- Vinyl-Stilbene Compounds and Uses Thereof
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The present invention relates to a biphenyl - stilbene (Vinyl-stilbene) - based compound and a pharmaceutical composition for preventing or treating norovirus infection comprising the same as an active ingredient. The present invention can be usefully used as a pharmaceutical composition for treating norovirus infection by showing superior norovirus inhibitory activity and lower cell toxicity as compared to previously known compounds.
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Paragraph 0188; 0189; 0194; 0195; 0255-0259; 0263
(2021/06/22)
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- Selenenate Anions (PhSeO?) as Organocatalyst: Synthesis of trans-Stilbenes and a PPV Derivative
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The selenenate anion (RSeO?) is introduced as an active organocatalyst for the dehydrohalogen coupling of benzyl halides to form trans-stilbenes. It is shown that RSeO? is a more reactive catalyst than the previously reported sulfur analogues (sulfenate anion, RSO?) and selenolate anions (RSe?) in the aforementioned reaction. This catalytic system was also applied to the benzylic-chloromethyl-coupling polymerization (BCCP) of a bis-chloromethyl arene to form ppv (poly(p-phenylene vinylene))-type polymers with high yields, Mn (average molecular weight) up to 13,000 and ? (dispersity) of 1.15. (Figure presented.).
- Zheng, Zhipeng,Trofymchuk, Oleksandra S.,Kurogi, Takashi,Varela, Elena,Mindiola, Daniel J.,Walsh, Patrick J.
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supporting information
p. 659 - 666
(2020/01/02)
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- Photoinitiated carbonyl-metathesis: Deoxygenative reductive olefination of aromatic aldehydes: Via photoredox catalysis
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Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the CC bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.
- Wang, Shun,Lokesh, Nanjundappa,Hioe, Johnny,Gschwind, Ruth M.,K?nig, Burkhard
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p. 4580 - 4587
(2019/05/14)
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- Identification of novel non-nucleoside vinyl-stilbene analogs as potent norovirus replication inhibitors with a potential host-targeting mechanism
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Norovirus (NV), is the most common cause of acute gastroenteritis worldwide. To date, there is no specific anti-NV drug or vaccine to treat NV infections. In this study, we evaluated the inhibitory effect of different stilbene-based analogs on RNA genome replication of human NV (HNV) using a virus replicon-bearing cell line (HG23). Initial screening of our in-house chemical library against NV led to the identification of a hit containing stilbene scaffold 5 which on initial optimization gave us a vinyl stilbene compound 16c (EC50 = 4.4 μM). Herein we report our structure-activity relationship study of the novel series of vinyl stilbene analogs that inhibits viral RNA genome replication in a human NV-specific manner. Among these newly synthesized compounds, several amide derivatives of vinyl stilbenes exhibited potent anti-NV activity with EC50 values ranging from 1 to 2 μM. A trans-vinyl stilbenoid with an appended substituted piperazine amide (18k), exhibited potent anti-NV activity and also displayed favorable metabolic stability. Compound 18k demonstrated an excellent safety profile, the highest suppressive effect, and was selective for HNV replication via a viral RNA polymerase-independent manner. Its potential host-targeting antiviral mechanism was further supported by specific activation of heat shock factor 1-dependent stress-inducible pathway by 18k. These results suggest that 18k might be a promising lead compound for developing novel NV inhibitors with the novel antiviral mechanism.
- Harmalkar, Dipesh S.,Lee, Sung-Jin,Lu, Qili,Kim, Mi Il,Park, Jaehyung,Lee, Hwayoung,Park, Minkyung,Lee, Ahrim,Lee, Choongho,Lee, Kyeong
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- Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
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Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two-step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model-aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene. (Figure presented.).
- Barlow, Helen,Buser, Jonas Y.,Glauninger, Hendrik,Luciani, Carla V.,Martinelli, Joseph R.,Oram, Niall,Thompson-Van Hook, Nichole,Richardson, Jeffery
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p. 2678 - 2690
(2018/06/04)
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- One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes
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The phospha-Peterson reaction between a lithiated secondary phosphane, MesP(Li)TMS, and an aldehyde affords Mes-phosphaalkenes which, upon methanol addition and P-oxidation, react with a second carbonyl compound site specifically to produce unsymmetric alkenes. The E/Z selectivity of the one-pot cross coupling is largely determined by the electronic nature of the aryl substituent of the first aldehyde, with electron-donating groups giving rise to increased amounts of Z-alkenes.
