83768-75-6Relevant articles and documents
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.
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.
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