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(Z)-(2-bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis
Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of a wide range of functional small molecules. In this context, (Z)-(2-bromovinyl)-N-methyliminodiacetic acid (MIDA) boronate is a very
Woerly, Eric M.,Struble, Justin R.,Palyam, Nagarjuna,O'Hara, Sean P.,Burke, Martin D.
p. 4333 - 4343
(2011)
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A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation
Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.
Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.
p. 1597 - 1603
(2020/02/05)

Novel resveratrol derivatives have diverse effects on the survival, proliferation and senescence of primary human fibroblasts
Resveratrol alters the cytokinetics of mammalian cell populations in a dose dependent manner. Concentrations above 25–50 μM typically trigger growth arrest, senescence and/or apoptosis in multiple different cell types. In contrast, concentrations below 10 μM enhance the growth of log phase cell cultures and can rescue senescence in multiple strains of human fibroblasts. To better understand the structural features that regulate these effects, a panel of 24 structurally-related resveralogues were synthesised and evaluated for their capacity to activate SIRT1, as determined by an ex-vivo SIRT1 assay, their toxicity, as measured by lactate dehydrogenase release, and their effects on replicative senescence in MRC5 human fibroblasts as measured by their effects on Ki67 immunoreactivity and senescence-associated β galactosidase activity. Minor modifications to the parent stilbene, resveratrol, significantly alter the biological activities of the molecules. Replacement of the 3,5-dihydroxy substituents with 3,5-dimethoxy groups significantly enhances SIRT1 activity, and reduces toxicity. Minimising other strong conjugative effects also reduces toxicity, but negatively impacts SIRT1 activation. At 100 μM many of the compounds, including resveratrol, induce senescence in primary MRC5 cells in culture. Modifications that reduce or remove this effect match those that reduce toxicity leading to a correlation between reduction in labelling index and increase in LDH release. At 10 μM, the majority of our compounds significantly enhance the growth fraction of log phase cultures of MRC5 cells, consistent with the rescue of a subpopulation of cells within the culture from senescence. SIRT1 activation is not required for rescue to occur but enhances the size of the effect.
Birar, Vishal C.,Faragher, Richard G. A.,Ostler, Elizabeth L.,Sheerin, Angela N.
p. 817 - 826
(2020/08/17)

Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo
Phthalide is a promising chemical scaffold and has been proved to show potent anti-inflammatory efficacy. In this study, three series, total of 31 novel phthalide derivatives were designed and synthesized, their anti-inflammatory activities were screened
Chen, Liu Zeng,Wu, Jing,Li, Kang,Wu, Qian Qian,Chen, Rui,Liu, Xin Hua,Ruan, Ban Feng
(2020/08/21)

Copper-catalysed, diboron-mediated: Cis -dideuterated semihydrogenation of alkynes with heavy water
Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.
Han, Xiaowei,Hu, Jiefeng,Chen, Cheng,Yuan, Yu,Shi, Zhuangzhi
supporting information
p. 6922 - 6925
(2019/06/18)

Novel resveratrol as well as derivative synthesis method and application thereof
The invention belongs to the technical field of organic synthesis and discloses novel resveratrol as well as a derivative synthesis method and application thereof. A target product resveratrol is obtained by taking 3,5-disubstituted aniline I as a raw material through the steps of carrying out diazotization reduction to generate 3,5-disubstituted arylhydrazine II, carrying out acetylation to obtain acyl arylhydrazine III, carrying out Heck coupling under the common catalysis of transition metal palladium and copper to obtain a resveratrol derivative and finally carrying out deprotection. The invention provides an efficient synthesis method of the resveratrol. The acyl arylhydrazine is used as a novel arylation reagent and the resveratrol is stereoselectively synthesized under the catalysisof a transition metal catalyst. The method provided by the invention has the advantages of easiness for obtaining the raw material, simplicity in operation and high stereoselectivity and the invention can provides an efficient method for synthesizing the resveratrol and related derivatives.
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Paragraph 0065; 0070-0071

(2019/08/02)

Preparation method of resveratrol
The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.
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Paragraph 0035-0040

