- The stilbene and dibenzo[b,f]oxepine derivatives as anticancer compounds
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In the present study, the synthesis and cytotoxic effect of six stilbenes and three oxepine derivatives against two cancerous – HeLa and U87, and two normal – EUFA30 and HEK293 cell lines has been reported. The results of cytotoxic assay and flow cytometry analysis revealed that compounds 9-nitrobenzo[b]naphtho[1,2-f]oxepine (4), (E)-3,3′,4,4′,5,5′-hexamethoxystilbene (6) and 4-hydroxy-2′,4′-dinitrostilbene (8) were the most active and their interaction with tubulin (crystal structure from PDB) has been analyzed by computer molecular modeling. Molecular docking of these compounds on colchicine binding site of the tubulin indicates the interaction of (4), (6) and (8) with tubulin. The compound (4) could interact stronger with tubulin, relative to colchicine, however, with no selectivity of action against cancer and normal cells. Conversely, compounds (6) and (8) interact more weakly with tubulin, relative to colchicine but they act more selectively towards cancerous versus normal cell lines. Obtained results proved that the compounds that are the most active against cancerous cells operate through tubulin binding.
- Borys, Filip,Garbicz, Damian,Grzesiuk, El?bieta,Krawczyk, Hanna,Marcinkowski, Micha?,Pil?ys, Tomasz,Potera?a, Marcin,Tobiasz, Piotr
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- Method for preparing trans-diphenylethylene compound
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The invention relates to a preparation method of organic compounds and provides a method for preparing a trans-diphenylethylene compound. The method comprises adding a gem-dibromomethyl aromatic hydrocarbon compound, copper and polyamine into a reactor in the presence of a solvent, carrying out deoxidizing treatment, adding an oxygen-free water-free solvent into the reactor, carrying out a coupling reaction process to obtain C-C- double bonds, and carrying out separation and purification to obtain the trans-diphenylethylene compound. The method has mild synthesis conditions and has good reaction compatibility to different functional groups. The gem-dibromomethyl aromatic hydrocarbon compound as a raw material is easy to synthesize, may have different substituent groups and has a variable structure. The product obtained by coupling a raw material can be simply treated and has high purity. The asymmetric trans-diphenylethylene compound can be prepared from two different raw materials.
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Paragraph 0096; 0097; 0098; 0099; 0100; 0101; 0107
(2017/09/01)
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- E-Stilbene derivatives synthesized by stereoselective reductive coupling of benzylic gem-dibromide promoted by Cu/polyamine
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Stereoselective reductive coupling reaction of benzylic gem-dibromide promoted by Cu/polyamine produces E-stilbene derivatives with high yield under mild conditions. It provides a short pathway to synthesize symmetrical and asymmetrical E-stilbene derivatives using cheap reagents and alkenyl-free starting material together with easy workup.
- Cao, Hua,Wang, Qi
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p. 2703 - 2706
(2017/06/23)
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- Ruthenium nanoparticle-intercalated montmorillonite clay for solvent-free alkene hydrogenation reaction
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Well-characterized, ruthenium nanoparticle-intercalated montmorillonite clay was used as a catalyst in solvent-free alkene hydrogenation reactions and the corresponding products were obtained in good yields. The catalytic activity of ruthenium nanoparticle-intercalated montmorillonite clay was successfully tested with 16 different functionalized and non-functionalized alkenes. Apart from alkene reduction, the ruthenium nanoparticle-intercalated montmorillonite clay was also tested in Wittig-type reactions for obtaining dehydrobrittonin A, an important intermediate for the synthesis of brittonin A. Ruthenium nanoparticle-intercalated montmorillonite clay was found to be active in the synthesis of dehydrobrittonin A and brittonin A. The ability to recycle the catalyst nine times, together with low catalyst loading, high catalytic activity and catalytic selectivity were noteworthy advantages of the proposed protocol.
- Upadhyay, Praveenkumar,Srivastava, Vivek
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p. 740 - 745
(2015/02/05)
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- Catalytic wittig reactions of semi- and nonstabilized ylides enabled by ylide tuning
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The first examples of catalytic Wittig reactions with semistabilized and nonstabilized ylides are reported. These reactions were enabled by utilization of a masked base, sodium tert-butyl carbonate, and/or ylide tuning. The acidity of the ylide-forming proton was tuned by varying the electron density at the phosphorus center in the precatalyst, thus facilitating the use of relatively mild bases. Steric modification of the precatalyst structure resulted in significant enhancement of E selectivity up to >95:5, E/Z. Time for a tune up: Catalytic Wittig reactions with semi- and nonstabilized ylides were enabled by use of a masked base (NaOCO2tBu) and/or ylide tuning. The acidity of the ylide-forming proton was tuned by varying the electron density at the P center in the precatalyst, thus facilitating the use of relatively mild bases. Steric modification of the precatalyst structure resulted in significant enhancement of E selectivity.
