94169-63-8Relevant academic research and scientific papers
An improved synthesis of hemichrysophaentin-AB fragment of chrysophaentin A
Fullenkamp, Christopher R.,Sulikowski, Gary A.
supporting information, (2020/03/25)
Synthetic fragments of chrysophaentin A, a rare antimicrobial marine natural product, were required to support structure-activity and mechanism of action studies. Hemichrysophaentin, a synthetic fragment of chrysophaentin A showed antimicrobial activity a
Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2
St. John, Sarah E.,Jensen, Katherine C.,Kang, Soosung,Chen, Yafang,Calamini, Barbara,Mesecar, Andrew D.,Lipton, Mark A.
, p. 6022 - 6037 (2013/09/23)
Resveratrol (3,5,4′-trihydroxylstilbene) has been proposed to elicit a variety of positive health effects including protection against cancer and cardiovascular disease. The highest affinity target of resveratrol identified so far is the oxidoreductase enzyme quinone reductase 2 (QR2), which is believed to function in metabolic reduction and detoxification processes; however, evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Therefore, inhibition of QR2 by resveratrol may protect cells against reactive intermediates and eventually cancer. With the aim of identifying novel inhibitors of QR2, we designed, synthesized, and tested two generations of resveratrol analogue libraries for inhibition of QR2. In addition, X-ray crystal structures of six of the resveratrol analogues in the active site of QR2 were determined. Several novel inhibitors of QR2 were successfully identified as well as a compound that inhibits QR2 with a novel binding orientation.
Modified approach for preparing (E)-Stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
Smidrkal, Jan,Harmatha, Juraj,BudiSinsky, Milo,Vokae, Karel,ZIDEKc, Zdenik,Kmoniekova, Eva,Merkl, Roman,Filip, Vladimir
scheme or table, p. 175 - 186 (2010/07/10)
Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed as E-isomers only (using Wittig-Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-a were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.
Huazhongilexone is not 3′,5,5′,7-tetrahydroxyflavanone. Preparation of 3′,5′-dimethoxy-5,7-dihydroxyflavanone
Anthoni, Uffe,Encarnacion D., Rosalba,Nielsen, Per H.,Christophersen, Garsten
, p. 1243 - 1246 (2007/10/03)
Huazhongilexone, isolated from Ilex centrochinensis, was originally assigned the structure 3′,5,5′,7-tetrahydroxyflavanone. The racemic flavanone has been synthezised. Huazhongilexone is different from the synthetic compound and thus must have a different structure. In addition the new (±)-3′,5′-dimethoxy-5,7- dihydroxyflavanone has been prepared and characterized. Acta Chemica Scandinavica 1998.
Phenanthrene Synthesis: Coeloginin a Novel 9,10-Dihydrophenanthrene from the Orchid Coelogyne cristata
Sargent, Melvyn V.,Stanojevic, Edi
, p. 1919 - 1921 (2007/10/02)
The synthesis of 2,6-dihydroxy-7,8-dimethoxy-9,10-dihydro-5H-phenanthropyran-5-one (coeloginin) (1), a natural product isolated from the orchid Coelogyne cristata, is described.The key step involved the treatment of methyl 9,10-dihydro-5,7-di-iso