(2018/11/03)

Synthesis method of resveratrol
The invention discloses a synthesis method of resveratrol. The synthesis method comprises the steps of a preparation technology of 3,5-dibromo-4-aminotoluene, a preparation technology of 3, 5-dibromotoluene, a preparation technology of (E)-1,3-dibromo-5-(4-methoxy-styrene)benzene, a preparation technology of (E)-1,3-dimethoxy-5-(4-methoxy-styrene)benzene and a preparation technology of resveratrol. The synthesis method has the advantages of being low in raw material price, less in step, high in yield and suitable for scale production.
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(2018/07/30)

Synthesis method of resveratrol
The invention provides a synthesis method of resveratrol, and belongs to the technical field of natural product synthesis. The synthesis method comprises the following steps: with 3,5-dimethoxy benzoic acid as a raw material, generating 3,5-dimethoxy benzoyl chloride (12) through an acylating chlorination reaction; generating 3,5-dimethoxy benzamide (13) through an amidation reaction of the (12);generating 3,5-dimethoxyaniline (14) through a Hofmann degradation reaction of the (13); generating 3,5-dimethoxy iodobenzene (15) through a Sandmeyer reaction on the (14); generating 3,5,4'-trimethoxy diphenylethene (31) through a reaction between the (15) and p-methoxystyrene (23), and performing demethylation of the (31) to finally obtain resveratrol (1), wherein total yield is 23.3%. Accordingto the method, the adopted reagent is cheap and easily available, aftertreatment is simple, and two expensive intermediates for Heck reaction are synthesized by adopting cheap raw materials. A new synthesis method is provided for synthesizing resveratrol.
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(2018/05/03)

Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction
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.]
Srivastava, Vivek
p. 693 - 703
(2017/03/08)

Green hydroselenation of aryl alkynes: Divinyl selenides as a precursor of resveratrol
A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60°C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.
Perin, Gelson,Barcellos, Angelita M.,Luz, Eduardo Q.,Borges, Elton L.,Jacob, Raquel G.,Lenard?o, Eder J.,Sancineto, Luca,Santi, Claudio
(2017/03/08)

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn
Moodie, Lindon W. K.,Trepos, Rozenn,Cervin, Gunnar,Brathen, Kari Anne,Lindgard, Bente,Reiersen, Rigmor,Cahill, Patrick,Pavia, Henrik,Hellio, Claire,Svenson, Johan
supporting information
p. 2001 - 2011
(2017/08/04)

Synthesis of trans-resveratrol using modified Julia olefination route
Bioactive hydroxystilbinoid-trans-resveratrol [(E)-3,5,4′ trihydroxy stilbene, 1] has been synthesized by modified Julia olefination method. The reaction between corresponding carbanion of benzothiazol-2-yl sulfone derivative and p-anisaldehyde dimethyl acetal with sodium hydride as a base, affords mainly cis-3,5,4′ trimethoxystilbene 10b with minor quantity of trans-isomev. Both the isomers have been separated in pure form and confirmed by their NMR spectral data. Demethylation of cis-3,5,4′ trimethoxystilbene either with AlCVpyridine or AlCl3/triethylamine results in the formation of trans-resveratrol.
Shenvi, Suvarna,Shivanna, Shivaprakash,Reddy, G. Chandrasekara
p. 1035 - 1038
(2017/11/10)

Method for preparing resvertrol (by machine translation)
The invention discloses method for preparing resvertrol, in order to 3,5-dimethoxy-methanol as the raw material, through chloropivaloyl, to obtain 3,5-dimethoxy oxygen radical chlorine animal pen, through the 3,5-dimethylbenzaldehyde by oxygen radical chlorine animal pen 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works. This invention, through the triphosgene 3,5-dimethoxy-methanol chloropivaloyl, instead of ethanol using sodium hydride and sodium, synthetic 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works, preparation method has high yield, low cost. (by machine translation)
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Paragraph 0027; 0028; 0033

(2016/10/31)

