- Detailed 1H and 13C NMR spectral data assignment for two dihydrobenzofuran neolignans
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In this work we present a complete proton (1H) and carbon 13(13C) nuclear magnetic resonance (NMR) spectral analysis of two synthetic dihydrofuran neolignans (±)-trans-dehydrodicoumarate dimethyl ester and (±)-trans-dehydrodiferulate
- Medeiros, Talita C.T.,Dias, Herbert J.,Silva, Eliane O.,Fukui, Murilo J.,Soares, Ana Carolina F.,Kar, Tapas,Heleno, Vladimir C.G.,Donate, Paulo M.,Parreira, Renato L.T.,Crotti, Ant?nio E.M.
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- Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities
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Stilbenes and benzofuran neolignans are important groups of plant phenolics therefore they play a significant role in plants and human health. The objective of this study was to investigate the structure-activity relationships of naturally occurring stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors. A series of these compounds were prepared and assessed for their inhibition on acetylcholinesterase activity. δ-Viniferin, pterostilbene trans-dehydrodimer, pallidol, grossamide, and boehmenan exerted acetylcholinesterase inhibitory potential. The several oligomeric compounds protected against cell damage resulting from t-BHP exposure and inhibited lipopolysaccharide/interferon-gamma (LPS/IFNγ)-induced NO production in vitro. Our findings highlight the great potential of pterostilbene trans-dehydrodimer, pallidol, and boehmenan as multifunctional nutraceuticals for management of neurodegenerative diseases.
- Nagumo, Mina,Ninomiya, Masayuki,Oshima, Natsuko,Itoh, Tomohiro,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
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- Synthesis of Thio-lignan Analogues, Bioequivalent Salvinal without Unfavored Aldehyde
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The oxygen in the benzofuran (BF) of three antiproliferative natural neolignans, salvinal (1), obovaten (2), and 2-[7-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran-5-yl]ethanol (3), was replaced with sulfur to form the new biological scaffold benzothioph
- Saito, Yohei,Kobayashi, Yukiko,Yoshida, Nanami,Goto, Masuo,Nakagawa-Goto, Kyoko
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- Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents
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Oxidative dimerization of ferulic acid methyl ester afforded dihydrobenzofuran derivative and new linear compound identified by X-ray crystallography. The gallate derivatized dihydrobenzofuran analogue was obtained and all compounds were evaluated for pot
- Rakotondramanana,Delomenede, Melanie,Baltas, Michel,Duran, Hubert,Bedos-Belval, Florence,Rasoanaivo, Philippe,Negre-Salvayre, Anne,Gornitzka, Heinz
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- Studies on the preparation of bioactive lignans by oxidative coupling reaction. I. Preparation and lipid peroxidation inhibitory effect of benzofuran lignans related to schizotenuins
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The parent benzofuran lignan 4 of schizotenuins 1-3 and related compounds were efficiently prepared by a judicious use of the oxidative coupling reaction, and were tested for their inhibitory effects on lipid peroxidation in rat brain homogenate and rat l
- Maeda,Masuda,Tokoroyama
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- PHENOLIC DIHYDROBENZOFURANE DERIVATIVES, MEDICAL AND COSMETIC PREPARATIONS CONTAINING THESE DERIVATIVES, AND USE THEREOF
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The invention relates to novel dihydrobenzofurane derivatives and their use as cosmetics and medicaments. These compounds possess antibacterial, anti-inflammatory and antioxidative properties. The invention relates also to compositions, preferably antibac
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Page/Page column 12-13
(2021/06/11)
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- (±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
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Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.
- Bernal, Freddy A.,Gerhards, Marcel,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
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- Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives
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The laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives using aerial oxygen as the oxidant has been developed. Depending on the substitution pattern of the vanillidene double bond of the substrate, either dilactones, dihydrobenzo[b]furans or biphenyls are formed.
- Constantin, Mihaela-Anca,Conrad, Juergen,Beifuss, Uwe
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supporting information
p. 2375 - 2379
(2013/02/21)
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- Explorations into neolignan biosynthesis: Concise total syntheses of helicterin B, helisorin, and helisterculin A from a common intermediate
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Helicterins A and B (1 and 2), helisorin (3), and helisterculin A (4) are structurally unique natural products with the ability to combat the avian myeloblastosis virus. Biogenetically, their architectures are considered to be products of seemingly straightforward Diels-Alder, radical-based, or acid-induced dimerizations of common, simpler precursors. Yet, the pursuit of such blueprints in the laboratory has failed thus far in enabling their successful synthesis. Herein, we describe the first total syntheses of three of these natural products. Key features include the use of a building block distinct from Nature's likely starting material, highly complex retro Diels-Alder/Diels-Alder reaction cascades, an unconventional protecting group to achieve the proper balance of chemical reactivity on sensitive scaffolds, and several carefully developed reactionconditions that effectively balance competing reaction pathways.
