118799-80-7Relevant articles and documents
Detailed 1H and 13C NMR spectral data assignment for two dihydrobenzofuran neolignans
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.
, p. 136 - 143 (2016)
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
Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities
Nagumo, Mina,Ninomiya, Masayuki,Oshima, Natsuko,Itoh, Tomohiro,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
, p. 2475 - 2479 (2019)
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.
Synthesis of Thio-lignan Analogues, Bioequivalent Salvinal without Unfavored Aldehyde
Saito, Yohei,Kobayashi, Yukiko,Yoshida, Nanami,Goto, Masuo,Nakagawa-Goto, Kyoko
, p. 7092 - 7106 (2021)
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
Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents
Rakotondramanana,Delomenede, Melanie,Baltas, Michel,Duran, Hubert,Bedos-Belval, Florence,Rasoanaivo, Philippe,Negre-Salvayre, Anne,Gornitzka, Heinz
, p. 6018 - 6026 (2007)
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
Studies on the preparation of bioactive lignans by oxidative coupling reaction. I. Preparation and lipid peroxidation inhibitory effect of benzofuran lignans related to schizotenuins
Maeda,Masuda,Tokoroyama
, p. 2500 - 2505 (1994)
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
PHENOLIC DIHYDROBENZOFURANE DERIVATIVES, MEDICAL AND COSMETIC PREPARATIONS CONTAINING THESE DERIVATIVES, AND USE THEREOF
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Page/Page column 12-13, (2021/06/11)
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
(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
Bernal, Freddy A.,Gerhards, Marcel,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, (2020/08/06)
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.
Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives
Constantin, Mihaela-Anca,Conrad, Juergen,Beifuss, Uwe
, p. 2375 - 2379 (2013/02/21)
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.
Explorations into neolignan biosynthesis: Concise total syntheses of helicterin B, helisorin, and helisterculin A from a common intermediate
Snyder, Scott A.,Kontes, Ferenc
supporting information; experimental part, p. 1745 - 1752 (2009/07/25)
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.
Antiangiogenic activity of synthetic dihydrobenzofuran lignans
Apers, Sandra,Paper, Dietrich,Buergermeister, Jutta,Baronikova, Slavka,van Dyck, Stefaan,Lemiere, Guy,Vlietinck, Arnold,Pieters, Luc
, p. 718 - 720 (2007/10/03)
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