TRPA1 channels as targets for resveratrol and related stilbenoids
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.
Nalli, Marianna,Ortar, Giorgio,Moriello, Aniello Schiano,Morera, Enrico,Di Marzo, Vincenzo,De Petrocellis, Luciano
p. 899 - 902
(2016/05/24)

Convenient One-Step Synthesis of Benzo[c]phenanthridines by Three-Component Reactions of Isochromenylium Tetrafluoroborates and Stilbenes in Acetonitrile
A new type of three-component reaction of air-stable isochromenylium tetrafluoroborates with electron-rich stilbenes in acetonitrile has been developed under catalyst-free conditions in this work. This cascade multibond-formation reaction is initiated by an intermolecular oxa [4 + 2]-cycloaddition, relayed with a nucleophilic addition of acetonitrile, and terminated by an intramolecular Friedel-Crafts reaction, affording the corresponding benzo[c]phenanthridine analogues in one step.
Chen, Gang-Gang,Wei, Jun-Qiang,Yang, Xiaoliang,Yao, Zhu-Jun
supporting information
p. 1502 - 1505
(2016/05/02)

Design and synthesis of resveratrol-salicylate hybrid derivatives as CYP1A1 inhibitors
Resveratrol and aspirin are known to exert potential chemopreventive effects through modulation of numerous targets. Considering that the CYP450 system is responsible for the activation of environmental procarcinogens, the aim of this study was to design a new class of hybrid resveratrol-aspirin derivatives possessing the stilbene and the salicylate scaffolds. Using HepG2 cells, we evaluated (a) the inhibition of TCDD-mediated induction of CYP1A1 exerted by resveratrol-aspirin derivatives using the EROD assay, and (b) CYP1A1 mRNA in vitro. We observed significant inhibition (84%) of CYP1A1 activity and a substantial decrease in CYP1A1 mRNA with compound 3, compared to control. Resveratrol did not exert inhibition under the same experimental conditions. This inhibitory profile was supported by docking studies using the crystal structure of human CYP1A1. The potential effect exerted by compound 3 (the most active), provide preliminary evidence supporting the design of hybrid molecules combining the chemical features of resveratrol and aspirin.
Aldawsari, Fahad S.,Elshenawy, Osama H.,El Gendy, Mohamed A. M.,Aguayo-Ortiz, Rodrigo,Baksh, Shairaz,El-Kadi, Ayman O. S.,Velázquez-Martínez, Carlos A.
p. 884 - 895
(2015/11/09)

A new synthesis of resveratrol
Resveratrol was synthesized in a 4-step synthesis using a simple Sonogashira type reaction with 93% yield using commercially available 3,5-dimethoxy-1-ethynyl-benzene and 4-iodoanisole, followed by reduction, isomerization, and deprotection and with an overall yield of 63%.
Lara-Ochoa, Francisco,Sandoval-Minero, Leticia C.,Espinosa-Pérez, Georgina
p. 5977 - 5979
(2015/10/28)

Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues
Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants.
Ding, De-Jun,Cao, Xiao-Yan,Dai, Fang,Li, Xiu-Zhuang,Liu, Guo-Yun,Lin, Dong,Fu, Xing,Jin, Xiao-Ling,Zhou, Bo
p. 1011 - 1019
(2012/11/07)

Hydroxyl substitutional effect on selective synthesis of CIS, trans stilbenes and 3-arylcoumarins through perkin condensation
The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%). Copyright Taylor & Francis Group, LLC.
Xiao, Chun-Fen,Zou, Yong,Du, Jian-Li,Sun, Hong-Yi,Liu, Xian-Ke
p. 1243 - 1258
(2012/04/04)

E-selective isomerization of stilbenes and stilbenoids through reversible hydroboration
Hydroboration of a mixture of E and Z stilbenes and stilbenoids is followed by an elimination reaction to yield the E isomer with high stereoselectivity. The reaction tolerates aromatic substituents with varying stereoelectronic properties, occurs in one pot, and requires only commercially available reagents. An illustration of the isomerization reaction in a synthesis of resveratrol, a biologically active antioxidant, is presented.
Gray, Erin E.,Rabenold, Lake E.,Goess, Brian C.
scheme or table
p. 6177 - 6179
(2011/12/01)

Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors
Several analogs of gigantol (1) were synthesized to evaluate their effect on the complexes Ca2+-calmodulin (CaM) and Ca2+-CaM-CaM sensitive phosphodiesterase 1 (PDE1). The compounds belong to four structural groups including, 1,2-dip
Reyes-Ramírez, Adelfo,Leyte-Lugo, Martha,Figueroa, Mario,Serrano-Alba, Trinidad,González-Andrade, Martín,Mata, Rachel
experimental part
p. 2699 - 2708
(2011/07/08)

Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes
Resveratrol is a polyphenol isolated from many natural sources including grapes, mulberries, eucalyptus, spruce, lilies, and peanuts. The hydroxyl groups in polyphenols can be substituted with various functional groups, allowing production of multiple derivatives. NMR spectroscopy is used to identify new derivatives. Since the complete NMR data of the known derivatives can be useful for identification of the newly isolated derivatives, here, we report the synthesis of 14 methoxylated stilbenes and four 1,2-diphenylethanes and their NMR data.
Jo, Geunhyeong,Hyun, Jiye,Hwang, Doseok,Lee, Young Han,Koh, Dongsoo,Lim, Yoongho
scheme or table
p. 374 - 377
(2011/12/04)

PROCESS FOR THE PRODUCTION OF SUBSTITUTED ELECTRON RICH DIPHENYLACETYLENES
The present invention relates to an improved process of production of substituted diphenylacetylenes (tolanes) of formula (I) which are starting materials for production of stilbenes products.
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Page/Page column 11

(2011/02/24)

3,4,4′-Trihydroxy-trans-stilbene, an analogue of resveratrol, is a potent antioxidant and cytotoxic agent
Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a naturally occurring polyphenol widely distributed in food and dietary plants. This phytochemical has been intensively studied as an efficient antioxidant and anticancer agent, and a variety of substituted stilbenes have been developed in order to improve the potency of resveratrol. In this work, we described the synthesis of 3,4,4-trihydroxy-trans-stilbene (3,4,4′-THS), an analogue of resveratrol, and studied its antioxidant and cytotoxic activity in vitro. 3,4,4-THS was much more efficient than resveratrol in protecting against free radical-induced lipid peroxidation, photo-sensitized DNA oxidative damage, and free radical-induced hemolysis of human red blood cells. More potent growth inhibition in cultured human leukemia cells (HL-60) was also observed for 3,4,4-THS. The relationship between the antioxidant efficiency and cytotoxic activity was discussed, with the emphasis on inhibition of the free radical enzyme ribonucleotide reductase by antioxidants. The result that this subtle structure modification of resveratrol drastically improves its bioactivity provides important strategy to develop novel resveratrol-based molecules.
Cai, Wenqing,Zhang, Liangwei,Song, Yanlin,Zhang, Baoxin,Cui, Xuemei,Hu, Guanming,Fang, Jianguo
p. 1379 - 1387
(2012/07/31)

Efficient synthesis of natural polyphenolic stilbenes: Resveratrol, piceatannol and oxyresveratrol
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.
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)

Diversity-oriented synthesis of disubstituted alkenes using masked silanols
(Figure presented) The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and α-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.
Sore, Hannah F.,Blackwell, David T.,MacDonald, Simon J. F.,Spring, David R.
supporting information; experimental part
p. 2806 - 2809
(2010/09/04)

ZWITTERIONIC PHOSPHONIUM SALTS
A zwitterionic phosphonium salt of Formula I: wherein n is 0 or 1; R is H or SO3-; R' is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, phenyl, substituted phenyl, benzyl and C1-C10 alkoxycarbonyl; R' is CX3 when n is O; and X is selected from the group consisting of F, Cl, Br and I. The zwitterionic phosphonium salts are useful reagents for the preparation of alkenes and acetals from the corresponding aldehyde.
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Page/Page column 16; 25

(2010/04/03)