- Arkhypchuk, Anna I.,D'Imperio, Nicolas,Ott, Sascha
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supporting information
p. 5086 - 5089
(2018/09/13)
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- Intramolecular energy transfer and photoisomerization in stilbene dendrimers
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Stilbene dendrimers with energy harvesting chromophores, such as naphthalene and benzophenone, have been prepared and their photochemical and photophysical properties have been examined. These dendrimers underwent trans-cis mutual photoisomerization on excitation of the core stilbene or the peripheral naphthalene and benzophenone chromophores through several energy transfer processes, and photophysical processes such as intersystem crossing finally resulted in cis-trans isomerization of the core stilbene.
- Taima, Masahiro,Ishida, Yuka,Arai, Tatsuo
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supporting information
p. 1013 - 1023
(2017/09/07)
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- An effective Pd nanocatalyst in aqueous media: Stilbene synthesis by Mizoroki-Heck coupling reaction under microwave irradiation
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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.
- García, Carolina S.,Uberman, Paula M.,Martín, Sandra E.
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p. 1717 - 1727
(2017/09/27)
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- Convenient One-Step Synthesis of Benzo[c]phenanthridines by Three-Component Reactions of Isochromenylium Tetrafluoroborates and Stilbenes in Acetonitrile
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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
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supporting information
p. 1502 - 1505
(2016/05/02)
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- Anticancer Evaluation of 3,4,5,4'-trans-tetramethoxystilbene (DMU-212) and Its Analogs Against an Extensive Panel of Human Tumor Cell Lines
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DMU-212, a methoxylated resveratrol analog, has significant anticancer activity, and selectively targets tumor cells. A library of E-diarylstilbenes structurally related to DMU-212 has been synthesized and evaluated for anticancer activity against a large
- Madadi, Nikhil Reddy,Crooks, Peter Anthony
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p. 521 - 528
(2016/03/22)
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- Synthesis and biological evaluation of novel gigantol derivatives as potential agents in prevention of diabetic cataract
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As a continuation of our efforts directed towards the development of natural anti-diabetic cataract agents, gigantol was isolated from Herba dendrobii and was found to inhibit both aldose reductase (AR) and inducible nitric oxide synthase (iNOS) activity, which play a significant role in the development and progression of diabetic cataracts. To improve its bioefficacy and facilitate use as a therapeutic agent, gigantol (compound 14f) and a series of novel analogs were designed and synthesized. Analogs were formulated to have different substituents on the phenyl ring (compounds 4, 5, 8, 14a-e), substitute the phenyl ring with a larger steric hindrance ring (compounds 10, 17c) or modify the carbon chain (compounds 17a, 17b, 21, 23, 25). All of the analogs were tested for their effect on AR and iNOS activities and on D-galactose-induced apoptosis in cultured human lens epithelial cells. Compounds 5, 10, 14a, 14b, 14d, 14e, 14f, 17b, 17c, 23, and 25 inhibited AR activity, with IC50 values ranging from 5.02 to 288.8 μM. Compounds 5, 10, 14b, and 14f inhibited iNOS activity with IC50 ranging from 432.6 to 1188.7 μM. Compounds 5, 8, 10, 14b, 14f, and 17c protected the cells from D-galactose induced apoptosis with viability ranging from 55.2 to 76.26%. Of gigantol and its analogs, compound 10 showed the greatest bioefficacy and is warranted to be developed as a therapeutic agent for diabetic cataracts.
