143901-35-3Relevant articles and documents
Biomimetic kinetic resolution: Highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products
Stone, Steven D.,Lajkiewicz, Neil J.,Whitesell, Luke,Hilmy, Ahmed,Porco, John A.
supporting information, p. 525 - 530 (2015/01/30)
We have previously reported asymmetric syntheses and absolute configuration assignments of the aglains (+)-ponapensin and (+)-elliptifoline and proposed a biosynthetic kinetic resolution process to produce enantiomeric rocaglamides and aglains. Herein, we
Synthetic silvestrol analogues as potent and selective protein synthesis inhibitors
Liu, Tao,Nair, Somarajan J.,Lescarbeau, Andre,Belani, Jitendra,Peluso, Stephane,Conley, James,Tillotson, Bonnie,OHearn, Patrick,Smith, Sherri,Slocum, Kelly,West, Kip,Helble, Joseph,Douglas, Mark,Bahadoor, Adilah,Ali, Janid,McGovern, Karen,Fritz, Christian,Palombella, Vito J.,Wylie, Andrew,Castro, Alfredo C.,Tremblay, Martin R.
, p. 8859 - 8878,20 (2020/09/16)
Misregulation of protein translation plays a critical role in human cancer pathogenesis at many levels. Silvestrol, a cyclopenta[b]benzofuran natural product, blocks translation at the initiation step by interfering with assembly of the eIF4F translation complex. Silvestrol has a complex chemical structure whose functional group requirements have not been systematically investigated. Moreover, silvestrol has limited development potential due to poor druglike properties. Herein, we sought to develop a practical synthesis of key intermediates of silvestrol and explore structure-activity relationships around the C6 position. The ability of silvestrol and analogues to selectively inhibit the translation of proteins with high requirement on the translation-initiation machinery (i.e., complex 5′-untranslated region UTR) relative to simple 5′UTR was determined by a cellular reporter assay. Simplified analogues of silvestrol such as compounds 74 and 76 were shown to have similar cytotoxic potency and better ADME characteristics relative to those of silvestrol.
ASYMMETRIC SYNTHESIS OF ROCAGLAMIDES VIA ENANTIOSELECTIVE PHOTOCYCLOADDITION MEDIATED BY CHIRAL BRONSTED ACIDS
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Page/Page column 49, (2008/06/13)
The present invention provides a new strategies for the synthesis of compounds of the rocaglamide family and related natural products. The synthetic approach generally involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by an enantioselective 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile in the presence of a TADDOL derivative. This approach can be used for the formation of adducts containing an aglain core structure. Methods of the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.