- Snyder, Scott A.,Kontes, Ferenc
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supporting information; experimental part
p. 1745 - 1752
(2009/07/25)
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- Antiangiogenic activity of synthetic dihydrobenzofuran lignans
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A series of synthetic dihydrobenzofuran lignans, obtained by biomimetic oxidative dimerization of caffeic or ferulic acid methyl ester followed by derivatization reactions, was tested for its antiangiogenic activity in the CAM (chorioallantoic membrane) a
- Apers, Sandra,Paper, Dietrich,Buergermeister, Jutta,Baronikova, Slavka,van Dyck, Stefaan,Lemiere, Guy,Vlietinck, Arnold,Pieters, Luc
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p. 718 - 720
(2007/10/03)
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- Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization
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A series of 19 related dihydrobenzofuran lignans and benzofurans was obtained by a biomimetic reaction sequence involving oxidative dimerization of p-coumaric, caffeic, or ferulic acid methyl esters, followed by derivatization reactions. All compounds were evaluated for potential anticancer activity in an in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Leukemia and breast cancer cell lines were relatively more sensitive to these agents than were the other cell lines. Compounds 2c and 2d, but especially 2b (methyl (E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3- methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate), the dimerization product of caffeic acid methyl ester, containing a 3',4'-dihydroxyphenyl moiety and a hydroxyl group in position 7 of the dihydrobenzofuran ring, showed promising activity. The average GI50 value (the molar drug concentration required for 50% growth inhibition) of 2b was 0.3 μM. Against three breast cancer cell lines, 2b had a GI50 value of 3-side chain, reduction of the methoxycarbonyl functionalities to primary alcohols, or oxidation of the dihydrobenzofuran ring to a benzofuran system resulted in a decrease or loss of cytotoxic activity. Compound 2b inhibited mitosis at micromolar concentrations in cell culture through a relatively weak interaction at the colchicine binding site of tubulin. In vitro it inhibited tubulin polymerization by 50% at a concentration of 13 ± 1 μM. The 2R,3R-enantiomer of 2b was twice as active as the racemic mixture, while the 2S,3S- enantiomer had minimal activity as an inhibitor of tubulin polymerization. These dihydrobenzofuran lignans (2-phenyl- dihydrobenzofuran derivatives) constitute a new group of antimitotic and potential antitumor agents that inhibit tubulin polymerization.
- Pieters, Luc,Van Dyck, Stefaan,Gao, Mei,Bai, Ruoli,Hamel, Ernest,Vlietinck, Arnold,Lemière, Guy
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p. 5475 - 5481
(2007/10/03)
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- 3',4-Di-O-methylcedrusin: synthesis, resolution and absolute configuration
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The title compound has been synthesised in racemic form by a biomimetic reaction sequence.The two enantiomers were resolved by column cromatography of one of the synthetic intermediates.On the basis of CD results a tentative absolute configuration for the synthetic enantiomers and natural 3',4-di-O-methylcedrusin is proposed.
- Lemiere, Guy,Gao, Mei,Groot, Alex De,Dommisse, Roger,Lepoivre, Josef,et al.
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p. 1775 - 1780
(2007/10/02)
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- Regio- and Diastereo-selective Synthesis of Dimeric Lignans Using Oxidative Coupling
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The oxidative dimerization of monolignols such as (E)-isoeugenol (1), (E)-methyl ferulate (2) and (E)-coniferyl alcohol (3) has been performed using two catalytic systems: horseradish peroxidase (HRP)-H2O2 and tetraphenylporphyrinatomanganese(III) acetate
- Chioccara, Francesco,Poli, Sonia,Rindone, Bruno,Pilati, Tullio,Brunow, Goesta,et al.
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p. 610 - 616
(2007/10/02)
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- Total Synthesis of Two Naturally Occurring Neolignans of Potential Biological Activity
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The first synthesis of the racemates of two naturally occurring neolignans, 1 and 2, was accomplished starting from methyl ferulate.
- Antus, Sandor,Gottsegen, Agnes,Kolonits, Pal,Wagner, Hildebert
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p. 593 - 594
(2007/10/02)
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- The Relative Configuration of Grossamide and Hordatines
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The phenyl group at C-7 of grossamide (1) was determined by PMR spectra to be situated in a trans relationship to the carbonyl group at C-8.It was elucidated that the hordatines (3a, 4a) also have a trans configuration.
- Yoshihara, Teruhiko,Yamaguchi, Katsuyoshi,Sakamura, Sadao
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p. 217 - 220
(2007/10/02)
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