Relevance of the C-5 position to schweinfurthin induced cytotoxicity

Joseph J. Topczewski, Michael P. Callahan, John G. Kodet, Jery D. Inbarasu, Nolan R. Mente, John A. Beutler, David F. Wiemer

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay.

Original languageEnglish (US)
Pages (from-to)7570-7581
Number of pages12
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number24
DOIs
StatePublished - Dec 15 2011

Bibliographical note

Funding Information:
We thank the ACS Division of Medicinal Chemistry for support in the form of a predoctoral fellowship (to J.J.T.), the University of Iowa Department of Chemistry for a Shriner Fellowship (to J.J.T.), the UI Graduate College for a Presidential Fellowship (to J.G.K.), and the Iowa Center for Research by Undergraduates for a summer fellowship (to J.D.I.). This research was supported in part by the Intramural Research Program of NIH, National CancerInstitute, Center for Cancer Research. Financial support from the Roy J. Carver Charitable Trust as a Research Program of Excellence is gratefully acknowledged.

Keywords

  • Anti-proliferative
  • Apoptosis
  • Bioassay
  • Cytotoxic
  • Schweinfurthins

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