38987-00-7Relevant articles and documents
Total Synthesis of Xanthoangelol B and Its Various Fragments: Toward Inhibition of Virulence Factor Production of Staphylococcus aureus
Mizar, Pushpak,Arya, Rekha,Kim, Truc,Cha, Soyoung,Ryu, Kyoung-Seok,Yeo, Won-Sik,Bae, Taeok,Kim, Dae Wook,Park, Ki Hun,Kim, Kyeong Kyu,Lee, Seung Seo
, p. 10473 - 10487 (2018/11/23)
As an alternative strategy to fight antibiotic resistance, two-component systems (TCSs) have emerged as novel targets. Among TCSs, master virulence regulators that control the expression of multiple virulence factors are considered as excellent antivirulence targets. In Staphylococcus aureus, virulence factor expression is tightly regulated by a few master regulators, including the SaeRS TCS. In this study, we used a SaeRS GFP-reporter system to screen natural compound inhibitors of SaeRS, and identified xanthoangelol B 1, a prenylated chalcone from Angelica keiskei as a hit. We have synthesized 1 and its derivative PM-56 and shown that 1 and PM-56 both had excellent inhibitory potency against the SaeRS TCS, as demonstrated by various in vitro and in vivo experiments. As a mode of action, 1 and PM-56 were shown to bind directly to SaeS and inhibit its histidine kinase activity, which suggests a possibility of a broad spectrum inhibitor of histidine kinases.
Regioselectivity in aromatic Claisen rearrangements
Gozzo, Fabio Cesar,Fernandes, Sergio Antonio,Rodrigues, Denise Cristina,Eberlin, Marcos Nogueira,Marsaioli, Anita Jocelyne
, p. 5493 - 5499 (2007/10/03)
Theoretical calculations and the isomeric product composition for a series of eight meta-substituted allyl aryl ethers confirm the reliability of a new 1H NMR methodology used to predict aromatic Claisen regioselectivity from ground-state confo
Synthesis of the leukotriene antagonist ablukast
Manchand,Micheli,Saposnik
, p. 9391 - 9398 (2007/10/02)
An efficient synthesis of the leukotriene antagonist ablukast (5) has been achieved starting from 2,4-dihydroxyacetophenone. The latter, on a Claisen condensation with ethyl oxalate, followed by hydrogenation, gave the chromane ester 7, which was subjected to a Fries rearrangement (AcOH/BF3·OEt2) and the product, after transesterification with methanol, was alkylated with 5-bromo-1-pentanyl acetate to afford the acetate 9. A novel methanolysis of 9 with methanol in the presence of tetra-n-butylammonium hydroxide followed by mesylation of the derived alcohol furnished the mesylate 10. Alkylation of the acetophenone derivative 16 with 10 using K2CO3 in the presence of tris(3,6-dioxaheptyl)amine and saponification gave 5.
