117828-45-2Relevant articles and documents
COMPOSITIONS AND METHODS FOR INHIBITING VIRAL INFECTION
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Paragraph 0020, (2020/05/06)
Described herein are compounds, agents, compositions, and methods related to the treatment of a viral infection (e.g., Hepatitis C viral infection). In particular, the compounds, agents, compositions, and methods described herein inhibit viral entry into a target cell.
Chemical Synthesis Enables Structural Reengineering of Aglaroxin C Leading to Inhibition Bias for Hepatitis C Viral Infection
Zhang, Wenhan,Liu, Shufeng,Maiga, Rayelle I.,Pelletier, Jerry,Brown, Lauren E.,Wang, Tony T.,Porco, John A.
, p. 1312 - 1323 (2019/01/21)
As a unique rocaglate (flavagline) natural product, aglaroxin C displays intriguing biological activity by inhibiting hepatitis C viral entry. To further elucidate structure-activity relationships and diversify the pyrimidinone scaffold, we report a concise synthesis of aglaroxin C utilizing a highly regioselective pyrimidinone condensation. We have prepared more than 40 aglaroxin C analogues utilizing various amidine condensation partners. Through biological evaluation of analogues, we have discovered two lead compounds, CMLD012043 and CMLD012044, which show preferential bias for the inhibition of hepatitis C viral entry vs translation inhibition. Overall, the study demonstrates the power of chemical synthesis to produce natural product variants with both target inhibition bias and improved therapeutic indexes.
Synthetic analogue of rocaglaol displays a potent and selective cytotoxicity in cancer cells: Involvement of apoptosis inducing factor and caspase-12
Thuaud, Frédéric,Bernard, Yohann,Turkeri, Gulen,Dirr, Ronan,Aubert, Geneviéve,Cresteil, Thierry,Baguet, Aurélie,Tomasetto, Catherine,Svitkin, Yuri,Sonenberg, Nahum,Nebigil, Canan G.,Désaubry, Laurent
supporting information; experimental part, p. 5176 - 5187 (2010/03/02)
Flavaglines constitute a family of natural anticancer compounds. We present here 3 (FL3), the first synthetic flavagline that inhibits cell proliferation and viability (IC50≈1 nM) at lower doses than did the parent compound, racemic rocaglaol.
Total synthesis of (±)-rocaglamide and some aryl analogues
Dobler, Markus R,Bruce, Ian,Cederbaum, Fredrik,Cooke, Nigel G,Diorazio, Louis J,Hall, Roger G,Irving, Ed
, p. 8281 - 8284 (2007/10/03)
The insecticidal activity found for rocaglamide and its congeners, prompted us to establish a short and efficient synthesis of the natural product and some synthetic 'halo-aryl' analogues. Pd-catalysed cross-coupling reactions of the bromo analogue were then explored in order to gain a suitable access to a broad range of unnatural analogues. The key step of our approach is a keto-aldehyde acyloin ring-closure followed by a Stiles carboxylation.
Synthesis of the Novel Anti-leukaemic Tetrahydrocyclopentabenzofuran, Rocaglamide and Related Synthetic Studies
Davey, Andrew E.,Schaeffer, Marcel J.,Taylor, Richard J. K.
, p. 2657 - 2666 (2007/10/02)
Two approaches to the rocaglamide tricyclic skeleton are described.The first, which employs an unusual dithianyl anion to carbonyl addition reaction, provides access to α-phenyl rocaglamide analogues.The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both α- and β-phenyl substituents.A total synthesis of rocaglamide, in racemic form, is described using this second approach.The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield > 6percent.The synthesis of 1-epi-rocaglamide 29b is also described.
A Synthetic Approach to Rocaglamide via Reductive Cyclization of δ-Keto Nitriles
Kraus, George A.,Sy, James O.
, p. 77 - 83 (2007/10/02)
The anticancer agent rocaglamide contains a novel bicyclooctanol structure.The approach to this molecule involved the preparation of a hydroxy ketone intermediate via a samarium-mediated cyclization.This ketone was then converted into an excellent
