61240-22-0Relevant academic research and scientific papers
The stilbene and dibenzo[b,f]oxepine derivatives as anticancer compounds
Borys, Filip,Garbicz, Damian,Grzesiuk, El?bieta,Krawczyk, Hanna,Marcinkowski, Micha?,Pil?ys, Tomasz,Potera?a, Marcin,Tobiasz, Piotr
, (2019/12/26)
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.
Method for preparing trans-diphenylethylene compound
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Paragraph 0070; 0071; 0082; 0083; 0107, (2017/09/01)
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.
E-Stilbene derivatives synthesized by stereoselective reductive coupling of benzylic gem-dibromide promoted by Cu/polyamine
Cao, Hua,Wang, Qi
, p. 2703 - 2706 (2017/06/23)
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.
Ruthenium nanoparticle-intercalated montmorillonite clay for solvent-free alkene hydrogenation reaction
Upadhyay, Praveenkumar,Srivastava, Vivek
, p. 740 - 745 (2015/02/05)
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.
Catalytic wittig reactions of semi- and nonstabilized ylides enabled by ylide tuning
Coyle, Emma E.,Doonan, Bryan J.,Holohan, Andrew J.,Walsh, Killian A.,Lavigne, Florie,Krenske, Elizabeth H.,O'Brien, Christopher J.
, p. 12907 - 12911 (2016/02/18)
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.
Chemical modifications of resveratrol for improved protein kinase C alpha activity
Das, Joydip,Pany, Satyabrata,Majhi, Anjoy
experimental part, p. 5321 - 5333 (2011/10/13)
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.
Solid-Phase Reactive Chromatography (SPRC): A new methodology for wittig and horner-emmons reactions on a column under microwave irradiation
Dakdouki, Saada C.,Villemin, Didier,Bar, Nathalie
experimental part, p. 333 - 337 (2010/04/02)
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.
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 of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles
Alonso, Francisco,Riente, Paola,Yus, Miguel
body text, p. 3070 - 3073 (2009/10/04)
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.
Stilbene derivatives and their use in medicaments
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, (2008/06/13)
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