- Coyle, Emma E.,Doonan, Bryan J.,Holohan, Andrew J.,Walsh, Killian A.,Lavigne, Florie,Krenske, Elizabeth H.,O'Brien, Christopher J.
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supporting information
p. 12907 - 12911
(2016/02/18)
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- Chemical modifications of resveratrol for improved protein kinase C alpha activity
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Resveratrol (1) is a naturally occurring phytoalexin that affects a variety of human disease models, including cardio- and neuroprotection, immune regulation, and cancer chemoprevention. One of the possible mechanisms by which resveratrol affects these disease states is by affecting the cellular signaling network involving protein kinase C alpha (PKCα). PKCα is a member of the family of serine/threonine kinases, whose activity is inhibited by resveratrol. To study the structure-activity relationship, several monoalkoxy, dialkoxy and hydroxy analogs of resveratrol have been synthesized, tested for their cytotoxic effects on HEK293 cells, measured their effects on the membrane translocation properties of PKCα in the presence and absence of the PKC activator TPA, and studied their binding with the activator binding domain of PKCα. The analogs showed less cytotoxic effects on HEK293 cells and caused higher membrane translocation (activation) than that of resveratrol. Among all the analogs, 3, 16 and 25 showed significantly higher activation than resveratrol. Resveratrol analogs, however, inhibited phorbol ester-induced membrane translocation, and the inhibition was less than that of resveratrol. Binding studies using steady state fluorescence spectroscopy indicated that resveratrol and the analogs bind to the second cysteine-rich domain of PKCα. The molecular docking studies indicated that resveratrol and the analogs interact with the protein by forming hydrogen bonds through its hydroxyl groups. These results signify that molecules developed on a resveratrol scaffold can attenuate PKCα activity and this strategy can be used to regulate various disease states involving PKCα.
- Das, Joydip,Pany, Satyabrata,Majhi, Anjoy
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experimental part
p. 5321 - 5333
(2011/10/13)
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- Solid-Phase Reactive Chromatography (SPRC): A new methodology for wittig and horner-emmons reactions on a column under microwave irradiation
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A new methodology named solid-phase reactive chromatography (SPRC), which combines reaction, separation, and purification into a single unit for the preparation of small samples, is described. This method was illustrated in the synthesis of some natural bioactive compounds, namely, methoxylated analogues of resveratrol, alkylresorcinols, and 5-aryl-2,4-pentadienoates, over a column of alumina-KF under microwave irradiation by using the Wittig and HornerEmmons reactions. This approach permitted the preparation of the target olefins with high purity and good to excellent yields in short reaction times.
- Dakdouki, Saada C.,Villemin, Didier,Bar, Nathalie
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experimental part
p. 333 - 337
(2010/04/02)
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- Wittig-type olefination of alcohols promoted by nickel nanoparticles: Synthesis of polymethoxylated and polyhydroxylated stilbenes
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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
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supporting information; experimental part
p. 6034 - 6042
(2010/02/28)
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- Synthesis of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles
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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
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body text
p. 3070 - 3073
(2009/10/04)
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- Stilbene derivatives and their use in medicaments
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The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R1 to R6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and s
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- STILBENE DERIVATIVES AND THEIR USE IN MEDICAMENTS
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The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R1 to R6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and s
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Page/Page column 6
(2008/06/13)
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- Microwave-assisted coupling of carbonyl compound: An efficient synthesis of olefin
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Self-coupling of various ketones and aldehyde as well as mixed coupling of ketones employing TiCl4/Zn under microwave irradiation has been carried out to afford the corresponding olefins.
- Ramana,Singh,Parihar
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p. 760 - 761
(2007/10/03)
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- Resveratrol analogues as selective cyclooxygenase-2 inhibitors: Synthesis and structure-activity relationship
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A series of hydroxylated and methoxylated trans-stilbenes were synthesized and evaluated for their ability to inhibit COX-1 and COX-2. Some of the hydroxylated derivatives are highly selective COX-2 inhibitor with potency comparable or better than clinically established drugs. Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is found in grapes and various medical plants. Among cytotoxic, antifungal, antibacterial cardioprotective activity resveratrol also demonstrates non-selective cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibition. In order to find more selective COX-2 inhibitors a series of methoxylated and hydroxylated resveratrol derivatives were synthesized and evaluated for their ability to inhibit both enzymes using in vitro inhibition assays for COX-1 and COX-2 by measuring PGE2 production. Hydroxylated but not methoxylated resveratrol derivatives showed a high rate of inhibition. The most potent resveratrol compounds were 3,3′,4′,5-tetra-trans-hydroxystilbene (COX-1: IC50 = 4.713, COX-2: IC50 = 0.0113 μM, selectivity index = 417.08) and 3,3′,4,4′,5,5′-hexa-hydroxy-trans-stilbene (COX-1: IC 50 = 0.748, COX-2: IC50 = 0.00104 μM, selectivity index = 719.23). Their selectivity index was in part higher than celecoxib, a selective COX-2 inhibitor already established on the market (COX-1: IC 50 = 19.026, COX-2: IC50 = 0.03482 μM, selectivity index = 546.41). Effect of structural parameters on COX-2 inhibition was evaluated by quantitative structure-activity relationship (QSAR) analysis and a high correlation was found with the topological surface area TPSA (r = 0.93). Docking studies on both COX-1 and COX-2 protein structures also revealed that hydroxylated but not methoxylated resveratrol analogues are able to bind to the previously identified binding sites of the enzymes. Hydroxylated resveratrol analogues therefore represent a novel class of highly selective COX-2 inhibitors and promising candidates for in vivo studies.
