223386-36-5Relevant articles and documents
An effective Pd nanocatalyst in aqueous media: Stilbene synthesis by Mizoroki-Heck coupling reaction under microwave irradiation
García, Carolina S.,Uberman, Paula M.,Martín, Sandra E.
, p. 1717 - 1727 (2017/09/27)
Aqueous Mizoroki-Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h-1). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple product work-up make this protocol a great option for stilbene syntheses by Mizoroki-Heck reaction.
Design, synthesis, and evaluation of resveratrol derivatives as Ass1-42 aggregation inhibitors, antioxidants, and neuroprotective agents
Lu, Chuanjun,Guo, Yueyan,Li, Jianheng,Yao, Meicun,Liao, Qiongfeng,Xie, Zhiyong,Li, Xingshu
, p. 7683 - 7687 (2013/02/21)
A series of novel resveratrol derivatives were designed, synthesised and evaluated as potential therapeutic agents for the treatment of Alzheimer's disease. Among these compounds, compound 7l, (E)-5-(4-(isopropylamino)styryl) benzene-1,3-diol, exhibited potent ss-amyloid aggregation inhibition activity, which was confirmed by a ThT fluorescence assay (71.65% at 20 μM) and transmission electron microscopy (TEM). Compound 7l also exhibited good antioxidant activity (4.12 Trolox equivalents in an oxygen radical absorbance capacity assay and a 37% reduction in reactive oxygen species in cells at 10 μM). The cytotoxicity analysis of compounds 7f, 7i, 7j and 7l indicated that these compounds have lower toxicities than resveratrol at 60 μM.
Synthesis and anti-inflammatory activity of resveratrol analogs
Chen, Guoliang,Shan, Wei,Wu, Yingliang,Ren, Lixiang,Dong, Jinhua,Ji, Zhizhong
, p. 1587 - 1590 (2007/10/03)
Seventeen novel resveratrol derivatives were synthesized. Their anti-inflammatory activities were tested on xylene-induced mouse ear edema. The pharmacological results showed that some compounds have potent anti-inflammatory activities.
Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents
Botella, Luis,Nájera, Carmen
, p. 5563 - 5570 (2007/10/03)
The Heck reaction under phosphane free conditions using oxime-derived palladacycles or Pd(OAc)2 as catalysts is a general methodology for the synthesis of methoxylated (E)-stilbene derivatives. Couplings can be performed either with (dicyclohexyl)methylamine as base and TBAB in aqueous DMA or in neat water and with Et3N as base in DMA in air and under thermal and microwave conditions. The arylation of different styrenes are performed with 3,5-dimethoxyiodobenzene to afford a series of important biologically active (E)-stilbene derivatives containing the 3,5-dimethoxyphenyl moiety, including resveratrol, piceatannol and pinosilvine, which are efficiently prepared with high regioselectivity and total stereoselectivity (TON up to 104).
Styrylheterocycles as a novel class inhibitor of cyclooxygenase-2-mediated prostaglandin E2 production
Lee, Sang Kook,Park, Eun-Jung,Lee, Eunjung,Min, Hye-Young,Kim, Eun-Young,Lee, Taeho,Kim, Sanghee
, p. 2105 - 2108 (2007/10/03)
The inhibitory effects of a series of styrylheterocycles on the production of cyclooxygenase-2-mediated prostaglandin E2 (PGE2) were evaluated in lipopolysaccharide-stimulated RAW264.7 murine macrophages. A new series of potential inhibitors, including 3-[2-(4-methoxy-phenyl)-vinyl]- thiophene, have been identified, thus providing novel chemical leads for the further development of potential inhibitors in this capacity. The suppression of COX-2 mRNA expression by the active styrylheterocycles, in part, was involved in the inhibitory activity against the overproduction of PGE2.
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors
Kim,Ko,Jae Eun Park,Jung,Sang Kwang Lee,Chun
, p. 160 - 164 (2007/10/03)
A series of trans-stilbene derivatives containing a 3,5-dimethoxyphenyl moiety were prepared through a new efficient solution phase synthetic pathway, and their inhibitory activities were evaluated on human cytochrome P450s (CYP) 1A1, 1A2, and 1B1 to find a potent and selective CYP1B1 inhibitor. We found that a substituent at the 2-position of the stilbene skeleton plays a very important role in discriminating between CYP1As and CYP1B1. Among the compounds tested, the most selective and potent CYP1B1 inhibitor was 2,3',4,5'-tetramethoxystilbene. Compound 7j, 2-[2-(3,5-dimethoxy-phenyl)vinyl]thiophene, showed greater inhibitory activities but had a lower selectivity toward all of the CYPls tested.
Liquid-crystalline complexes of palladium(II) and platinum(II) with di- and tri-alkoxystilbazoles: Ligand control of mesomorphism
Donnio, Bertrand,Bruce, Duncan W.
, p. 2745 - 2755 (2007/10/03)
Liquid-crystalline complexes of palladium and platinum are formed when the metals are complexed to stilbazoles (4-styrylpyridines) bearing either two or three alkoxy chains. The complexes, termed polycatenar, show smectic C mesophases for most 3,4-disubstituted ligands, while the use of trisubstituted ligands leads to complexes showing columnar organisation, demonstrating that the spatial organisation of the metals in the liquid-crystal mesophase can be rather readily controlled. Complexes of these di- and tri-substituted stilbazoles with a cis-dicarbonylchloroiridium(I) fragment were not liquid crystalline.
