39032-14-9Relevant academic research and scientific papers
Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols
Nagasawa, Shota,Fujiki, Shogo,Sasano, Yusuke,Iwabuchi, Yoshiharu
, p. 6952 - 6968 (2021/05/29)
We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.
In vitro study and structure-activity relationship analysis of stilbenoid derivatives as powerful vasorelaxants: Discovery of new lead compound
Chan, Sock Ying,Loh, Yean Chun,Oo, Chuan Wei,Yam, Mun Fei
, (2020/10/12)
The development of vasorelaxant as the antihypertensive drug is important as it produces a rapid and direct relaxation effect on the blood vessel muscles. Resveratrol (RV), as the most widely studied stilbenoid and the lead compound, inducing the excellent vasorelaxation effect through the multiple signalling pathways. In this study, the in vitro vascular response of the synthesized trans-stilbenoid derivatives, SB 1-8e were primarily evaluated by employing the phenylephrine (PE)-precontracted endothelium-intact isolated aortic rings. Herein we report trans-3,4,4′-trihydroxystilbene (SB 8b) exhibited surprisingly more than 2-fold improvement to the maximal relaxation (Rmax) of RV. This article also highlights the characterization of the aromatic protons in terms of their unique splitting patterns in 1H NMR.
Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction
Srivastava, Vivek
, p. 693 - 703 (2017/03/08)
Abstract: Five different Ru metal precursors were reduced in imidazolium based ionic liquids under hydrogen atmosphere (4?bar) at 50 °C to obtain well-dispersed and stable Ru nanoparticles. Transmission electron microscopy (TEM) analysis confirmed size of well dispersed ionic liquid mediated Ru particles (Ru NPs) of 5?nm (±0.5) in diameter. These ruthenium nanoparticles (in ionic liquids) were used for Wittig type olefination reaction under mild reaction environment (70 °C and 1?h). The corresponding stilbenes were obtained in good yield with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212. Graphical Abstract: [Figure not available: see fulltext.]
Olefination of N-Sulfinylimines under Mild Conditions
Dhara, Shubhendu,Diesendruck, Charles E.
, p. 1184 - 1190 (2017/03/11)
A very simple and efficient diastereoselective synthesis of 1,2-disubstituted alkenes has been achieved under mild conditions. Sulfoxide stabilised N-sulfinylimines reacted with in-situ-generated phosphonate carbanions to give 1,2-disubtituted alkenes in good to excellent yields. Different aryl phosphonates reacted with a range of electronically diverse N-sulfinylimines to give alkenes with >99:1 E selectivity. The most important feature of this protocol is that the reaction can be carried out at room temperature with inexpensive sodium hydride as the most effective base to generate the reactive phosphonate carbanions, and producing the alkenes with E selectivity in up to 85 % isolated yield.
TRPA1 channels as targets for resveratrol and related stilbenoids
Nalli, Marianna,Ortar, Giorgio,Moriello, Aniello Schiano,Morera, Enrico,Di Marzo, Vincenzo,De Petrocellis, Luciano
, p. 899 - 902 (2016/05/24)
A series of twenty resveratrol analogues was synthesized and tested on TRPA1 and TRPV1 channels. None was able to significantly modulate TRPV1 channels. Conversely, most of them exhibited remarkably higher TRPA1 modulating activity than resveratrol. Optimal potency was observed with ortho monoxygenated stilbenes 6 and 17.
Stereoselective peterson olefinations from bench-stable reagents and N-phenyl imines
Das, Manas,Manvar, Atul,Jacolot, Ma?wenn,Blangetti, Marco,Jones, Roderick C.,O'Shea, Donal F.
, p. 8737 - 8740 (2015/06/08)
The synthesis of bench-stable α,α-bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ～1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N-benzylideneaniline (up to 99:1) as an alternative electrophile. The olefination byproduct was identified as N,N-bis(trimethylsilyl)aniline and could be easily separated from product by aqueous acid extraction. Evidence for an autocatalytic cycle has been obtained.
THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS
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Page/Page column 36; 48-49; 54, (2015/06/18)
The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.
Visible light-mediated oxidative quenching reaction to electron-rich epoxides: Highly regioselective synthesis of α-bromo (di)ketones and mechanism study
Guo, Lin,Yang, Chao,Zheng, Lewei,Xia, Wujiong
supporting information, p. 5787 - 5792 (2013/09/12)
A novel and simple procedure was developed for the regioselective synthesis of α-bromo (di)ketones from electron-rich epoxides via visible light photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved under mild conditions. Moreover, the possible reaction mechanism was proposed and further supported by control experiments.
Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
, p. 3674 - 3691 (2013/06/27)
4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
Feeding the Heck reaction with alcohol: One-pot synthesis of stilbenes from aryl alcohols and bromides
Colbon, Paul,Barnard, Jonathan H.,Purdie, Mark,Mulholland, Keith,Kozhevnikov, Ivan,Xiao, Jianliang
, p. 1395 - 1400 (2012/07/03)
Aryl alcohols are employed as feedstock for the Heck reaction. Keggin-type heteropolyacids catalyse the selective dehydration of the alcohols to styrenes, which, in one-pot, undergo palladium-catalysed Heck arylation with aryl bromides, affording broadly functionalised stilbenes. The choice of solvent is critical for the cascade dehydration-Heck reaction, with electron-rich aryl alcohols preferring a basic medium while electron-deficient ones demanding solvents of lower basicity. Copyright