- Wu, Jie,Lu, Chuanjun,Li, Xue,Fang, Hua,Wan, Wencheng,Yang, Qiaohong,Sun, Xiaosheng,Wang, Meiling,Hu, Xiaohong,Chen, C.-Y. Oliver,Wei, Xiaoyong
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- Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition
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A small library of polymethoxystilbene glycosides (20-25) related to the natural polyphenol resveratrol have been synthesized and subjected, together with their aglycones 17-19, to an antiproliferative activity bioassay toward Caco-2 and SH-SY5Y cancer cells. Six of the compounds exhibit antiproliferative activity against at least one cell line. In particular, compounds 17 and 18 proved highly active on at least one of the two cell cultures. Compound 18 showed a GI50 value of 3 ΜM against Caco-2 cells, a value comparable to that of the anticancer drug 5-fluorouracil. The closely related compound 19 proved inactive, and its conjugates 22 and 25 showed weak cell growth inhibition. The results indicate that minimal differences in the structure of both polymethoxystilbenes and their glycosides can substantially affect the antiproliferative activity. The possible hydrolytic release of the aglycones 17-19 by β-glucosidase or β-galactosidase was also evaluated. Compounds 20-25 were also tested as potential β-glucosidase, β-galactosidase, and α-glucosidase inhibitors. A promising inhibitory activity toward α-glucosidase was observed for 21 (IC50 = 78 ΜM) and 25 (IC50 = 70 ΜM), which might be indicative of their potential as lead compounds for development of antidiabetic or antiobesity agents.
- Cardullo, Nunzio,Spatafora, Carmela,Musso, Nicolò,Barresi, Vincenza,Condorelli, Daniele,Tringali, Corrado
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p. 2675 - 2683
(2015/12/09)
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- RESVERATROL-BASED COMPOUNDS
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The invention provides a compound having the structure compound having the structure: Formula wherein bond a is present or absent, wherein when bond a is absent, then bond β is: Sign (I) and R1 is: Formula and when bond a is present, then Rsub
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- Synthesis of pterostilbene by julia olefination
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A simple, E-stereoselective route for the synthesis of the biologically active compounds trans-pterostilbene and tetramethoxy stilbene from the readily available starting materials 3,5-dimethoxy benzyl alcohol and 4-hydroxy benzaldehyde was developed using Julia olefination as a key reaction. Taylor & Francis Group, LLC.
- Peddikotla, Prabhakar,Chittiboyina, Amar G.,Khan, Ikhlas A.
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p. 3217 - 3223
(2014/01/06)
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- Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes
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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
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p. 374 - 377
(2011/12/04)
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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 novel analogues of (+)-varitriol via olefin cross-metathesis reaction
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Novel analogues of (+)-varitriol have been synthesized via olefin cross-metathesis reaction using Grubb's catalyst. Newly synthesized compounds were screened for cytotoxicity and they showed mild activity against RAW264.7 and HT29 cell lines.
- Nagarapu, Lingaiah,Paparaju, Venkateswarlu,Satyender, Apuri
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p. 2351 - 2354
(2008/09/20)
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- Couplings of benzylic halides mediated by titanocene chloride: Synthesis of bibenzyl derivatives
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Titanocene monochloride catalyzes the homocoupling of benzylic halides and benzylic gem-dibromides to give the corresponding bibenzyl and stilbenyl systems. Exposure of benzylic bromides to Ti(III) in the presence of aldehydes gave rise to the Barbier-type products. Examples of the utility of the herein described processes are included.
- Barrero, Alejandro F.,Herrador, M. Mar,Del Moral, Jose F. Quilez,Arteaga, Pilar,Akssira, Mohammed,El Hanbali, Fadwa,Arteaga, Jesus F.,Dieguez, Horacio R.,Sanchez, Elena M.
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p. 2251 - 2254
(2007/10/03)
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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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- A simple access to biologically important trans-stilbenes via Ru-catalyzed cross metathesis
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The cross metathesis of methoxy- or acetoxy-substituted styrenes using the Grubbs II catalyst affords unsymmetrical (mixed) E-stilbenes with astonishingly high selectivity (up to 79% yield). This approach offers a short and flexible synthesis of variously substituted stilbenes, which are derivatives or precursors of biologically important compounds such as resveratrol, piceatannol, and pinostilbene. Georg Thieme Verlag Stuttgart.
