1218-24-2Relevant articles and documents
Rhodium(III)-catalyzed dehydrogenative Heck reaction of salicylaldehydes
Shi, Zhuangzhi,Schr?der, Nils,Glorius, Frank
, p. 8092 - 8096 (2012)
Your CHOice! An efficient RhIII-catalyzed dehydrogenative Heck reaction (DHR) of salicylaldehydes with different classes of olefins extends the oxidative Heck reaction to aldehyde C-H bonds. Several structural motifs similar to natural products and bioactive molecules such as aurones, flavones, 2'-hydroxychalcones, and flavanones could be efficiently produced. Initial mechanistic studies give insight into the reaction mechanism. Copyright
Enzyme-assisted cyclization of chalcones to flavanones
Alonso, Mariana Macías,Boluda, Carlos José,Barajas, Gabriela Díaz,Sánchez, Nallely Caldera,Córdova-Guerrero, Iván,Marrero, Joaquín González
, p. 926 - 931 (2020/12/23)
Enzyme catalyzed synthesis is an eco-friendly technique in organic synthesis, having several benefits over conventional methods. In the present work, we describe a simple process of laccase and chloroperoxidase assisted cyclization of chalcones, leading to the formation of flavanones. The reaction proceeds in a mixture of phosphate buffer and ethanol, under oxygen atmosphere at room temperature, yielding the corresponding flavanone in good to moderate yield. The relative configuration of the products at C2 is tentatively assigned as S*-flavanone based on the coupling constants with the methylenic protons H3α,β. In comparison to the chemical methods, we describe a process which can be achieved efficiently under mild conditions using oxygen as oxidant.
Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi
Coelho, Gleicekelly Silva,Andrade, Josimara Souza,Xavier, Viviane Flores,Sales Junior, Policarpo Ademar,Rodrigues de Araujo, Barbara Caroline,Fonseca, Kátia da Silva,Caetano, Melissa Soares,Murta, Silvane Maria Fonseca,Vieira, Paula Melo,Carneiro, Claudia Martins,Taylor, Jason Guy
, p. 337 - 350 (2018/12/05)
Chagas disease is caused by infection with the parasite protozoan Trypanosoma cruzi and affects about 8 million people in 21 countries in Latin America. The main form of treatment of this disease is still based on the use of two drugs, benznidazole and nifurtimox, which both present low cure rates in the chronic phase and often have serious side-effects. Herein, we describe the synthesis of tricyclic coumarins that were obtained via NHC organocatalysis and evaluation of their trypanocidal activity. Molecular docking studies against trypanosomal enzyme triosephosphate isomerase (TIM) were carried out, as well as a theoretical study of the physicochemical parameters. The tricyclic coumarins were tested in vitro against the intracellular forms of Trypanosoma cruzi. Among the 18 compounds tested, 10 were more active than the reference drug benznidazole. The trypanocidal activity of the lead compound was rationalized by molecular docking study which suggested the strong interaction with the enzyme TIM by T.?cruzi and therefore indicating a possible mode of action. Furthermore, the selectivity index of eight tricyclic coumarins with high anti-T.?cruzi activity was above 50 and thus showing that these lead compounds are viable candidates for further in vivo assays.
