24144-92-1Relevant academic research and scientific papers
Antiproliferative activity of stilbene derivatives and other constituents from the stem bark of Morus nigra L
Abdel Bar, Fatma M.,Abbas, Ghada M.,Gohar, Ahmed A.,Lahloub, Mohamed-Farid I.
, p. 3506 - 3513 (2019/03/11)
The antiproliferative activities of 2′,3,4′,5,5′-pentahydroxy-cis-stilbene 1, resveratrol 2, oxyresveratrol 3, norartocarpetin 4, kuwanon C 5, morusin 6, cudraflavone A7, kuwanon G 8, albafuran C 9, mulberrofuran G 10, 3-acetyl-O-α-amyrin 11, 3-acetyl-O-β
AgSbF6-Catalyzed: Anti -Markovnikov hydroboration of terminal alkynes
Mamidala, Ramesh,Pandey, Vipin K.,Rit, Arnab
supporting information, p. 989 - 992 (2019/01/23)
AgSbF6-Catalyzed anti-Markovnikov addition of pinacolborane (HBpin) to terminal alkynes to produce the E-vinylboronates is reported. This efficient methodology is scalable, compatible with sterically and electronically diverse alkynes, and works at room temperature under solvent-free condition. The utility of this method is demonstrated in the facile synthesis of the clinically important (E)-2,4,3′,5′-tetramethoxystilbene.
Total synthesis of (±)-kuwanol e
Iovine, Valentina,Benni, Irene,Sabia, Rocchina,D'Acquarica, Ilaria,Fabrizi, Giancarlo,Botta, Bruno,Calcaterra, Andrea
, p. 2495 - 2503 (2016/11/09)
The total synthesis of the Diels-Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2′-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The syn
Oxyresveratrol synthesis method
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, (2016/10/17)
The invention provides an oxyresveratrol synthesis method which comprises the following steps: firstly performing a reflux reaction between raw materials 3,5-dimethoxybenzyl alcohol and phosphorus oxychloride; after the reaction is complete, pressurizing and recycling the solvent; filtering, washing to neutrality and drying to obtain 3,5-dimethoxybenzyl chloride; performing a reflux reaction between the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite in a solvent DMF (dimethyl formamide); after the reaction is complete, adding a catalyst sodium methylate solution, and adding a mixed solution of 2,4-dimethoxy benzaldehyde and DMF to obtain tetramethoxy diphenyl ethylene; and finally, performing a reflux reaction between the obtained tetramethoxy diphenyl ethylene and aluminum trichloride and xylene, wherein oxyresveratrol is obtained after the reaction is complete. According to the method provided by the invention, a Witting-Homer reaction is adopted, the raw materials are easily available, the yield is high, the cost is low, and the method is suitable for industrial production.
Oxyresveratrol: Structural modification and evaluation of biological activities
Chatsumpun, Nutputsorn,Chuanasa, Taksina,Sritularak, Boonchoo,Lipipun, Vimolmas,Jongbunprasert, Vichien,Ruchirawat, Somsak,Ploypradith, Poonsakdi,Likhitwitayawuid, Kittisak
, (2016/05/24)
Oxyresveratrol (2,4,3' ,5' -tetrahydroxystilbene, 1), a phytoalexin present in large amounts in the heartwood of Artocarpus lacucha Buch.-Ham., has been reported to possess a wide variety of biological activities. As part of our continuing studies on the structural modification of oxyresveratrol, a library of twenty-six compounds was prepared via O-alkylation, aromatic halogenation, and electrophilic aromatic substitution. The two aromatic rings of the stilbene system of 1 can be chemically modulated by exploiting different protecting groups. Such a strategy allows for selective and exclusive modifications on either ring A or ring B. All compounds were evaluated in vitro for a panel of biological activities, including free radical scavenging activity, DNA protective properties, antiherpetic activity, inhibition of α-glucosidase and neuraminidase, and cytotoxicity against some cancer cell lines. Several derivatives were comparably active or even more potent than the parent oxyresveratrol and/or the appropriate positive controls. The partially etherified analogs 5' -hydroxy-2,3' ,4-trimethoxystilbene and 3' ,5' -dihydroxy-2,4-dimethoxystilbene demonstrated promising anti-herpetic and DNA protective activities, offering new leads for neuropreventive agent research, whereas 5' -hydroxy-2,3' ,4,-triisopropoxystilbene displayed anti-α-glucosidase effects, providing a new lead molecule for anti-diabetic drug development. 3' ,5' -Diacetoxy-2,4-diisopropoxystilbene showed potent and selective cytotoxicity against HeLa cancer cells, but the compound still needs further in vivo investigation to verify its anticancer potential.
