22255-22-7Relevant articles and documents
Complete assignment of the1H and13C NMR spectra of resveratrol derivatives
Koh, Dongsoo,Park, Kwan Ha,Jung, Jihyun,Yang, Heejung,Hun Mok,Lim, Yoongho
, p. 768 - 770 (2001)
Contract/grant sponsor: Korea Ministry of Marine Affairs and Fishery The complete 1H and 13C chemical shift assignments of six derivatives of resveratrol [(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol] that possess leukotriene D
Heterogeneous heck coupling in multivariate metal-organic frameworks for enhanced selectivity
Brown, Jonathan W.,Jarenwattananon, Nanette N.,Otto, Trenton,Wang, James L.,Gl?ggler, Stefan,Bouchard, Louis-S.
, p. 105 - 107 (2015)
Abstract Highly selective heterogeneous Heck coupling has been demonstrated inside a series of metal-organic frameworks (MOFs). These MOFs, Zn4O(BDC-NH2)n(BDC)(3 - n) (n = 3, 2.4, 1.8, 1.2, 0.9, 0.75, 0.6, 0.3,
Novel resveratrol-based flavonol derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo
Chen, Liu Zeng,Yao, Li,Jiao, Ming Ming,Shi, Jing Bo,Tan, Yue,Ruan, Ban Feng,Liu, Xin Hua
, p. 114 - 128 (2019)
In order to discover novel anti-inflammatory agents, total thirty-seven new resveratrol-based flavonol derivatives were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition effect of LPS-induced NO production in RAW 264.7 macrophages. Their toxicity was also assessed in vitro. Structure-activity relationships (SARs)have been concluded, and finally 2-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)-3-hydroxy-4H-chromen-4-one was found to be the most active scaffold with low toxicity. This compound could significantly decrease productions of NO, IL-6 and TNF-α with IC50 values of 1.35, 1.12 and 1.92 μM, respectively in RAW 264.7 macrophages. Preliminary mechanism studies indicated that it could inhibit the expression of TLR4 protein, resulting in activation of the NF-?B cell signaling pathway. The in vivo anti-inflammatory activity of this compound could reduce pulmonary inflammation by mouse model of LPS-induced acute lung injury (ALI). We believe these findings would further support studies of rational design of more efficient acute lung injury regulatory inhibitors.
Jiewei, Tian,Lei, Wang,Xiufeng, Long,Heming, Zhang,Xiaoguang, Li,Haiyan, Fu,Yongqiang, Tian
, p. 2343 - 2346 (2018)
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Ingham,J.L.
, p. 1791 - 1793 (1976)
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An expedient synthesis of resveratrol through a highly recoverable palladium catalyst
Martínez, Alejandro V.,García, José I.,Mayoral, José A.
, p. 5581 - 5584 (2017)
A straightforward two-step synthesis of resveratrol is described, with total isolated yields in the range of 75–80%. The key synthetic step, a Heck–Mizoroki C[sbnd]C cross-coupling reaction, is efficiently promoted by a heterogeneous catalyst consisting of palladium nanoparticles supported on synthetic clay. This solid catalyst is quite handy and displays high stability and robustness under reaction conditions. The catalyst can be easily recovered and reused at least 10 times, which improves the overall catalytic efficiency of the system. Moreover, the use of solvents is limited, and the reaction procedure allows a facile separation and purification of the desired product, free from the concomitant ionic by-product and from palladium contamination.
Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis
Babu, Reshma,Balaraman, Ekambaram,Midya, Siba P.,Subaramanian, Murugan,Yadav, Vinita
, p. 7552 - 7562 (2021/06/28)
The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.
Non-Chelate-Assisted Palladium-Catalyzed Aerobic Oxidative Heck Reaction of Fluorobenzenes and Other Arenes: When Does the C?H Activation Need Help?
Albéniz, Ana C.,Villalba, Francisco
supporting information, p. 4795 - 4804 (2021/09/06)
The pyridone fragment in the ligand [2, 2’-bipyridin]-6(1H)-one (bipy-6-OH) enables the oxidative Heck reaction of simple arenes with oxygen as the sole oxidant and no redox mediator. Arenes with either electron-donating or electron-withdrawing groups can be functionalized in this way. Experimental data on the reaction with toluene as the model arene shows that the C?H activation step is turnover limiting and that the ligand structure is crucial to facilitate the reaction, which supports the involvement of the pyridone fragment in the C?H activation step. In the case of fluoroarenes, the alkenylation of mono and 1,2-difluoro benzenes requires the presence of bipy-6-OH. In contrast, this ligand is detrimental for the alkenylation of 1,3-difluoro, tri, tetra and pentafluoro benzenes which can be carried out using just [Pd(OAc)2]. This correlates with the acidity of the fluoroarenes, the most acidic undergoing easier C?H activation so other steps of the reaction such as the coordination-insertion of the olefin become kinetically important for polyfluorinated arenes. The use of just a catalytic amount of sodium molybdate as a base proved to be optimal in all these reactions. (Figure presented.).
Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
Birar, Vishal C.,Faragher, Richard G. A.,Ostler, Elizabeth L.,Sheerin, Angela N.
, p. 817 - 826 (2020/08/17)
Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25–50 μM typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 μM enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated β galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 μM many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 μM, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