- Velder, Janna,Ritter, Stefanie,Lex, Johann,Schmalz, Hans-Guenther
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p. 273 - 278
(2007/10/03)
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- Synthesis of?stilbene derivatives with inhibition of?SARS coronavirus replication
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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.
- Li, Yue-Qing,Li, Ze-Lin,Zhao, Wei-Jie,Wen, Rui-Xing,Meng, Qing-Wei,Zeng, Yi
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p. 1084 - 1089
(2007/10/03)
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- 3,5-Bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination
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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
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p. 6404 - 6416
(2007/10/03)
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- Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis
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An efficient and highly stereoselective synthetic procedure is reported for the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives. The strategy rests on a cross-metathesis reaction catalyzed by stable, well-defined (alkylidene)ruthenium complexes, in particular the second-generation Grubbs catalyst [RuCl2(=CHPh)(SIMes) (PCy3)] [SIMes = 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2- ylidene]. The metathesis of unprotected phenolic styrenes is illustrated by the synthesis of the important phytoalexins (E)-3,4′,5-trihydroxystilbene (resveratrol) and (E)-3,3′,4,5′-tetrahydroxystilbene (piceatannol). Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Ferre-Filmon, Karine,Delaude, Lionel,Demonceau, Albert,Noels, Alfred F.
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p. 3319 - 3325
(2007/10/03)
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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 5
(2008/06/13)
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- Low-valent titanium mediated synthesis of hydroxystilbenoids: Some new observations
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A series of phenolic stilbenoids possessing different numbers and positions of hydroxylation, partial methoxyl substituents and nature of olefinic moieties has been synthesized by McMurry coupling. It is found that the McMurry coupling of the phenolic aldehydes furnishes the dihydrostilbenes via an in situ hydrogenation, while the phenolic ketones give the stilbenes. Interestingly, the study also reveals that the low-valent titanium reagent (TiCl 3-Zn-THF) could selectively depyranylate phenolic -OTHP function without affecting alcoholic -OTHP group.
- Shadakshari,Rele,Nayak,Chattopadhyay
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p. 1934 - 1938
(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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- Photoisomerization of stilbene dendrimers: The need for a volume-conserving isomerization mechanism
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Highly branched stilbene dendrimers were synthesized and their photochemical behavior was studied. Even the stilbene dendrimer with molecular weight over 6500 underwent transcis isomerization in the excited singlet state within the lifetime of 10 ns. The
- Uda, Mayuko,Mizutani, Takuo,Hayakawa, Junpei,Momotake, Atsuya,Ikegami, Masashi,Nagahata, Ritsuko,Arai, Tatsuo
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p. 596 - 605
(2007/10/03)
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- Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors
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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.
- Kim,Ko,Jae Eun Park,Jung,Sang Kwang Lee,Chun
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p. 160 - 164
(2007/10/03)
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- Bis-, tris-, and tetrakis(squaraines) linked by stilbenoid scaffolds
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The oligosquaraines 1-5, with stilbenoid scaffolds, were prepared by multistep syntheses in which the final steps consisted of condensation reactions between the semisquaric acid 21 and multiple resorcinols 12b-15b and 17b. The target compounds exhibit in
- Gerold, Jürgen,Holzenkamp, Uta,Meier, Herbert
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p. 2757 - 2763
(2007/10/03)
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- Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2-diphenyl-1- picryhydrazyl radical
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Resveratrol (3,4',5-trihydroxy-trans-stilbene), an antioxidant from grapes, and five other polyhydroxystilbenes were synthesized. Their antioxidative properties were evaluated in two model systems [pure lipid oxidation using the Rancimat method and 2,2-diphenyl-1-picryhydrazyl (DPPH) free radical scavenging model.] 3,3',4,5'-Tetrahydroxystilbene, 3,3',4,5,5'- pentahydroxystilbene, and 3,4,4',5-tetrahydroxystilbene were found to be more active than resveratrol in both models. A dimer of resveratrol was identified as the major radical reaction product when resveratrol was reacted with DPPH radicals.
- Wang, Mingfu,Jin, Yi,Ho, Chi-Tang
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p. 3974 - 3977
(2007/10/03)
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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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