Journal of Medicinal Chemistry
Brief Article
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ASSOCIATED CONTENT
* Supporting Information
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S
Experimental procedures, characterization data, pharmacologic
data, biological methods. This material is available free of
AUTHOR INFORMATION
Corresponding Author
■
Present Address
§Department of Chemistry and Biochemistry, Florida Atlantic
University, 777 Glades Road, Boca Raton, FL, 33431, United
States.
Author Contributions
∥C.M.R. prepared compounds (+)-9 and (−)-9, 11−17, and
22−28, and composed the manuscript. R.C. performed
eukaryotic translation assays, RNA filter and affinity pull
down assays, animal studies, and composed the manuscript.
S.P.R. prepared compounds 7−10. J.P. and J.A.P., Jr., conceived
and directed the research and composed the manuscript.
ACKNOWLEDGMENTS
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We thank Dr. Layton Smith (Sanford-Burnham Medical
Research Institute) for pharmacokinetic studies of (−)-9. We
also thank Dr. Paul Ralifo (Boston University) for NMR
assistance. C.M.R. gratefully acknowledges a postdoctoral
fellowship from the American Cancer Society (PF-11-077-01-
CDD). R.C. gratefully acknowledges a postdoctoral fellowship
from the Cole Foundation. Funding is gratefully acknowledged
from the NIH (GM-073855 to J.A.P., Jr.) and the Canadian
Cancer Society Research Institute (17099 to J.P.)
ABBREVIATIONS USED
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DCC, N,N-dicyclohexylcarbodiimide; DMAP, 4-
(dimethylamino)pyridine; EDCI, N-(3-dimethylaminopropyl)-
N′-ethylcarbodiimide hydrochloride; HOBt, 1-hydroxybenzo-
triazole hydrate; MEK, mitogen activated protein kinase kinase;
NBS, N-bromosuccinimide; NCS, N-chlorosuccinimide; THF,
tetrahydrofuran; DMSO, dimethylsulfoxide; eIF4A, eukaryotic
initiation factor 4A; eIF4E, eukaryotic initiation factor 4E;
eIF4F, eukaryotic initiation factor 4F
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S.; Higa, T.; Belsham, G. J.; Wagner, G.; Tanaka, J.; Pelletier, J.
Functional characterization of IREDes by an inhibitor of the RNA
helicase eIF4A. Nature Chem. Biol. 2006, 2, 213−220.
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Targeting the eukaryotic translation initiation factor 4E for cancer
therapy. Cancer Res. 2008, 68, 631−634.
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