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.
Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological activity and molecular modelling evidence for cooperativity between viniferin enantiomers
Mattio, Luce M.,Marengo, Mauro,Parravicini, Chiara,Eberini, Ivano,Dallavalle, Sabrina,Bonomi, Francesco,Iametti, Stefania,Pinto, Andrea
, (2019/09/09)
To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.
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.
Preparation method of resveratrol compound
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Paragraph 0064; 0065, (2019/07/16)
The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.
Synthesis method of piceatannol
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, (2018/11/03)
The invention provides piceatannol. A target product piceatannol is prepared through the steps of taking 3-hydroxyl-4-methoxybenzaldehyde as a starting raw material, carrying out wittig reaction to generate 3-hydroxyl-4-methoxystyrene, carrying out Heck r
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.
Method for synthesizing artificially all-trans-resveratrol and derivative thereof
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Paragraph 0036; 0037, (2017/08/31)
The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.
A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)
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Paragraph 0079-0080, (2017/08/27)
The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)
Synthetic method for piceatannol derivatives and pharmaceutical compounds containing the piceatannol derivatives
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Paragraph 0023; 0034; 0035, (2017/10/31)
The piceatannol derivatives were easily synthesized using a Wittig-Horner reaction, a Colvin rearrangement and a Sonogashira reaction. According to the result of investigating the anti-inflammatory activity of compounds synthesized in RAW264.7 macrophages induced by LPS, compounds 6 to 8 showed remarkable activity at the concentration of 10 andmu;M, and a compound 7 (90.1%), a compound 8 (60.8%) and a compound 6 (55.2%) showed no cytotoxicity. The present invention aims to provide a method for efficiently synthesizing the piceatannol derivatives and to confirm the biological activity of synthesized piceatannol derivatives.COPYRIGHT KIPO 2017
A focused multiple reaction monitoring (MRM) quantitative method for bioactive grapevine stilbenes by ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ)
Hurtado-Gaitán, Elías,Sellés-Marchart, Susana,Martínez-Márquez, Ascensión,Samper-Herrero, Antonio,Bru-Martínez, Roque
, (2017/03/23)
Grapevine stilbenes are a family of polyphenols which derive from trans-resveratrol having antifungal and antimicrobial properties, thus being considered as phytoalexins. In addition to their diverse bioactive properties in animal models, they highlight a strong potential in human health maintenance and promotion. Due to this relevance, highly-specific qualitative and quantitative methods of analysis are necessary to accurately analyze stilbenes in different matrices derived from grapevine. Here, we developed a rapid, sensitive, and specific analysis method using ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ) in MRM mode to detect and quantify five grapevine stilbenes, trans-resveratrol, trans-piceid, trans-piceatannol, trans-pterostilbene, and trans-?-viniferin, whose interest in relation to human health is continuously growing. The method was optimized to minimize in-source fragmentation of piceid and to avoid co-elution of cis-piceid and trans-resveratrol, as both are detected with resveratrol transitions. The applicability of the developed method of stilbene analysis was tested successfully in different complex matrices including cellular extracts of Vitis vinifera cell cultures, reaction media of biotransformation assays, and red wine.