- Murias, Marek,Handler, Norbert,Erker, Thomas,Pleban, Karin,Ecker, Gerhard,Saiko, Philipp,Szekeres, Thomas,J?ger, Walter
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p. 5571 - 5578
(2007/10/03)
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- Novel resveratrol analogs
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This invention relates to novel resveratrol analogs of the formula given below; wherein R, R1, R2 and R3 are: 1. R=OH, R1=R2=R3=H; 2. R=OH, R1=Br, R2=R3=H;
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- Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes
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Selective removal of the 4-methoxy group of 3,4,5-trimethoxystilbenes was performed under electron transfer conditions from Na metal in THF. Careful control of reaction conditions and quenching procedure allowed the synthesis of either (E)-3,5-dimethoxystilbenes or 3,5-dimethoxybibenzyls.
- Azzena, Ugo,Dettori, Giovanna,Idini, Maria Vittoria,Pisano, Luisa,Sechi, Grazia
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p. 7961 - 7966
(2007/10/03)
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- NOVEL RESVERATROL ANALOGS
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This invention relates to novel resveratrol analogs of the formula given below; wherein R, R1, R2 and R3 are: 1. R=OH, R1=R2=R3=H; 2. R=0H, R1=Br, R2=R3=H;
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- Efficient synthesis of benzylphosphine oxides and E-stilbenes
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A series of substituted benzylphosphine oxides has been synthesized by reduction of the corresponding (α-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 °C, 12 h) or tributyltin hydride and AIBN (C6H6, 80 °C, 2 h). Reaction of the (α-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.
- Brown,Brown, Karen M.,Lawrence,Lawrence, Nicholas J.,Liddle,Liddle, John,Muhammad,Muhammad, Faiz,Jackson,Jackson, David A.
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p. 6733 - 6736
(2007/10/02)
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- Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization
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An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, a
- Cushman, Mark,Nagarathnam, Dhanapalan,Gopal, D.,Chakraborti, Asit K.,Lin, Chii M.,Hamel, Ernest
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p. 2579 - 2588
(2007/10/02)
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- Efficient synthesis of E-stilbenes
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A convenient, high yield, method for the synthesis of E-stilbenes (2a-f and 3) is described starting from benzyl bromides (1a-f) using LDA.
- Mali,Jagtap
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p. 841 - 848
(2007/10/02)
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- Process for the preparation of styrene derivatives and/or stilbene derivatives
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Compounds of the formulae in which Z represents unsubstituted or substituted phenyl or naphthyl, Z1 represents hydrogen or has the same meaning as Z and Z2 represents unsubstituted or substituted phenylene, naphthylene or p-biphenylene or an unsubstituted or substituted stilbene radical, can be obtained in a simple and economical manner in accordance with a novel process by reacting ethylene, under a pressure of 0.1 to 20 bar, in the presence of a base and with the addition of specific palladium catalysts, such as palladium acetate, with appropriate acid halides. The compounds of the formulae Ia and Ib are valuable intermediates, in particular for the preparation of fluorescent brighteners or scintillators.
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- SYNTHESIS OF STYRENE AND STILBENE DERIVATIVES BY THE PALLADIUM-CATALYSED ARYLATION OF ETHYLENE WITH AROYL CHLORIDES
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The arylation of ethylene with aroyl chlorides, catalysed by palladium(II) acetate, leads to styrene and stilbene derivatives.By appropriate choice of reaction conditions, particularly the ethylene pressure, the reaction can be made to produce either styrene or stilbene derivatives selectively.The reaction tolerates those common substituents which do not react with aroyl chlorides.Only trans-stilbene derivatives are formed.
- Spencer, Alwyn
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p. 117 - 122
(2007/10/02)
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- Sythesis of 2,2'-Diacyl-1,1'-biaryls. Regiocontrolled Protection of Ketones in Unsymmetrically Substituted 9,10-Phenanthrenequinones
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A regiocontrolled monoketalization of unsymmetrically substituted phenanthrenequinones by use of 2,2-dimethyl-1,3-propanediol as the ketalizing reagent has been effected with the help of bromo substitution in one of the aromatic rings at the C-1 or C-8 po
- Mervic, Miljenko,Ghera, Eugene
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p. 4720 - 4725
(2007/10/02)
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