Structural determinants of resveratrol for cell proliferation inhibition potency: Experimental and docking studies of new analogs
Resveratrol is the subject of intense research because of the abundance of this compound in the human diet and as one of the most valuable natural chemopreventive agents. Further advances require new resveratrol analogs be used to identify the structural determinants of resveratrol for the inhibition potency of cell proliferation by comparing experimental and docking studies. Therefore, we synthesized new trans/(E)- and cis/(Z)-resveratrol - analogs not reported to date - by modifying the hydroxylation pattern of resveratrol and a double bond geometry. We included them in a larger panel of 14 molecules, including (Z)-3,5,4′-trimethoxystilbene, the most powerful molecule that is used as reference. Using a docking model complementary to experimental studies on the proliferation inhibition of the human colorectal tumor SW480 cell line, we show that methylation is the determinant substitution in inhibition efficacy, but only in molecules bearing a Z configuration. Most of the synthetic methylated derivatives (E or Z) stop mitosis at the M phase and lead to polyploid cells, while (E)-resveratrol inhibits cells at the S phase. Docking studies show that almost all of the docked structures of (Z)-polymethoxy isomers, but not most of the (E)-polymethoxy isomers substantially overlap the docked structure of combretastatin A-4, taken as reference ligand at the colchicine-tubulin binding site.
Mazué, Frédéric,Colin, Didier,Gobbo, Jessica,Wegner, Maria,Rescifina, Antonio,Spatafora, Carmela,Fasseur, Dominique,Delmas, Dominique,Meunier, Philippe,Tringali, Corrado,Latruffe, Norbert
experimental part
p. 2972 - 2980
(2010/08/22)

Wittig-type olefination of alcohols promoted by nickel nanoparticles: Synthesis of polymethoxylated and polyhydroxylated stilbenes
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.
Alonso, Francisco,Riente, Paola,Yus, Miguel
supporting information; experimental part
p. 6034 - 6042
(2010/02/28)

Synthesis of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles
A novel synthesis of resveratrol, DMU-212 and analogues is presented using benzyl alcohols as phosphorus ylide partners in a one-pot Wittig-type olefination reaction promoted by nickel nanoparticles.
Alonso, Francisco,Riente, Paola,Yus, Miguel
body text
p. 3070 - 3073
(2009/10/04)

Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent
An emulsion cosmetic composition comprising at least one resveratrol derivative, an aqueous phase, and an oil phase having at and at least one oil phase structuring agent, and a method for preparing emulsions capable of delivering active resveratrol to the skin.
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(2009/07/02)

Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Silicone Surfactant
An emulsion cosmetic composition comprising at least one resveratrol derivative, an aqueous phase, and an oil phase, having at least one silicone surfactant, and a method for preparing emulsions capable of delivering active resveratrol to the skin.
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(2009/07/02)

Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
An aqueous based cosmetic composition comprising at least one resveratrol derivative and a water phase containing at least one aqueous phase structuring agent; or an emulsion composition comprising at least one water phase, at least one oil phase containing at least one nonvolatile silicone, and at least one resveratrol derivative.
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(2009/07/02)

Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
An emulsion cosmetic composition comprising at least one resveratrol derivative, a water phase, and an oil phase containing at least one linear or branched volatile or near volatile silicone and a method for delivering active resveratrol to the skin.
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(2009/07/02)

Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
An anhydrous color cosmetic composition comprising at least one resveratrol derivative and particulates; and an anhydrous emulsion skin care composition.
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(2009/07/02)

Zwitterionic phosphonium sulfonates as easily phase-separable ion-tagged wittig reagents
(Chemical Equation Presented) Zwitterionic phosphonium sulfonates 3, conveniently derived from TPPMS (1), can be used as Wittig reagents in solution. The excess reagents and byproduct TPPMSO (6) can be easily separated from the product alkenes by simple precipitation with a less polar solvent. The alkenes thus obtained were often sufficiently pure without chromatographic purification. A one-pot protocol for the synthesis of α,β-unsaturated esters has been developed and appears to be convenient.
Huo, Congde,He, Xun,Tak, Hang Chan
experimental part
p. 8583 - 8586
(2009/04/04)

