3860-01-3Relevant academic research and scientific papers
Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes
Deck, Lorraine M.,Whalen, Lisa J.,Hunsaker, Lucy A.,Royer, Robert E.,Vander Jagt, David L.
, p. 1423 - 1430 (2017/02/18)
Nrf2, which is a member of the cap'n’ collar family of transcription factors, is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. The importance of inflammation and oxidative stress in many chronic diseases supports the concept that activation of anti-oxidant Nrf2 signaling may have therapeutic potential. A number of Nrf2 activators have entered into clinical trials. Nrf2 exists in the cytosol in complex with its binding partner Keap1, which is a thiol-rich redox-sensing protein. In response to oxidative and electrophilic stress, select cysteine residues of Keap1 are modified, which locks Keap1 in the Nrf2-Keap1 complex and allows newly synthesized Nrf2 to enter the nucleus. Numerous Nrf2-activating chemicals, including a number of natural products, are electrophiles that modify Keap1, often by Michael addition, leading to activation of Nrf2. One concern with the design of Nrf2 activators that are electrophilic covalent modifiers of Keap1 is the issue of selectivity. In the present study, substituted trans stilbenes were identified as activators of Nrf2. These activators of Nrf2 are not highly electrophilic and therefore are unlikely to activate Nrf2 through covalent modification of Keap1. Dose-response studies demonstrated that a range of substituents on either ring of the trans stilbenes, especially fluorine and methoxy substituents, influenced not only the sensitivity to activation, reflected in EC50values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2. The stilbene backbone appears to be a privileged scaffold for development of a new class of Nrf2 activators.
β-cyclodextrin-capped palladium nanoparticle-catalyzed ligand-free Suzuki and Heck couplings in low-melting β-cyclodextrin/NMU mixtures
Zhao, Xiaohua,Liu, Xiang,Lu, Ming
, p. 635 - 640 (2014/08/05)
Low-melting β-cyclodextrin/N-methylurea (NMU) mixture, an efficient catalytic system for ligand-free Suzuki and Heck couplings in the presence of fresh native β-CD-capped Pd0 nanoparticles, has been successfully reported. This natural and convenient system can be performed in air and could afford the corresponding cross-coupled products in good to excellent isolated yields after a simple workup under every low Pd loading (0.05 mol%). Remarkably, the catalytic system can be recycled and reused without loss of catalytic activity. Copyright
Cross-coupling reactions catalyzed by an N-heterocyclic carbene-Pd(ii) complex under aerobic and CuI-free conditions
Lu, Hongfei,Wang, Lin,Yang, Feifei,Wu, Runze,Shen, Wei
, p. 30447 - 30452 (2014/08/05)
A Pd-complex, (Cat. 3), has been successfully employed as a highly efficient and recyclable catalyst for the Sonogashira and Heck reactions of aryl bromides with various terminal acetylenes and olefins. The catalytic reactions proceed with excellent yields with a low catalyst loading (1.0 mol%) under aerobic and CuI-free conditions. A plausible mechanism has also been proposed for the reaction. the Partner Organisations 2014.
Novel polymer supported iminopyridylphosphine palladium (∥) complexes: An efficient catalyst for Suzuki-Miyaura and Heck cross-coupling reactions
Liu, Xiang,Zhao, Xiaohua,Lu, Ming
, p. 23 - 27 (2014/07/21)
A novel cross-linked polyallylamine polymer supported iminopyridylphosphine palladium∥ complexes have been prepared and shown to be highly efficient catalysts for Suzuki-Miyaura and Heck cross-coupling reactions under low Pd loading (0.05% mol). Remarkably, the catalyst can be recycled and reused without loss of catalytic activity through simple filtration.
Design, synthesis and structure-activity relationships of some novel, highly potent anti-invasive (E)- and (Z)-stilbenes
Roman, Bart I.,De Coen, Laurens M.,Mortier, Séverine Thérèse F.C.,De Ryck, Tine,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc E.,Stevens, Christian V.
, p. 5054 - 5063 (2013/09/02)
In our ongoing exploration of the structure-activity landscape of anti-invasive chalcones, we have prepared and evaluated a number of structurally related (E)- and (Z)-stilbenes. These molecules exhibited an extraordinary high in vitro potency in the chick heart invasion assay, being active up to 10 nmol L-1, a concentration level a 100-fold lower than the lowest effective doses that have been reported for natural analogues. Furthermore, they possess an interesting pharmacological profile in silico.
Synthesis and biological evaluation of some stilbene-based analogues
Karki, Subhas S.,Bhutle, Santosh R.,Pedgaonkar, Ganesh S.,Zubaidha,Shaikh, Rizwan M.,Rajput, Chitra G.,Shendarkar, Girish S.
, p. 1158 - 1163 (2012/05/05)
The phytoalexin 3,5,40-trihydroxy-trans-stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. (E)-1-(3,4-difluorophenyl)-2-(4-fluorophenyl) ethene (4c) showed nearer equipotent antibacterial activity against Staphylococcus aureus. (E)-1,2-bis (4-fluorophenyl)ethene (4a), (E)-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene (4b), (E)-1-(2,4-dichlorophenyl)-2-(3, 4-dichlorophenyl)ethene (4f), (E)-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene (4g), (E)-1-(2,4- dichlorophenyl)-2-(4-fluorophenyl)ethene (4j) (E)-1-(4-fluorophenyl)-2-(3- chlorophenyl)ethene (4l) and (E)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene (4n) inhibited the growth of Penicillium chrysogenum. Springer Science+Business Media, LLC 2010.
