106325-86-4Relevant articles and documents
Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C-O Bond Cleavage
Qiu, Xiaodong,Li, Yangyang,Zhou, Li,Chen, Peishan,Li, Fan,Zhang, Yanan,Ling, Yong
supporting information, p. 6424 - 6428 (2020/08/24)
A new protocol has been developed for the borylation of conjugated alkenyl methyl ethers using B2Pin2 via C-O bond cleavage catalyzed by Ni(II). In this cross-coupling reaction, both E/Z isomers of alkenyl ethers are converted into (E)-alkenyl boronic esters with good reactivity. This transformation exhibits high chemoselectivity in the presence of competitive C-O bonds such as aryl ether, ester, amide, and thioether groups, thus providing a new method for the construction of various alkenyl boronates.
Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors
Boccellino, Mariarosaria,Donniacuo, Maria,Bruno, Ferdinando,Rinaldi, Barbara,Quagliuolo, Lucio,Ambruosi, Marika,Pace, Simona,De Rosa, Mario,Olga?, Abdurrahman,Banoglu, Erden,Alessio, Nicola,Massa, Antonio,Kahn, Haroon,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna
, p. 637 - 647 (2019/07/31)
Stilbenes with well-known antioxidant and antiradical properties are beneficial in different pathologies including cardiovascular diseases. The present research was performed to investigate the potential protective effect of resveratrol (1) and piceatannol (2), against hypoxia-induced oxidative stress in the H9c2 cardiomyoblast cell line, and the underlying mechanisms. Compounds 1 and 2 significantly inhibited the release of peroxynitrite and thiobarbituric acid levels at na no- or submicromolar concentrations, and this effect was more evident in piceatannol-treated cells, that significantly increased MnSOD protein level in a concentration dependent manner. Furthermore, since piceatannol, which is far less abundant in natural sources, displayed a higher bioactivity than the parent compound, we hereby report on a very fast synthesis and detailed structure-based design of a focused stilbene library. Finally, taking into account that hypoxia-induced ROS accumulation also increases expression and activity of 5-lipoxygenase (5-LOX) with production of leukotrienes, we have disclosed structural key factors crucial for 5-LOX activity. Among the synthesized analogues (3–7), compound 7 was the most effective in improving cardiomyocytes viability and in 5-LOX inhibition. In conclusion, modeling and experimental studies provided the basis for further optimization of stilbene analogues as multi-target inhibitors of the inflammatory and oxidative pathway.
Enzymatic synthesis of catechol-functionalized polyphenols with excellent selectivity and productivity
Cheng, Hui,Zou, Yong,Luo, Xiang,Song, Xian-Heng,Yang, Zhen
, p. 90 - 97 (2018/04/11)
Polyphenol products have become more and more attractive due to their strong anti-oxidant properties and a great variety of promising pharmacological activities and beneficial effects on human health. In this study, mushroom tyrosinase immobilized as cross-linked enzyme aggregates (CLEAs) was used as the catalyst for ortho-hydroxylation reactions to produce 3,4-dihydroxyphenylacetic acid, piceatannol and 3′-hydroxypterostilbene from 4-hydroxyphenylacetic acid, resveratrol and pterostilbene, respectively, with excellent selectivity and productivity. This is the first report of synthesizing these three polyphenolic compounds with tyrosinase CLEAs as catalyst, and the first study of biocatalytic production of 3′-hydroxypterostilbene. Introducing a deep eutectic solvent (DES) into the tyrosinase CLEA preparation exhibited a positive effect in terms of enhancing the catalytic activity of the immobilized enzyme and also promoting the synthesis of the polyphenol products.