PREVENTION AND TREATMENT OF COLON CANCER
Stilbene compounds for the prevention and treatment of colon cancer or colon inflammation and methods of using same are provided.
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Page/Page column 21-22

(2008/12/06)

Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARα
Pterostilbene, a naturally occurring analog of resveratrol, has previously shown PPARα activation in H4IIEC3 cells and was found to decrease cholesterol levels in animals. In this study, analogs of pterostilbene were synthesized and their ability to activ
Mizuno, Cassia S.,Ma, Guoyi,Khan, Shabana,Patny, Akshay,Avery, Mitchell A.,Rimando, Agnes M.
p. 3800 - 3808
(2008/09/21)

Process for the preparation of polyhydroxylated stilbenes via claisen condensation
The invention realates to a Process for the preparation of resveratrol, comprising the steps of a) reaction of a compound according to formula I with a compound according to formula II to form a compound according to formula III b) conversion of the compound according to formula III to a compound according to formula IV and, if necessary, c) deprotection of the compound according to formula IV.
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Page/Page column 6

(2008/06/13)

Quinone reductase induction activity of methoxylated analogues of resveratrol
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.
Zhang,Go
p. 841 - 850
(2008/02/12)

An efficient synthesis of resveratrol and a hydroxyl derivative via the Perkin reaction: Cis to trans isomerisation in a demethylation process
Two trans polyphenolic stilbenes, Resveratrol and 3,4,4′,5- trans-tetrahydroxystilbene, were prepared in three steps from 4-methoxy phenylacetic acid and methoxylated benzaldehydes via a Perkin reaction. An interesting cis to trans isomerisation occured in the demethylation process in the presence of AII3 and acetonitrile to give resveratrol and 3,4,4′,5-trans-tetrahydroxystilbene with overall yields of 51% and 48% respectively.
Li, Guoxing,Zouand, Yong,Zhang, Xuejing
p. 657 - 659
(2008/09/17)

2-Amino and 2′-aminocombretastatin derivatives as potent antimitotic agents
A novel series of 2-amino and 2′-aminocombretastatin derivatives were synthesized and evaluated for antitumor activity. Several compounds had excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 11, 20, and 21 with ICsu
Chang, Jang-Yang,Yang, Ming-Fang,Chang, Chi-Yen,Chen, Chi-Ming,Kuo, Ching-Chuan,Liou, Jing-Ping
p. 6412 - 6415
(2007/10/03)

STILBENES AND CHALCONES FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES
The present disclosure provides non-naturally occurring polyphenol compounds that upregulate the expression of Apolipoprotein A-I (ApoA-I). The disclosed compositions and methods can be used for treatment and prevention of cardiovascular disease and related disease states, including cholesterol or lipid related disorders, such as, e.g., atherosclerosis.
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(2015/06/03)

Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers
New carbon-11 and fluorine-18 labeled stilbene derivatives, cis-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]8a), cis-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]8b), trans-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]10a), trans-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]10b), cis-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]12a), and trans-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]13a), were designed and synthesized as potential PET probes for aryl hydrocarbon receptor (AhR) in cancers.
Gao, Mingzhang,Wang, Min,Miller, Kathy D.,Sledge, George W.,Hutchins, Gary D.,Zheng, Qi-Huang
p. 5767 - 5772
(2007/10/03)

Stilbene-based anticancer agents: Resveratrol analogues active toward HL60 leukemic cells with a non-specific phase mechanism
Several stilbenes, related to known resveratrol, have been synthesized and tested for their anticancer effect on HL60 leukemia cell line, taking particular care of the cell cycle analysis. The most potent compound was the known (Z)-3,4′,5-trimethoxystilbe
Simoni, Daniele,Roberti, Marinella,Invidiata, Francesco Paolo,Aiello, Enrico,Aiello, Stefania,Marchetti, Paolo,Baruchello, Riccardo,Eleopra, Marco,Di Cristina, Antonietta,Grimaudo, Stefania,Gebbia, Nicola,Crosta, Lucia,Dieli, Francesco,Tolomeo, Manlio
p. 3245 - 3248
(2007/10/03)

