83768-75-6Relevant academic research and scientific papers
Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities
Arai, Midori A.,Kofuji, Yuuki,Tanaka, Yuuki,Yanase, Natsuki,Yamaku, Kazuki,Fuentes, Rolly G.,Karmakar, Utpal Kumar,Ishibashi, Masami
, p. 3061 - 3068 (2016)
Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3′-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.
Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors
Zhang, Wenhan,Chu, Jennifer,Cyr, Andrew M.,Yueh, Han,Brown, Lauren E.,Wang, Tony T.,Pelletier, Jerry,Porco, John A.
supporting information, p. 12891 - 12900 (2019/09/09)
Rocaglates are a family of natural products isolated from the genus Aglaia which possess a highly substituted cyclopenta[b]benzofuran skeleton and inhibit cap-dependent protein synthesis. Rocaglates are attractive compounds due to their potential for inhibiting tumor cell maintenance in vivo by specifically targeting eukaryotic initiation factor 4A (eIF4A) and interfering with recruitment of ribosomes to mRNA. In this paper, we describe an intercepted retro-Nazarov reaction utilizing intramolecular tosyl migration to generate a reactive oxyallyl cation on the rocaglate skeleton. Trapping of the oxyallyl cation with a diverse range of nucleophiles has been used to generate over 50 novel amidino-rocaglate (ADR) and amino-rocaglate derivatives. Subsequently, these derivatives were evaluated for their ability to inhibit cap-dependent protein synthesis where they were found to outperform previous lead compounds including the rocaglate hydroxamate CR-1-31-B.
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.
supporting information, 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.
AGENTS AND METHODS FOR TREATING DYSPROLIFERATIVE DISEASES
-
Paragraph 00132; 00136, (2019/09/04)
Compounds are described with the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, and n are defined as anywhere herein, which are useful for the treatment of cancer and other dysproliferative diseases.
An Attempted Synthesis of Multijuginol
Antus, Sandor,Boross, Ferenc,Giber, Janos,Kajtar-Peredy, Maria,Nogradi, Mihaly
, p. 995 - 1003 (2007/10/02)
(3RS,3aSR,8aSR)-2,3,3a,8a-Tetrahydro-3-hydroxy-4,6-dimethoxy-2,2-dimethylfurobenzofuran (29), a partial structure of the title substance 2, was synthesized in 11 steps from phloroglucinol, but could not be transformed into rac-2.Some partly unexpec