Comparative inhibitory activity of the stilbenes resveratrol and oxyresveratrol on African swine fever virus replication
Galindo,Hernaez,Berna,Fenoll,Cenis,Escribano,Alonso
, p. 57 - 63 (2012/05/04)
Stilbenols are polyphenolic phytoalexins produced by plants in response to biotic or abiotic stress. These compounds have received much attention because of their significant biological effects. One of these is their antiviral action, which has previously been documented for two members of this class, namely resveratrol and oxyresveratrol. Here we tested the antiviral effect of these two compounds on African swine fever virus, the only member of the newly created family Asfarviridae and a serious limitation to porcine production worldwide. Our results show a potent, dose-dependent antiviral effect of resveratrol and oxyresveratrol in vitro. Interestingly, this antiviral activity was found for these synthetic compounds and also for oxyresveratrol extracted from new natural sources (mulberry twigs). The antiviral effect of these two drugs was demonstrated at concentrations that do not induce cytotoxicity in cultured cells. Moreover, these antivirals achieved a 98-100% reduction in viral titers. Both compounds allowed early protein synthesis but inhibited viral DNA replication, late viral protein synthesis and viral factory formation.
Efficient synthesis of natural polyphenolic stilbenes: Resveratrol, piceatannol and oxyresveratrol
Sun, Hong-Yi,Xiao, Chun-Fen,Cai, Yu-Chen,Chen, Yu,Wei, Wen,Liu, Xian-Ke,Lv, Ze-Liang,Zou, Yong
experimental part, p. 1492 - 1496 (2010/12/25)
The practical synthesis of important natural polyphenolic stilbenes, including resveratrol, piceatannol and oxyresveratrol, through Perkin methodology is described. Starting from 3,5-dihydoxyacetophenone (1), the common intermediate 3,5-dimethoxyphenylacetic acid (3) can be obtained via methylation and Willgerodt-Kindler reaction. Perkin condensations between (3) and substituted phenylaldehydes 4 furnished E-2,3-diarylacrylic acids 5, followed by decarboxylation in Cu/quinoline giving stilbene intermediates 6 which bear the Z-configuration. Finally, through a simultaneous demethylation/isomerization process in AlI3/CH3CN system, the target compounds 7a-c can be obtained respectively in good to high overall yields. The synthetic method proved to be more concise, trans-specific, mild, economical and commonly applicable.
Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase
Song, Suhee,Lee, Hyojin,Jin, Youngeup,Ha, Young Mi,Bae, Sungjin,Chung, Hae Young,Suh, Hongsuk
, p. 461 - 464 (2007/10/03)
Oxyresveratrol and resveratrol, with hydroxy substituted trans-stilbene structure, exert potent inhibitory effects on cyclooxygenase, rat liver mitochondrial ATPase activity, and tyrosinase. As the isosteres of oxyresveratrol, a new family of hydroxyl sub
Synthesis of?stilbene derivatives with inhibition of?SARS coronavirus replication
Li, Yue-Qing,Li, Ze-Lin,Zhao, Wei-Jie,Wen, Rui-Xing,Meng, Qing-Wei,Zeng, Yi
, p. 1084 - 1089 (2007/10/03)
Stilbene derivatives have wide range of activities. In an effort to find other potential activities of this kind of compounds, 17 derivatives, including resveratrol, were synthesized. Twelve of them were evaluated for their antiviral potential against severe acute respiratory syndrome (SARS)-CoV-induced cytopathicity in Vero E6 cell culture. The result showed that SARS virus was totally inhibited by compounds 17 and 19 ( ≤ 0.5?mg?ml-1) and no significant cytotoxic effects were observed in vitro.
Chemical transformations of oxyresveratrol (trans-2,4,3′,5′-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent
Likhitwitayawuid, Kittisak,Sornsute, Acom,Sritularak, Boonchoo,Ploypradith, Poonsakdi
, p. 5650 - 5653 (2007/10/03)
From oxyresveratrol (trans-2,4,3′,5′-tetrahydroxystilbene 1), seven derivatives were prepared, including trans-2-methoxy-4,3′,5′-trihydroxystilbene (2), trans-2,3′-dimethoxy-4,5′-dihydroxystilbene (3), trans-4,3′-dimethoxy-2,5′-dihydroxystilbene (4), tran