3,5-Bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination
3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 7 have been employed in the Julia-Kocienski olefination reaction with carbonyl compounds. Sulfones 7 are readily prepared in high yields (64-97%) from commercially available 3,5-bis(trifluoromethyl)thiophenol through an alkylation/oxidation two-step sequence. The stability of metalated BTFP sulfones has been studied and compared with heteroaryl benzothiazol-2-yl (BT), 1-phenyl-1H-tetrazol-5-yl (PT), and 1-tert-butyl-1H-tetrazol-5-yl (TBT) sulfones 9-11 under different reaction conditions. The Julia-Kocienski olefination between alkyl BTFP sulfones 7 and a wide variety of aldehydes affords the corresponding 1,2-disubstituted alkenes and dienes in good yields and stereoselectivities. This one-pot protocol can be performed using KOH at room temperature or the phosphazene bases P2-Et and P4-t-Bu at -78 °C or rt and has been successfully used in a high-yielding and stereoselective synthesis of various methoxylated stilbenes such as trimethylated resveratrol. These new reaction conditions for the Julia-Kocienski olefination reaction have been also studied with BT, PT, and TBT sulfones, giving poorer results. Methylenation of aliphatic and aromatic aldehydes, ketones, and 1,2-dicarbonyl compounds is carried out through the modified Julia olefination using BTFP methyl sulfone 7d to give terminal alkenes and dienes. Mechanistic studies of the olefination reaction between benzyl BTFP sulfone 7a and aromatic aldehydes performed by KOH-induced Smiles rearrangement of stereodefined syn- and anit-β-hydroxyalkyl BTFP sulfones indicate that the stereocontrol of the reaction is determined in the elimination step. 2005 American Chemical Society.
Alonso, Diego A.,Fuensanta, Monica,Najera, Carmen,Varea, Montserrat
p. 6404 - 6416
(2007/10/03)

The photochemistry of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethyl ethanoate in alcohol solvents: A search for carbocation rearrangements
The photochemistry of the title compound 1 in methanol and 2,2,2-trifluoroethanol has been examined. In both solvents two ether products were obtained: one (18) resulting from trapping of the carbocation 2 (expected from photosolvolysis of 1), and the other (19) from the carbocation 3 (expected after rearrangement by hydride migration of cation 2). The substituted trans- and cis-stilbene derivatives 20 and 21 were also primary pbotoproducts. Analysis of product yields as a function of time revealed that the ether product 19 was formed by secondary photolysis of the stilbene derivatives, presumably by a pathway involving excited state protonation. Nanosecond laser flash photolysis results demonstrated that substituted trans-stilbene 20 was produced on the same time scale as the laser pulse.
Roberts,Pincock
p. 709 - 722
(2007/10/03)

A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids
A re-investigation of resveratrol synthesis by Perkins reaction allowed to improve this method and to determine the configuration of the intermediates. The results were applied to the synthesis of several aryl cinnamic acids for biological evaluation.
Solladié, Guy,Pasturel-Jacopé, Yacine,Maignan, Jean
p. 3315 - 3321
(2007/10/03)

Generation of phosphoranes derived from phosphites. A new class of phosphorus ylides leading to high E selectivity with semi-stabilizing groups in Wittig Olefinations
Tosylhydrazones derived from aryl aldehydes react with t-BuOK, ClFeTPP, (MeO)3P, and aldehydes to furnish olefins with high E selectivity. These reactions occur through a Wittig-type pathway via the corresponding diazo compounds, metal carbenes and phosphorous ylides, with the water-soluble trimethyl phosphate as the byproduct. Similar reactions can also be performed using ethyl diazoacetate; however, high E selectivity was only observed in the presence of LiBr. In this case, the reaction is believed to occur via the phosphonate anion, formed through an Arbuzov reaction. Thus this olefination reaction occurs through a Horner-Wadsworth-Emmons (HWE) reaction but the phosphonate anion is generated under completely base-free conditions. Copyright
Aggarwal, Varinder K.,Fulton, J. Robin,Sheldon, Chris G.,De Vicente, Javier
p. 6034 - 6035
(2007/10/03)