18513-95-6Relevant academic research and scientific papers
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.
Anticancer Evaluation of 3,4,5,4'-trans-tetramethoxystilbene (DMU-212) and Its Analogs Against an Extensive Panel of Human Tumor Cell Lines
Madadi, Nikhil Reddy,Crooks, Peter Anthony
, p. 521 - 528 (2016/03/22)
DMU-212, a methoxylated resveratrol analog, has significant anticancer activity, and selectively targets tumor cells. A library of E-diarylstilbenes structurally related to DMU-212 has been synthesized and evaluated for anticancer activity against a large
Mechanically activated synthesis of (E)-stilbene derivatives by high-speed ball milling
Zhu, Xingyi,Liu, Jun,Chen, Tao,Su, Weike
experimental part, p. 145 - 147 (2012/05/05)
An efficient mechanically activated solvent-free synthesis of (E)-stilbene derivatives by high-speed ball milling is described. This method has notable advantages in terms of good yield, short reaction time and high selectivity. Copyright
Microwave-assisted, aqueous wittig reactions: Organic-solvent- And protecting-group-free chemoselective synthesis of functionalized alkenes
McNulty, James,Das, Priyabrata,McLeod, David
supporting information; experimental part, p. 6756 - 6760 (2010/08/06)
(Chemical Equation Presented) Free from protection! A general, chemoselective, protecting-group- and organic-solvent-free route to stilbenes and heterostilbenes involving the direct synthesis of triethyl benzylic and allylic phosphonium salts from the corresponding alcohols and their microwave-assisted, aqueous Wittig reactions is described.
Wittig-type olefination of alcohols promoted by nickel nanoparticles: Synthesis of polymethoxylated and polyhydroxylated stilbenes
Alonso, Francisco,Riente, Paola,Yus, Miguel
supporting information; experimental part, p. 6034 - 6042 (2010/02/28)
Nickel nanoparticles were found to promote the Wittig-type olefination of primary alcohols with phosphorus ylides. The latter can be prepared from the corresponding phosphonium salts with TiBuLi or in situ generated with lithium metal. The methodology is especially efficient for the synthesis of stilbenes and is applied in the absence of any additive as a hydrogen acceptor. A new approach, to the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol, DMU-212 and analogues, is presented.
Synthesis and biological evaluation of some enantiomerically pure C8cC15 monoseco analogues of the phenanthroquinolizidine-type alkaloids cryptopleurine and julandine
Sydnes, Magne O.,Bezos, Anna,Burns, Christopher,Kruszelnicki, Irma,Parish, Christopher R.,Su, Stephen,Rae, A. David,Willis, Anthony C.,Banwell, Martin G.
, p. 506 - 520 (2008/12/20)
A series of enantiomerically pure C8cC15 monoseco analogues, 2330, of the alkaloids cryptopleurine (1) and julandine (2) have been prepared using cinnamyl chloride 37 and (S)- or (R)-2-methylpiperidine as key building blocks. Two related compounds, 31 and
Heck arylation of styrenes with arenediazonium salts: short, efficient, and stereoselective synthesis of resveratrol, DMU-212, and analogues
Moro, Angélica Venturini,Cardoso, Flávio Sega P.,Correia, Carlos Roque D.
, p. 5668 - 5671 (2008/12/22)
Short, efficient, and stereoselective synthesis of the trans-stilbenes resveratrol, DMU-212, and analogues of both compounds are described. The synthesis of these important anti-cancer agents feature the palladium catalyzed Heck-Matsuda arylation of styre
Quinone reductase induction activity of methoxylated analogues of resveratrol
Zhang,Go
, p. 841 - 850 (2008/02/12)
Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase II enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-methoxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents.
Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes
Lebel, Helene,Ladjel, Chehla,Brethous, Lise
, p. 13321 - 13326 (2008/09/17)
Palladium-catalyzed cross-coupling reactions have been investigated in multicatalytic processes to synthesize disubstituted alkenes and alkanes from carbonyl derivatives. The use of copper-catalyzed methylenation reactions is the key starting reaction to produce terminal alkenes which are not isolated, but submitted to further structure elongation. Not only is the isolation of the alkene intermediate unnecessary, but also the copper catalyst is a beneficial cocatalyst in the palladium-catalyzed cross-coupling reactions. The desired products are thus typically obtained in higher yields using this one-pot approach. We have used these processes to synthesize hydroxylated (E)-stilbenoids, which are known chemopreventive and chemotherapeutic agents, odorant-substituted indanes, and non-natural amino acids, such as homophenylalanine.
An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction
Sinha, Arun K.,Kumar, Vinod,Sharma, Abhishek,Sharma, Anuj,Kumar, Rakesh
, p. 11070 - 11077 (2008/02/12)
A mild and convenient one-pot two-step synthesis of hydroxystilbenes with trans selectivity has been developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence of piperidine-methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation-decarboxylation leading to the unusual formation of hydroxystilbenes in lieu of α-phenylcinnamic acid reveals an interesting facet to the classical Perkin reaction. The developed protocol provides a green alternative to the prevalent methods employing a toxic decarboxylating agent in the form of quinoline/Cu salt, and the requirement for harsh protection-deprotection steps for the synthesis of hydroxylated stilbenes.
