 7656 (2016/09/28)
Quinones are important scaffolds that are present in a variety of natural products or synthetic bioactive molecules. Arylation is an important strategy for accomplishing structural modifications, leading to new potential candidates for use as drugs. In the present work, palladium-catalysed, ligandless and phosphine-free Suzuki coupling reactions between 2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated. The Osiris and Molinspiration Cheminformatics programs, utilizing in silico analyses, imply that these naphthoquinones are candidates for use as drugs which was reinforced by the outcomes of the in vitro antifungal and trypanocidal activity tests. Our in vitro data indicated a MIC value of 8 μg mL-1 against Candida albicans ATCC 24433 strains, and an EC50 of 0.67 μM with respect to trypanocidal activity against Trypanosoma cruzi epimastigote strains (Y).
1,4-naphthoquinone cations as antiplasmodial agents: Hydroxy-, acyloxy-, and alkoxy-substituted analogues
Lu, Xiao,Altharawi, Ali,Gut, Jiri,Rosenthal, Philip J.,Long, Timothy E.
supporting information, p. 1029 - 1033 (2013/02/22)
Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4-49.5 nM against heteroresistant P. falciparum W2.
